The Terrible Catsafterme

SEASON 1 – NBC

Theme music composed by Jonathan Wolff

• 001. Pilot (aka Love and Marriage) – 9/21/1998
  • Lawyer Will Truman (Erik McCormack) and interior designer Grace Adler (Debra Messing) are best friends living separately in New York. Will is recently out of a long-term homosexual relationship and Grace is living with her boyfriend Danny. After a fight, Grace decides to stay the night with Will, which precludes Will’s other gay friend Jack McFarland (Sean Hayes) from moving in temporarily while his apartment floors are being refurbished. She then tries to break it off with Danny, but he unexpectedly proposes to her and she accepts. She is encouraged to stay with Danny by her ultra-rich assistant Karen Walker (Megan Mullally), but Will can’t hold his tongue and eventually tells Grace that a marriage to Danny would be a serious mistake. This initially infuriates Grace, but eventually she comes to realize that his advice was heartfelt and the two resume their friendship. Gary Grubbs stars as Will’s biggest client Harlin Polk. Tom Gallop and Leigh-Allyn Baker star as friends Rob and Ellen. 4/15/13

• 002. A New Lease on Life – 9/21/1998
  • Grace is halfheartedly searching for new apartments, but holding out hope that Will might let her move in with him. Will steadfastly refuses to allow her to move in, although Jack and his bird Guapo are driving him crazy. Grace eventually finds an apartment in Brooklyn. Will is initially excited, but then concerned that Grace would be too far from his place in Manhattan. After Grace signs a two-year lease, Will asks Grace to move in with him – but she responds that it is too late. After getting all of her stuff moved in, at the last minute she changes her mind and shows up at Will’s apartment with a suitcase. Meanwhile, Jack and Karen meet at Grace’s office for the first time and hit it off immediately. 4/16/13

• 003. Head Case – 10/5/1998
  • Prompted by Jack’s comments that Will is too rigid in relationships, Will agrees to let Grace expand their two small bathrooms into one large one. This and other changes that Grace is making around the apartment begins to grate on Will’s nerves, and a visit from Harlin leads to even more tension. Will decides that having Grace live with him is not a good idea because he knows he is too selfish and that it has destroyed his past relationships – but then has a change of heart and decides to move the bathroom wall over so that they have equal size bathrooms. 5/12/13

• 004. Between a Rock and Harlin’s Place – 10/12/1998
  • Will arranges for Grace to decorate Harlin’s New York apartment with the promise not to interfere, but when she goes ‘over the top’ with a Texas cowboy theme, Will speaks up about his disdain for it. Harlin ends up firing Grace, but when Will finds out that she was fired because it was leading to tension between he and Grace, not because he didn’t like the decor, Will is forced to apologize and make a pact not to butt into Grace’s business. Jack decides to pursue a career as a cabaret singer and performs he show ‘Just Jack’ at open mic night at a local club. 5/12/13
• 005. Boo! Humbug -10/26/1998
  • Will and Grace both dismiss Halloween as a kids’ holiday, so Jack goes to the downtown gathering with Karen as Body & Soul – that is, David Soul. Karen enjoys herself once she is mistaken for a drag queen, and Jack meets the ‘Starsky’ to his ‘Hutch’. Harlin has to negotiate a deal so he drops his son and daughter – dressed as Richard Nixon and a bumblebee – for Will to babysit, disrupting the Ingmar Berman marathon that he and Grace were about to have. When feeding the kids Clamato and offering to share their Berman films doesn’t work, Will and Grace take the kids trick or treating in the building. Although Will’s prospect of flirting with one of the guys is stymied by the fact that they all  look like a family, everyone seems to enjoy the evening which culminates in a silly string fight. Paul Goebel appears as one of the tenants. 1/10/14
• 006. William, Tell – 11/9/1998
  • With Karen going on vacation, Grace asks Jack to fill in as her replacement. While debating on which one knows more about Will, Jack tells Grace of an affair that Will had with a man named Steve whom Will always referred to as a ‘client’. This causes Grace to suspect that Will is having another affair and not telling her, so she snoops in his planner and finds out that he is meeting someone named ‘K’ for dinner. Grace follows him and finds out that he is actually meeting Karen, who is looking for legal advice because she is considering divorcing her husband Stan. Will chastises Grace for snooping into his private life, and Grace reveals that she is always worried that he will drop another bomb on him similar to when he came out of the closet. 1/10/14

• 007. Where There’s a Will, There’s No Way – 11/16/1998
  • Grace has no sex drive whatsoever and she blames Will because she has too much fun with him to have any use for a relationship. She puts a moratorium on their ‘fun’, but quickly finds that she still has no interest in anyone. Once she realizes this, she tries to join a poker game with Will, Jack, and Karen, but Will stubbornly refuses to allow her. Eventually they reconcile, and Will notes that it’ll happen when it happens… just before she becomes smitten with a man on the elevator. Meanwhile, Jack is being pursued by the I.R.S. having never paid taxes. Will helps him out with the auditor (Roy Fegan) and then agrees to pay the $2000 for Jack. Steve Paymer is Steve. 1/27/14

• 008. The Buying Game – 11/30/1998
  • Grace has a chance to purchase her studio from British seller Mr. Hutt (Ivar Brogger) and looks to Will for guidance on the negotiation. Hutt gets Grace to sing a deal with Will not around, but Will says she got swindled. Will shows up for another meeting with Hutt, and is able to get what he believes to be the ‘floor’ of the negotiated price, but not without insulting Grace and telling Mr. Hutt that he took advantage of someone with no business sense. This infuriates Grace and causes her to break down crying at the signing and nearly backing out. Hutt then goes even lower to appease Grace, and she takes delight in the fact that she worked him for less than Will did. Meanwhile Jack practices to be a massage therapist on Karen, who likes his work so much that she hires him to be her own personal masseuse. Jack quits the arrangement because he doesn’t want their association to be all business…as it would if he were a straight man. 1/27/14
• 009. The Truth About Will and Dogs – 12/15/1998
  • After some friends brag about their dogs, Grace goes out and gets Will a dog despite Will’s objections. In a matter of seconds, Will falls in love with it and becomes utterly obsessed with its care, insisting that they alternate taking the dog to work each day. Grace feels they need a night out together so she has Jack and Karen come over and babysit the dog. Jack enjoys walking him and meeting cute guys in the park, while Karen just drinks and goes through Grace’s closet. Will can’t enjoy himself because he is worried about the dog, and they come home early. Grace thinks Will needs to get back in the dating game instead of directing his love toward the dog. Will ultimately agrees and gives the dog to Jack. 2/23/14
• 010. The Big Vent – 1/5/1999
  • Will gets the heating vent in the cold apartment fixed, and while hovering over it, Will and Grace discover that they can hear the downstairs neighbors’ unfolding drama. They both become so fixated on the affair that ‘Ooie’ Judy (Corinne Bohrer) is having with her husband Thomas’ (T.F. Sullivan) brother Dennis that they blow off Jack on several occasions. Meanwhile, Jack has been taking a screenwriting class and has written a play called Love Among the Coconuts: A Caribbean Fantasy. Karen thinks it’s terrible and advises him to write about people he known. Will and Grace take a break from the eavesdropping to make an appearance at Jack’s revised play, which turns out to be about Will (Robert Curtis Brown) and Grace (Jensen Daggett) attending the funeral of Jack. They realize they’ve treated Jack poorly and bring him back to their apartment to give him some of Will’s suites. Thomas and Judy are listening through the vent below and feeling better out their own problems. Titus Napoleon is Roger Waka-Lana-Huki. 2/23/14
• 011. Will on Ice – 1/12/1999
  • It’s Will’s birthday and he laments on past birthday disappointments, telling both Jack and Grace that all he wants is for the two of them to get along. They end up bonding over their love of ice skating, in which Will has no interest. Karen managed to finagle seats at Balthazar restaurants, but when Jack gets tickets to Champions on Ice, Will agrees to skip the dinner and go to the ice production to make them happy. At the show, Karen give Will alcohol and gets him to confess that he always makes other people happy on his birthday and never gets want he wants, and he ends up leaving. Grace surprises Will with the cowboy cake he always wanted, and Jack ends up going on a date with ice skater Rudy Galindo (as himself). 5/18/14
• 012. My Fair Maid-y – 2/2/1999
  • Grace is a nervous wreck as she prepares for her entry into the Sublime Design contest to be judged by design critics. She is letting the apartment go, so Will hires a maid for her named April (Wendie Jo Sperber), who manages to inspire her to do her best creating by giving her stress relief tactics that include screaming. Grace becomes obsessed with having the maid around, but Will thinks it is unhealthy and pays April not to come back. Grace freaks out until she finds out that a major design critic (Burt Goodman) thinks she is brilliant. Meanwhile, Jack meets a man named Alex (Raphael Sbarge) and pretends that he is a lawyer and that Will is his assistant. Alex ends up breaking up with Jack and showing interest in Will because he thinks Jacks has it ‘too together’ for his tastes. 5/18/14

• 013. The Unsinkable Mommy Adler – 2/9/1999
  • Grace’s mother Bobbi (Debbie Reynolds) comes for a visit, and Grace dreads seeing her because she always tries to be the center of attention. Although Grace thinks she will criticize Grace for living with a gay man, Bobbi actually says she likes Will and wishes that she and Grace would get married. Will and Grace both laughs at the notion, and Will mentions that he couldn’t marry Grace even if he were straight, the reason being that she needs to be the ‘star’ of the relationship. Grace realizes that she is more like her mother than she chooses to believe, but her mother helps her comes to terms with it. Karen thinks that she might be pregnant, and is clearly sad when she finds out she isn’t – so Jack offers some emotional support. 8/9/14

• 014. Big Brother Is Coming: Part 1 – 2/16/1999
  • While shopping for Jack’s surprise birthday party – which is not really a surprise at all – Grace runs into Sam (John Slattery), Will’s estranged brother. The two haven’t spoken in years since Will told Sam that he doesn’t like nor approve of the woman who Sam was planning to marry. The two did end up getting married, but are now going through a divorce. Grace gets Sam to come to Jack’s party, and the bickering between him and Will take the attention of Jack, much to his chagrin. After spending hours unveiling all of their deep-rooted feelings, the brothers finally reconcile. After Will leaves the apartment, Sam and Grace share a passionate kiss. NOTE: This is the first of a two-part episode. 8/9/14

• 015. Big Brother Is Coming: Part 2 – 2/23/1999
  • Grace sleeps with Sam twice and although she tries to tell Will about it, he is wrapped up in a computer dating site where he has met a dentist. Karen can see it written all over Grace’s face, and although she promises on her jewelry to keep it a secret, she tells Jack about it. When Sam tells Will that he is seeing someone, Will finally puts it together and explodes in anger, spouting off how Sam steals everything that belongs to him. Grace takes exception to be being referred to as one of Will’s ‘toys’. Karen tells Grace that she only went for Sam because he is the straight version of Will, and Jack explains to Will that he is jealous that Sam has a part of Grace that he can never have. Will and Grace make amends, and Grace ends it with Sam. NOTE: This is the second of a two-part episode. 9/14/14

• 016. Yours, Mine or Ours – 3/2/1999
  • Grace and Will each meet Peter (David Newsom), a new tenant in their apartment, and each makes a date with him to attend his housewarming party. They agree that whenever they can figure out whether he is gay or straight the other will step aside. They spend the evening receiving his mixed signals, each one thinking that he is going for them. They try to employ Jack’s ‘gaydar’ but he has trouble figuring it out from the information given – although once he meets Peter, he claims to know. Finally them simply ask Peter if he likes men or women, but Peter is incredulous and leaves with only the vague comment “you’re not my type,” leaving Will and Grace each to think that it was the other person who was dumped. They agree never to go after the same man again. Meanwhile, Grace has to fire her driver (Earl Schuman) because he is too old to drive. 9/14/14

• 017. Secrets and Lays – 3/23/1999
  • Will, Grace, and Jack join Karen at her cabin retreat in Vermont for a winter weekend, which Grace has set up to help Will forget the anniversary of him and his former boyfriend Michael. The caretaker delivering wood turns out to be Campbell (David Stucliffe), a former flame of Grace’s from high school. Sparks fly immediately, but Grace refuses to go out with him because the weekend is about keeping Will occupied. She sneaks off with him briefly after Will goes to bed and they kiss. While playing Monopoly, Will realizes what the weekend is about and scolds Grace for thinking he is so fragile. The next night Jack take Will to a gay bar, but Will comes home early and Grace hides Campbell out in the cold. Will is furious that Grace can’t even share her new fling with him…but finally does acknowledge how upset he is and how much he misses Michael. 10/16/14

• 018. Grace, Replaced – 4/8/1999
  • Grace is working a lot of overtime and consequently has no time for Will, who meets a new tenant named Val (Molly Shannon) and hits it off with Will immediately. Will and Val become inseparable, and Karen feels like she is moving into Grace’s territory. Grace becomes even more irritated when she comes home to find that Will and Val have tied Will and Grace’s score in the game Pyramid. When Grace finds out that Will is home sick and that Val is taking care of him, she rushes home to relieve Val. The two end up in a clothes-ripping fistfight, but cooler heads eventually prevail and Grace and Val become friends. Meanwhile, Jack is forced to clean up trash for community service imposed after he slaps a meter maid. Among the trash, he finds Soon-Yi Allen’s phone bill and he and Karen make prank calls to her. 10/17/14

• 019. Will Works Out – 4/22/1999
  • When Jack gets kicked out of his gym, Grace offers him Will’s “Buddy Pass” much to Will chagrin. Will is clearly worried about being embarrassed, particularly with some of his clients attending the gym. When client Richard Keller (Ben Reed) shows up, Will pushes Jack aside. Both Jack and Grace assume that Will is “jock blocking” him, but Will tells Grace that it is because Jack acts like such a ‘fag’…which Jack overhears. Jack tries to act manly during his next visit, and tells Will that he overheard him. Grace reminds Will that Jack is his best friend, so Will apologizes, introduces him to Richard as his friend, and buys Jack a gym membership. Meanwhile, Karen, who is having trouble with Stan, spends a night at Grace’s apartment drinking. When Will and Jack return, they find Grace passed out on top of Karen, noting that the sight is wasted on them. 11/11/14

• 020. Saving Grace – 4/29/1999
  • Grace interviews with wealthy and arrogant publicist Nathan Berry (Miguel Ferrer) to decorates his apartment, bringing Karen along with her. He nearly dismisses Grace until he finds out he knows Karen, then agrees to see Grace’s apartment to make sure it is decorated to his satisfaction. While there he meet Will and develops an obvious crush on him, making a deal with Grace that she can have the job if she gets Will to go on a date with him. The date goes miserably with Nathan rude to both Will and the waiter (John Balma), but Wills straightforwardness is a turn-on for Nathan and he asks Grace to get him a second date, agreeing to double her budget if he does. Will refuses, and Karen convinces Grace that her talent is more important that she realizes. Grace regains her confidence, but Will agrees to another date with Nathan…but then pretends that he’s ready to move in with him. Nathan then dismisses Will, but continues utilizing Grace as his decorator. 11/13/14

• 021. Alley Cats – 5/6/1999
  • After a particularly brutal game of Charades, Rob and Ellen confess to Will that they can’t stand playing games with Grace. When she finds out, she is offended that they only think she has a competitive side and not Will. Later during a bowling match, Rob and Ellen are winning, but Grace seems to be having fun even though she is bowling terribly. Will finally reaches his breaking point and has to admit that he is just as competitive and enjoys Grace’s obnoxious behavior when destroying Rob and Ellen at games. After Stan gives Karen a scare by choking in a restaurant, she has Jack teach her CPR. She actually has to utilize it, much to her chagrin, when Bernie (John Capodice), a man working on the heater in Grace’s office, has a heart attack. She saves his life, but both her and Jack seem more interested in having the attractive paramedic (Lucky Vanous) perform CPR on them. 12/27/14

• 022. Object of My Rejection – 5/13/14
  • Will is very vocal when he finds out that Grace is going on a date with her ex-fiancee Danny (Tom Verica), but Grace tells him that he needs to butt out, and Jack and Karen both agree that he needs to get his own life. Grace continues her relationship with Danny, and all the while seemingly prods Will for his opinion, while Will remains frustratingly silent. Meanwhile, Karen’s maid Rosario Salazar (Shelley Morrison) – with whom she shares a constant love/hate relationship – is going to be deported back to El Savador unless she gets married. For $1000, Jack agrees to be the ‘bride’ groom, and the two are married. At the ceremony, Grace continues to prod Will, who finally blows up when she says she is falling in love with Danny. Grace then confesses that she broke it off but was trying to get Will’s opinion. The two then share a kiss and have a heartfelt admission that they are too involved in each other’s lives. They agree that Grace needs to move out. Franklin Cover is the minister. The show’s producer Steve Sandoval appears as the church janitor. 12/28/14

SEASON 2

• 023. Guess Who’s Not Coming to Dinner – 9/21/1999
  • Will helps Grace move into her new apartment, which is revealed to be directly across the hall from Will. When Grace keeps barging into Will’s apartment, frequently interrupting his naked time, he accuses her of being too dependent on him. Grace then arranges a dinner party picnic in her apartment which bores her guests Karen, Rob, and Ellen to tears. Will barges in to the party needing advice on whether his date Richard (Keith Biele) has blown him off, and Grace turns the tables by demanding that they stay independent of one another. She decides to find another apartment so they can be more independent, but when she finds that Will has Richard over, she realizes they both still can rely on each other but also do their own thing. Meanwhile Jack moves into Rosario’s room at Karen’s house because the INS threatens to do random checks to see if their marriage is legitimate. 2/14/15

• 024. Election – 9/28/1999
  • Grace is unhappy that her chimney has been sealed up and Will’s has not. She is even more irritated by his cockiness as president of the tenant’s association and decides to run against him. The both campaign heavily and it the vote ends up being a tie because member Mr. Munitz (Ralph Drischell) is in the hospital. They both visit him there while and plead their cases, and he wearily elects Grace. However the job turns out to be less than glamorous and Will has the last laugh. Meanwhile Karen accidentally lets Jack’s bird Guapo fly out the window. To console him, she take him on a shopping spree. Even though Guapo comes back, Jack hides him in the closet to keep getting gits. When Karen gives him a boat he ends up confessing, which she already knew thanks to hidden cameras. The keys to the boat turn out to be to Grace’s office. Lou Cutell and Shirley Prestia play Mr. and Mrs. Arthur Pressman. Marshall Manesh is Mr. Zamir. 2/14/15

• 025. Das Boob – 11/2/1999
  • Grace appears in a newspaper article about one of her designing jobs and the photo of her makes her breasts appear larger than they are. When old high school crush John Gregorio (Scott Patterson) calls Grace and invites her his art show, she and Karen assume it is because he thinks she is more endowed than she is. Meanwhile Jack finds out that Will had a fling with his ex-boyfriend Walter (Anthony DeSantis) and starts to snub Will and threatens to end their friendship. Grace attends the show wearing a hydro bra. John seems attracted to her, but when her bra springs a leak and he finds out that they are fake, he accuses her of being shallow and then proceeds to hit on Karen. Grace douses his artwork with her bra water. Will gets Jack to attend the show by telling him that Cher will be there, but then surprises him by having Walter show up. However Jack then realizes that Walter wasn’t the same guy he thought he was. 3/23/15

• 026. Whose Mom Is It Anyway? – 11/9/1999
  • Grace’s mother shows up with guy named Andy Fellner (Andy Comeau) who Grace knew back in grade school and Grace assumes that she is trying to set her up again. Will is amused by the situation until he realizes that Andy is meant as a date for him. Grace forces him to go through with the date in order to show her mother what a poor matchmaker she is. The plan backfires when Will really likes Andy. Grace is livid and ruins their date, but eventually admits that she is actually upset because her mother has stopped fixing her up, even though Grace had told her to. Meanwhile Jack and Rosario have to meet with INS agent Roger O’Neil (Peter Paige) who was a former fling of Jack’s. He is ready to deport Rasario, until Jack declares his love and plants a passionate kiss on her… after finding out that Karen really thinks of Rosario as a friend. 3/23/15

• 027. Polk Defeats Truman – 11/16/1999
  • Will makes a heap of money when he closes one of Harlin Polk’s deals. With Polk as his number one client, he begins to drop some of his others, much to the irritation of Grace who thinks that Will’s success has gone to his head. When Harlin ends up firing Will in order to get more high-powered lawyers for his expanding business, Will tries to keep it a secret so that Grace will not gloat. Meanwhile Karen cashes all of her payroll checks and forces Grace’s bank account into hole. Stan has put Karen on a budget, but Grace offers to coach her on being thrifty if she will put the money back into the account. Karen fights her tooth and nail, and when she tells Stan that she is going to be wearing cheap clothes for their next event, Stan calls off Karen’s budget. Grace runs into Harlin who tells her that he has fired Will. Grace comforts Will without being judgmental, as he has to start over in his career. 6/29/15

• 028. To Serve and Disinfect – 11/23/1999
  • As Will moves out of his office, Jack gloats about being promoted to captain at his catering company. Will thinks his job is easy so Jack wagers him that Will can’t handle serving at an engagement at the Waldorf-Astoria. Will accepts the challenge, but once there, he realizes that he will be serving members of the American Bar Association that he knows. Will abandons Jack and sits with his old friends, but when one of them, Brian Kelly (Brian Palermo), gets rude with Jack, Will comes to his defense and returns to working for Jack. Meanwhile a fax machine repairman named Brent (Kim Robillard) tells Grace that he recognizes Karen from a porn film called Next to Godliness. Karen is upset that Grace now has leverage on her and storms out, heading the the producer of the film, Carl (Terry Kiser) to try and get copies of the film back with no luck. Karen tells Grace that she is going to have to quit, only to find that Grace has scoured the city and purchased every copy of the film to avoid Karen’s embarrassment. 6/29/15

• 029. Homo for the Holidays – 11/25/1999
  • Will has invited Jack’s mother Judith (Veronica Cartwright) to spend Thanksgiving with them, much to Jack’s chagrin. When Judith pays Will a visit, he and Grace realize that Jack has told his mother that Grace is an ex-girlfriend, and furthermore has never told her that he is gay. Will and Grace convince him that he has to tell her, but Jack has too much anxiety about how she will react. Will finally reminds him how Jack had pressured Will into coming out a long time ago, and returns the advice to Jack. Judith is shocked but understanding, and then lays a secret on Jack: that his father is not really his natural father, but that he was the result of a key party. 8/8/15

• 030. Terms of Employment – 11/30/1999
  • Grace has a client named Ben Doucette (Gregory Hines) back out of his contract to have her redecorate after having spent a huge chunk of money on materials and looks to Will to help her go after him legally. Will has been out of work for two months and is nervous about taking a case against Ben, because he happens to be a high profile lawyer. Ben ends up impressed with Will and offers him a job at Doucette & Stein, which Grace believes will make it easier to help her get her money. Ben however insists that the case go to arbitration with Will getting Ben out of paying the bill. At the last minute, Will switches to Grace’s side during the arbitration. Ben gives grace the money and surprises Will by telling him that this was exactly what he was looking for, someone with more scruples than him. Meanwhile Jack gets a job filming a sexual harassment training video for the Canterville Plate Glass Company with director Bob Dent (Robert Clendenin) and is forced to enlist Karen as his co-star when the actress calls in sick. It takes 148 takes to get it right because Karen keeps getting too turned on during the scene. Dan Sachoff is the video announcer. Jo Marie Payton is Ben’s secretary Mrs. Freeman. Aaron Lustig is arbitrator Marv. 8/11/15

• 031. I Never Promised You an Olive Garden – 12/14/1999
  • Will and Grace become bored with their friends Rob and Ellen, especially when they won’t go beyond their comfort level at a Japanese restaurant and insist on going to the Olive Garden. They happen to meet a new couple named Tai (Steve Valentine) and Naomi (Tamlyn Tomita) at the Japanese restaurant after Rob and Ellen leave, and end up lying to to their old friends by saying Will is sick in order to attend an Elvis Costello concert with their new friends. Things get awkward when Rob and Ellen show up at Will’s apartment as they are about to leave with their new friends, and after much scrambling around, Will and Grace are caught in their lie. However after Tai and Naomi keep them out all night getting drunk, Will and Grace decide they need a less exciting night so they catch up with Rob and Ellen at the Olive Garden. Meanwhile Jack accompanies Karen to her son’s grammar school for a meeting, despite his horrible memories of being picked on at that age. Jack ends up befriending a boy named John (J.T. Larsen) who is very similar to Jack and being picked on in a similar way. 11/16/15

• 032. Tea and a Total Lack of Sympathy – 1/11/2000
  • Ben gives Will one week to bring in a major client in order to keep his job at his law firm, and when Ben finds out that Will knows Karen, he tells him how much he’s always wanted to represent Walker Inc., run by Karen’s husband Stan. Will tracks down Karen and gets drunk with her, but when she finds out what he’s up to, she forces him to perform I Honestly Love You in the piano bar. Will stops in the middle, lays into Karen, and walks out… but she still signs up Walker Inc. with the law firm. Meanwhile Grace and Jack go on the show Antiques on the Road simply to meet the show’s host Porcelain Paul Archambreau (Harry Van Gorkum). But when the chintzy teapot she brings on the show ends up being worth $30,000, Grace and Jack argue over who gets the money. As Grace chases Jack around the studio, they crash through a shōji valued at $25,000. Porcelain Paul gives the shōji owners the teapot. David St. James is Smitty. Connie Sawyer is the old woman. 11/16/15

• 033. Seeds of Discontent – 1/25/2000
  • Will’s old friend Claire (Megyn Price) from high school, whom he refers to as ‘Grace before Grace’, comes home from France and visits with Will and Grace. She tells Will that she wants to have a baby and asks Will if he would be the sperm donor. Will shares the news with Grace, and although she acts excited, she falls apart when he leaves. When Grace tells Karen, she speculates that Grace has always considered Will as her ‘Plan B’ when it comes to having a baby and this is why she feels jealous. Will tells Claire that he will do it, and she asks him to visit the fertility clinic that day before she has to leave. Grace barges in and interrupts him at the clinic and opens up about her feelings. Will kicks her out for being selfish and not considering the happiness of Claire or how he feels. Grace later apologizes, but Will tells her that he couldn’t go through it because he has always considered Grace to be his ‘fallback egg’ too. Laura Kightlinger is a nurse. 1/11/16

• 034. He’s Come Undone – 2/8/2000
  • Will is having erotic dreams about Grace, and Jack advises him to see a psychiatrist. Dr. Loranger (Markus Flanagan) advises will that the dreams are probably not about sex, but about an unresolved issue with Grace, and advises Will to bring Grace to the next session. Grace ends up merely talking about herself the entire time, and then begins dating the doctor unbeknownst to Will. Eventually Will figures it out when Loranger keeps looking for hints about how to make Grace sleep with him. Will realizes that his issues with Grace are that she makes everything about her, including dating his shrink. Will resolves this by making sure he talks himself, but clams up when Grace asks him about his dreams. Meanwhile Jack starts snubbing Karen because of her poor treatment of Rosario, and eventually convinces Karen to treat her with respect. When Rosario finds out, she threatens to quit if Karen doesn’t stay nasty so they resume their bickering. Jack ends up having a dream about Will and Grace being passionate, while Will dreams of Stone Phillips (himself). 3/23/16

• 035. Oh Dad, Poor Dad, He’s Kept Me in the Closet and I’m So Sad – 2/15/2000
  • While Grace laments the poor relationship she has with her father, and Jack laments not knowing who is father is, Will’s father George (Sydney Pollack) comes for a visit. He and Will get along wonderfully, leaving Grace and Jack jealous, but he refuses Will’s offer to come to a work dinner where he will be receiving a Lifetime Achievement Award. Will and Grace go to the dinner anyway, and find out that George has never told his colleagues that Will is gay, and they all believe that he is married to Grace. Will confronts him and finds out that he is just too afraid that people will judge him. However when he receives his reward, his speech revolves around revealing the Will is gay and telling stories about him. Meanwhile Karen finds Jack’s father John Marshall (Perry King) for him and arranges a meeting. However it turns out that not only is John not actually the father, but he is also gay and he and Jack seem to have chemistry together. Mark Ankeny is Ted Farmer. Mimi Cozzens is BJ, and Joe Ochman is Chuck. 1/14/16

• 036. Acting Out – 2/22/2000
  • Jack is extremely excited to see two gay men kiss on national television on the sitcom Along Came You. However at the time of the pivotal kiss, the camera pans away, upsetting Jack beyond measure. Jack plans to complain to NBC, but Will wants no part of it until Grace reminds him that he is Jack’s friend and that if it is important to Jack, it should important to him. Meanwhile Grace is annoyed by her kind and sensitive boyfriend Josh (Corey Parker), and at Karen’s insistence, Grace plans to break it off. Karen suggests taking the easy way out and telling Josh that she is in love with Will. Jack and Will storm NBC and are told by a the president’s assistant Craig Fissay (Jeff Blumenkratz), who himself is a closet gay, that NBC has a responsibility to their viewership and there will never be a gay kiss on TV. Jack decides to appeal to Al Roker (himself) who is doing the weather outside in New York City. Will sees the opportunity to put a gay kiss on network TV and plants one on Jack, who mistakes the kiss for Will’s suppressed feelings toward him. It also ruins Grace’s excuse for dumping Josh, as they both watch the kiss on TV together. Amy Crofoot is the NBC receptionist. Mary Pat Gleason is Sally, the crazy lady who is petitioning to bring Johnny Carson back. 3/23/16

• 037. Advise and Resent – 2/29/2000
  • Ben, who has now becomes friends with Jack and refuses to apologize to Grace, sets Will up on a date with a Scottish man named Charlie (Michael E. Rogers), with whom he hits it off right away. However when Charlie doesn’t call him, Will starts to believe that he is a bad date. Meanwhile Grace feels smothered by her over-attentive boyfriend Josh. Karen advises her to withhold sex to get him to behave how she wants, and Grace actually takes the advice. Josh ends up breaking it off with her. After Will and Grace each share their woes, Jack attempts to tutor Will on how to date. Grace resents Karen’s bad advice, and eventually Josh gives Grace a second chance. Will realizes that he just as easily could have called Charlie when Jack points out his arrogance. He and Charlie run into each other and hit it off again. Kathleen Archer is the delivery woman. Brian Gattas is the waiter. 6/26/16

• 038. Hey La, Hey La, My Ex-Boyfriend’s Back – 3/7/2000
  • Will is beside himself when he finds out that his ex-boyfriend Michael (Chris Potter) is back in Manhattan and has contacted Grace to help design his new apartment. Karen wants to help decorate his apartment, but Grace only has the confidence to let her decorate one chair. Will runs into Michael and have an awkward encounter that leads Will to believe that Michael still has feelings for him. Will goes to see him and finds out that he is living with his boyfriend Andrew Kirkland (Christian Zimmerman). Will is embarrassed by the encounter, and even more livid at Grace when he finds out that she knew Michael was in a relationship. Jack tries to cheer up by bringing Will a sailor. Will and Grace talk out their issues, and she assures him that he’s not easy to get over. 6/26/16

• 039. The Hospital Show – 3/28/2000
  • Will goes on a date with an obnoxious guy named Neil (Dan Bucatinsky), who is a friend of his mother’s, but has Grace call with a fake emergency. Grace calls, but it turns out that she calls with a real emergency when Stan has a heart attack. Dr. Osher (Reginald C. Hayes) informs Karen that Stan only has acute angina, but didn’t have a heart attack, and he also tells Karen that her friends have made a wager on who Karen will break down in tears to first. Karen decides to have fun with them by asking Grace for blood despite her intense fear of needles with the inexperience trainee Nurse Pittman (Jennifer Elise Cox), Rosario to clean the hospital, Jack to cut up his credit cards, and Will to continue dating Neil, who followed Will to the hospital. Karen then reveals that she had been messing with them, tells them that she doesn’t do emotions, and throws him out. However Grace then finds Karen crying over having nearly lost Stan and comforts her. Lindsey Fields and Jennie Fahn appear as nurses. 9/19/16

• 040. Sweet and Sour Charity – 4/4/2000
  • Grace promises God that she will ‘worth His while’ if she and Will win a radio contest for front row Joni Mitchell concert tickets. When she wins, she talks Will and Jack into helping her donate to a charity for the homeless. Jack visits Karen’s massive closet to find something to donate, but Karen struggles to find anything she can part with. Will and Grace visit Sister Robert (Debra Mooney), and she advises them to work a charity bazaar to direct a kids’ production of Stone Soup. After working with the kids, Sister Robert informs them that the play will now be performed later which will cause them to miss the concert. Although Will thinks they should continue with the play, Grace tries to train the girl playing the carrot (Megan Taylor Harvey) to do Grace’s part of the narrator. Will gets irritated and sends Grace off to the concert. Grace shows up to complete the play, afterward admitting that she was kicked out by Joni for singing too loudly. Karen flips out when she finds out that Jack has given away her favorite pumps and drags him to the church bazaar to find them. They are nearly taken by a homeless woman named Sally (Mary Pat Gleason) but Grace offers her $500 for them. Sally thinks she’s offering five dollars and excitedly accepts. Grace feels bad and ends up giving her the $500 anyway. Daryl Sabara is the broccoli, Atehan Kihara is the radish. Richard Wharton is Gerald, the homeless man. 9/19/16

• 041. An Affair to Forget – 4/18/2000
  • Rob and Ellen announce that they are getting married, and furthermore ask Will and Grace to be their Best Man and Maid of Honor. They both agree, but Grace feels funny about it since she once slept with Rob when he and Ellen were on a break. Will plans the bachelor party with Jack’s help and he brings in a female cop stripper named Carla (Gretchen German). Neither of Rob’s friends Ira (Jim Ortlieb) nor Steve will take a lap dance from the stripper, so Jack steps in. He becomes concerned when it arouses him… until he finds out that Carla is really Carl from the waste down. Grace throws the wedding shower for Ellen and her friends Poly (Jennifer Manley) and Annette (Michele Gregory), but overhears Will and Grace talking about what Rob did with Grace and calls off the wedding. Ellen tries to even the score by sleeping with Will, but he refuses. Finally Rob goes over and and gets passionate with Ellen, causing her to forgive him and Grace. 12/13/16

• 042. Girls, Interrupted – 5/2/2000
  • With Will and Jack heading out to a gay bar alone, Grace turns to Val to keep her company. They get along swimmingly until Grace realizes that her music box is missing. Will finds it obvious that Val took it, but Grace doesn’t want to believe it. She and Will end up breaking into Val’s apartment and find the box. Val returns home and denies taking it, which leads to Grace and Val going fisticuffs again. Grace admits that she had fun with Val and didn’t want to admit that she had stole from her. They ends up hugging it out, and Grace steals her watch… which turns out to be Will’s. Meanwhile Jack meets a guy named Bill (Neil Patrick Harris) whom he is crazy about, but Karen points out that he heads up an organization called Welcome Back Home, a group that promotes making gay people straight. Jack and Karen attends one of the meetings, and Jack pretends to be straight and married to Karen. While watching football, Jack tries to subtly hit on Bill, who gets angry and denounces anyone in the club who is using as a place to pick up same-sex members. Consequently everyone leaves, and Bill agrees to a ‘heterosexual soap down’. Marianne Muellerleile is Jodie, and Loren Freeman is Kevin. 12/12/16

• 043. There But for the Grace of Grace – 5/9/2000
  • Will and Grace find out that one of their old college teachers, Professor Joseph Dudley (Orson Bean) is retiring with heart problems. Inspired by the book Tuesdays with Morrie, they decide to go visit the openly gay Dudley. After having an argument on the way there, the arrive to find him an embittered old man, who constantly bickers with his best friend Sharon (Piper Laurie). Will and Grace see themselves in the pair of friends, and inspired by Dudley’s refusal to apologize to Sharon, Will apologizes for everything he’s ever done to Grace. Meanwhile Jack and Karen visit Will’s apartment so that he can give her cooking lessons. Interrupted by a visit from Ben, Jack becomes competitive when Ben proves to be a better chef. Jack maintains he can tap dance better than Ben, and Ben concedes to the depressed Jack… but put on a rousing performance on Will’s freshly treated floors when Jack leaves the room. 3/22/17

• 044. My Best Friend’s Tush – 5/16/2000
  • Initially Will blow’s off Jack’s plea to borrow $50,000 to market his invention The Subway Tush, but then gathers a group of his colleagues to see if they might want to invest. Jack embarrasses Will with his flamboyant presentation, but it turns out that the investors led by Bob (Ken Lerner) want Jack to fire the the under-enthused Will. Meanwhile Karen gets Grace an appointment to pitch her fashion ideas to Robert Lilienfield (Doug Ballard), but Grace decides to give up when she spots snooty designer Helena Barnes (Joan Collins) getting ready to pitch to him as well. Karen has had a long-time rivalry with Helena and takes Grace to Taco Time to see Helena making a pig of herself with the tacos, hoping this will gave Grace the courage to compete with her. Will is hurt when Jack ousts him for the project, but when he finds out that Jack plans to resign from it, he goes to stop him… only to find that he has actually stolen the idea and was getting fired anyway. Grace and Helena both get a meeting with Lilienfield, but before the meeting even begins, Grace begins ranting about Helena’s taco consumption. Regardless she blows the interview because she forgets to bring her fashion book… but cheers herself up at Taco Time. Rob Britt is Larry. 3/24/17
• 045 & 046. Ben? Her? – 5/23/2000
  • Will and Grace take a magazine quiz to see how fulfilled their life is, and while Grace’s life seems pretty empty, Will, especially now that he has a new boyfriend named Alex, looks fabulous. Will is disappointed that Grace won’t come to his office because she hates his boss Ben. Will arranges for them all to have a dinner together, but is then surprised when after a rocky start, they get along so well that they end up sleeping together. Meanwhile Karen and Jack speculate why Rosario has seemed so out of sorts and it’s because she has fallen in love with the gardener Frank (Richard Gross) and they want to get married. Jack fears what impact this will cause in his life, and demands that Karen give him a half million dollars. Grace and Ben dancing on a tabletop in their office makes Will a little sick… but even more so when Will later finds Ben dancing with another woman. Will thinks Ben’s behavior is inappropriate and puts him in the middle, and Ben forbids Will from representing Jack against Karen. Jack moves out of Karen’s apartment and into Will’s. Will finds out that Grace is still dating Josh, and realizes that it isn’t a big deal to Grace that Ben is seeing someone else… and that he has quit for virtually no reason. When Alex breaks it off with Will since he’s so occupied with everyone else’s lives, Will revisits the magazine quiz and finds that he’s lost everything. He decides to pick up and move to a tropical island to get away from everything, but Ben tracks him down and asks him to take on a local client for him. Will agrees to do it if he is made partner, but when he goes to visit the client, he finds that it is Karen, who is living there with Stan and Rosario. Pablo Cartaya is Jack’s boyfriend Fernando. Gordy Owens is Karen’s servant. Michael Edward Thomas is the Caribbean houseboy. NOTE: This is a one-hour episode that airs as two episodes in syndication. 10/4/17

SEASON 3

• 047. New Will City – 10/12/2000
  • Tired of Karen’s abuse and Stan’s continual high-cut robes for the past three months, Will decides to leave the island and return home. Karen soon follows and tricks Rosario into smuggling some black pearls through airport security, which lands Rosario in jail in Queens. Will is surprised to see how close Jack and Grace have become, and especially that Grace prefers Jack’s advice to stay with Ben over Will’s advice to go with Josh. Will gets cranky over this, so Grace finally confronts him and tells Will that her love for him is like a scar, kind of ugly but always present. Jack shows up and insists that Grace dump Josh, and admits that he only chose Josh because he had some special quality… namely that he is gay and made out with Jack. Karen feels guilty about Rosario and begins having guilt pains in her stomach, so she finally goes and retrieves her from jail. Timothy Davis-Reed is the customs officer. Steve Shroeder is the delivery boy. 5/14/18
• 048. Fear and Clothing – 10/19/2000
  • When Grace hears an intruder trying to break into her apartment, she becomes scared to stay in her place so Will lets her come stay with him. Immediately the combination of Grace, Jack, Jack’s boyfriend Mipanko (Derek Basco), and his ‘poppy’, begin to get on Will’s nerves so he gives them an ultimatum that one of them must leave. Grace eventually decides to let Jack stay, but Will admits this is not the decision he was hoping for. As a solution, Will suggests that Jack sublet Grace’s apartment and she can live with him. Meanwhile Karen and Jack run into each other for the first time since their falling out, and refuse to speak to each other. Will intervenes and tells Karen to just accept Jack for the way he is. Karen tries this, but Jack wants nothing to do with her… until they see Grace slip and bond again while making fun of her. 5/15/18
• 049. Husbands and Trophy Wives – 10/19/2000
  • Will’s old friends Joe (Jerry Levine) and Larry (Tim Bagley) invite Jack and Will to visit them at their home in the South Hamptons, and they are excited to accept the invitation, envisioning a weekend of debauchery like they had had in the past. However upon arrival they find that the guys have adopted a baby named Hanna, and the other male couples all have babies as well. Prepared for a much more subdued weekend now anyway, Will volunteers to babysit Hanna so that Joe and Larry can get away to see a movie. Will’s fatherly instincts kick in for a while… until the baby starts to cry. This leads to him bickering with Jack, who tells Will that he’s just angry because he will be a lousy father. This depresses Will as they head home, but Jack cheers him telling him he’s been a spectacular father figure to him. Meanwhile Grace attends a yacht club party with Ben, where Karen and Stan attend as well. It becomes clear that Karen is jealous of the attention that Grace is getting from Ben. Grace thinks it is nice to finally be able to rub Karen’s nose in something, but Rosario tips off Grace that Karen is already upset because she is close to the age of the last woman that Stan dumped. Grace then convinces Ben to flirt with Karen. This not only cheers up Karen, but makes her even happier when Stan spots them and has a man (Christopher Randolph) kick Ben out the club. Yvans Jourdain is Jon. 12/26/18
• 050. Girl Trouble – 10/26/2000
  • Will works on a gay sensitivity seminar for the local police precinct, but Grace suggests that he and Jack put on a skit instead. He also enlists the help of two lesbians named Terry (Megan Cavanagh) and Annie (Henriette Mantel), whom Jack mercilessly insults at every opportunity. As the ladies are nearing the point of walking out, Will convinces Jack to take it as an acting challenge to treat the women with dignity, a challenge Jack quickly rises to. However when Will get annoyed by the character just before the presentation and tells Jack to drop it, Jack immediately returns to the insults prompting Terry and Annie to walk out. This leads to a war of words and a physical altercation between Will and Jack, which the police officers mistake for the presentation. Officer Kirk Cox (Christopher Darga) indicates that they adeptly showed how words can hurt, while Officer Bob (Louis Giovanetti) hints that he himself is gay. Meanwhile Grace works with an intern named Gillian (Natasha Lyonne) who is enamored with Grace’s work. However when she meets Karen, she seems even more impressed with her, and soon Karen has molded her into a virtual clone who takes delight in insulting Grace. However she goes a little too far for Karen’s taste, and Karen sings Grace’s praises and encourages her to return to being Grace’s intern, mixing in a few insults for Grace as well. 12/26/18
• 051. Grace 0, Jack 2000 – 11/2/2000
  • Will confides in Jack about a new love interest, a souvlaki vendor he met on the street who doesn’t speak English. Later when Jack introduces his new nightclub act Jack 2000, which includes a duet with himself on screen singing Hush Little Baby, and it begins to bomb miserably and Jack faces a heckler (Jeremy Forte), Jack resorts to poking fun of Will’s new relationship and his failed relationships in general. Will is livid and vows never to tell Jack another secret, even when Jack spies two male twins leaving Will’s apartment. Jack is so upset by this, that he can barely muster any energy at all during his next show. Karen comes to get Will and tell him how upset Jack is, so Will gives Jack permission to use him for amusement in his act. However when the time comes, Jack can only introduce Will as his friend. Meanwhile Grace decides to break it off with Ben, but Ben refuses to listen and insists that they aren’t broken up. Grace tries to visit Ben to make sure she is clear, but they only end up sleeping together again… three times. Finally Karen convinces Grace that she is much happier with Ben, so she decides to continue with the relationship. However by then, Ben has lost interest and doesn’t see a future with her. Although she tries the same tactic, Ben is able to successfully end the relationship. Troy Norton and Wil Bowers are audience members. 12/26/19
• 052. Love Plus One – 11/9/2000
  • Grace’s ex-boyfriend Nicholas (Jeremy Piven), with whom their relationship thrived on bickering and then making up, comes back in to town and asks Grace to see him. She is hoping for a fling, but after starting a quick fight and then kissing him passionately, find that he has his girlfriend Paula (Maria Pitillo) with him, and then finds out that they want to have a threeway. Grace won’t consider it, until both Karen and Will make fun of what a prude she is, so she agrees to go forward with it. Meanwhile, Jack starts work at Banana Republic and develops a crush on a customer named Matthew (Patrick Dempsey), but feels that he is too intelligent for him to flirt with. He gets Will to feed him his conversational dialogue through a microphone headset, but it quickly gets too complicated when Jack isn’t interested in any of the topics. However, Matthew figures out the ruse, and asks Will to call him instead. Grace shows up dressed in multi-layers for the threesome, which is quickly interrupted when Nicholas and Paula get into an argument. Grace who is timid, yells at them and tells how she had to shed her prudish nature to be there, and demands that they get it on immediately. This excited Nicholas and Paula, who descend on her, but then she quickly realizes she isn’t ready after all and backs out. She admits her failure to Will, but tells Karen that she enjoyed the whole threesome experience. Karen, despite her initial titillation, then feigns disgust by the whole affair. Will Hall and Hope Shapiro are customers. Eric Roth is a salesman. 12/26/19
• 053. Gypsies, Tramps & Weed – 11/16/2000
  • Will is celebrating his birthday with Jack and Grace at a restaurant, and Grace is irritated with the watier Lenny’s (Robert Romanus) poor service. Karen shows up, but leaves quickly when she sees better company in the restaurant. Jack gives Will a Cher doll, which Will immediately gives back to him… as Jack intended. Grace gives him a gift certificate for a psychic reading with Psychic Sue (Camryn Manheim). Before they leave Grace complains to the manager (Adam Lazarre-White), and gets Lenny fired. Naturally she can’t forgive herself and hires him to work as an office boy at her place. Soon however he begins selling pot in the office, so she is forced to fire him again. Karen naturally wants him back when she sees what he has to peddle. Will attends the psychic reading half-heartedly, but when she correctly predicts that Grace will trip and break China, and that Will will receive a dog collar from his childhood beloved dog, he runs back to Sue to learn more about his love life. However when she tells him that the man he will spend the rest of his life with is Jack, he begins to worry. He also makes it clear to Jack that he will never have sex with him. They agree to a number of stipulations if they ever did wind up spending their lives together… and it looks very much like their current relationship. Everyone gets annoyed with Jack treating the Cher doll like a real person… including Cher (herself) herself, who he runs into at a restaurant. However Jack thinks she is a drag queen posing as Cher even after they both do their best ‘impressions’ of her. Kenneth Alan Williams is Lenny’s client Steve. Steven Christopher Clark and Rochelle Hannah are other stoners. Keith Allan is the photographer. David Vallaincourt is the student. 4/9/20
• 054 & 055. Lows in the Mid-Eighties – 11/23/2000
  • While waiting for a table at a restaurant, the four friends meet a girl named Pam (Ever Carradine) who is upset about her boyfriend who is obviously gay. Jack drags her over to the group and tells them the story of the early days of Will and Grace so that the same fate doesn’t befall her. They flashback to 1985 when Will and Grace are at a keg party as dates, and although Will tells his friend Rob that he is having sex with Grace, she confesses to Ellen that they haven’t and that Will is more interested in doing her hair. Also at the party is high schooler Jack who tries to convince Will that he is in fact gay, and guesses correctly that Will makes excuses every time Grace wants to have sex. Later they go to celebrate Thanksgiving with Grace’s mother Bobbi, her gay pianist Julius (Neil Vipond), and Grace’s snotty sister Joyce (Sara Rue), who has a crush on Will. Bobbi tells Will and Grace that they have to sleep in separate rooms, which bothers Grace but doesn’t bother Will one bit. When Grace sneaks in the room to sleep with Will, he avoids her and calls Jack to tell him that he is not in fact gay. Angrily he returns to Grace, but can only summon interest in Grace by staring at a poster of Kevin Bacon. He tells Grace they shouldn’t sleep together because he loves her and wants to wait until they’re married. Grace says yes to his proposal, and runs to tell her family. As they celebrate, Will drags her off to tell her that he’s gay. She is furious and devastated, and after telling everyone, she throws him out. They don’t speak for a year, while Will tells his friends and family.  The next year at Thanksgiving, Jack tells Will that he is in love with him, but Will says he thinks of Jack more like a beloved pet, after which Jack tearfully tells him he was only testing him. Will runs into Grace at the market and they make up and becomes friend again. Karen’s story flashes back to when she was dancing with the Sultan of Bohran (Richard Assad), and turns down the proposal of a man named Clayton (Raymond Forchion) and tennis player Martina Navratilova (herself) because she is in love with Stanley Walker…none of which has anything to do with the subject at hand. When she finds out that Stanley is married, she whines about it to the bartender, but is interrupted by the cigarette girl who tells her to shut up and puts her in her place. It turns out to be Rosario, and Karen asks her to come work for her and Rosario agrees. Back in the present, Jack reveals that Will slept with a girl named Diane after they broke up, causing Grace to storm out of the restaurant. Will chases her down in the rain and tells her that he needed to try it with someone that he didn’t love. Michael D. Trail is Guy. Scott Berman is Dontonio. NOTE: This is a one-hour episode that airs as two episodes in syndication. 4/9/20
• 056. Three’s a Crowd, Six Is a Freak Show – 12/14/2000
  • Will and Grace each have had great first dates with guys named Paul (Paul Fitzgerald) and Mark (Ken Marino), but both relationships are threatened when Grace gets a freckle removed that causes a huge sore on her lip, and Will realizes that Paul has asked both him and Jack for dates separately. When Grace joins Karen in the toy store where she is picking out a gift for her stepson, Grace sees Mark in the store and attempts to hide form him in the kids ball pit. She winds up coming clean and showing him the sore. Mark says he’s perfectly find with it, especially considering the fact that he has six toes. This is too much for Grace to handle and she breaks it off with Mark. When Will points out how shallow Grace is being, she agrees to see him again. Will and Jack agree to both back off seeing Paul, as hard as it is for both. When Paul keeps calling Will, he gives in and goes out with him again. When Will admits this to Jack, he is furious and accuses Will of not caring about his feelings. On their second date, Grace tries to not think about it, but when Mark takes off his shoes and ask her to rub his feet, she can barely hide her disgust. She uses the excuse that he’s not a Celtics fan to throw him out, admitting that she is in fact shallow. Will has a great date with Paul, but ultimately tells him that he can’t see him anymore. After they end the date, Will goes to tell Jack the news and finds Paul in his apartment. Will and Grace agree not to talk about future prospects anymore out of fear of jinxing the relationships. Bob Rumnock is Phillip, the toy store salesman. 7/21/20 
• 057. Coffee & Commitment – 1/4/2001
  • With their friends Larry and Joe getting married through civil union, they go out to eat with Will and Grace and ask them to do a reading together at the wedding. Will becomes visibly irritated when he is not only asked earlier in the day to cover Grace’s dry cleaning, but also to pay for the entire check at dinner. He buys a $400 kayak as a wedding present for the guys, but refuses to allow Grace to sign the car. She is taken aback and comes up with her own gift: a ceramic hand print she made in camp as a child. Meanwhile Jack has been drinking an inordinate amount of coffee because he has a crush on a barista, and soon finds he is addicted. Karen agrees to give up coffee as well in order to help Jack get off it. They all ride together to the wedding as Jack is suffering from withdrawal, and Will and Grace are bickering over money the entire time. When they arrive at the wedding, Will makes it clear why he is so upset with the situation: he does not want a ‘wife’. Jack and Karen are informed by the waiter (Jeffrey Patrick Dean) that the wedding is dry, and they are only serving coffee. After listening to brief toasts from an out-of-his mind Jack, and Joe’s embittered sister Jean (Lori Alan), Will and Grace do their reading. Will is so touched by it that he apologizes to Grace and they profess their love to each other, nearly walking out of the ceremony as if they had gotten married. Will allows her to add her name to the kayak gift. Jack makes it through the proceedings without coffee, vowing that he will never allow a crush to force him into bad habits, but when a cute guy (Jimmy Shaw) offers him a cigarette, he jumps at the chance to smoke with him. Butch Klein is the guest who makes fun of Grace’s gift. Wanda-Lee Evans is the Justice of the Peace. 7/21/20
• 058. Swimming Pools… Movie Stars – 1/11/2001
  • While browsing the newspaper apartment listings, Will and Grace find that actress Sandra Bernhard (herself) has hers listed. They decide to pretend they are interested buyers in order to see the place. Meanwhile Jack defeats fellow archrival eBay buyer Dr. Dangerous in winning a scooter signed by Ricky Martin, and in to ensure that he he can always defeat them, he gets an online beeper that lets him know when he’s being outbid. The realtor Joan (Pamala Tyson) lets Will and Grace check out Sandra Bernhard’s apartment, and while they are snooping, Sandra comes home. They hit it off with her and managed to get invited back to a party she is having that night so they can check out the nighttime view. They become even better friends, and Will spends a good portion of the evening chatting with her. At some point, he is forced to make an offer for a million dollars, which is roughly half of the apartment’s value, thinking it would never be accepted. However, she has taken such a liking to them that she does in fact accept it. They go over to her place to tell her that they only wanted to meet her, and they wind up joining her and her piano player Mitchie (Mitch Kaplan) singing Midnight Train to Georgia. Sandra is impressed and invites Grace to join her onstage. Grace is too excited to tell her the truth, but once they feel comfortable with her, they finally admit they had no intention of buying the place. Sandra Bernhard delivers a profanity-laden tirade about how much of time of hers they wasted. Karen is irritated when Mason makes the swim team at school, but when she shows up late for one of his swim meets, another mother named Cheryl Bricker-Fossberg (Cheryl White) tells her how horrible of a person she is, a notion that Jack seems to second. Karen makes up for it by giving Mason a pep talk after the meet, but Jack informs her that she was speaking to the wrong kid. Jack runs into a little girl (Shandra Olds-Whitlow) who he comes to realize is Dr. Dangerous, and she has the same online beeper that he is using. Will and Grace vow never to try anything like they did ever again, but soon a realtor (Molly Bryant) across the hall is getting ready to show the apartment of Uma Thurman and Ethan Hawke, so they jump on it. Thi Nguyen is Karen’s manicurist Mei-Lihn. Susie Geiser is the mom at the meet. 11/5/20
• 059. Crazy in Love – 2/1/2001
  • After another party at Jack’s at which Will met no one he liked, Grace suggests he call a guy named Matthew Moshea (Patrick Dempsey) whose card he’s been carrying with him. Will is resistant because he is a sportswriter, but Grace uses reverse psychology to get him to call. When Will finds out that Matthew’s ex-boyfriend wasn’t into sports, Will works overtime to try and pretend he is, even spending eight hours in the batting cages under Grace’s tutelage. After Matthew gets a broadcasting promotion, Will suggests they celebrate in the cages, but Matthew asks him to play basketball instead. When Will has to pay off a child (Murphy Dylan Devine), it becomes obvious that Will isn’t athletic. Matthew doesn’t mind but does ask that Will is more honest with him. Meanwhile, Grace agrees to decorate Jack’s apartment… but only if Karen pays her double her normal rate. Jack’s impossible requests nearly drive Grace crazy, and it doesn’t help when Karen continually balks at the price tag. When she leaves behind her planner, Jack and Karen find a doctor’s note that Grace had written herself to get out of jury duty, indicating that Grace has a borderline personality disorder. Believing it to be true and intensified even more when they hear Grace screaming at the neighbor Mr. Zamir, they start to walk on eggshells around her, acting as if they are scared to death. Grace sees the fake doctor’s note and realizes what is going on but continues to play up her craziness so they will let her finish the apartment in peace. After it is all over and Karen has paid her, she admits that she was faking and tells them the real reason for the letter. They do not believe her, and she continues to look crazy to them as she angrily swats a fly that has been following her. 2/24/21
• 060. Brothers, a Love Story – 2/8/2001
  • As Will tries to acclimate himself more to sports, he is proud to watch Matthew delivery a newscast from the locker room… until he meets the station manager Harry Zalen (Dion Anderson) and Matthew introduces Will as his brother. Will is furious, and Grace is likewise furious and tells Will he should break it off with him if he can’t be himself. Will does in fact confront Matthew, but ultimately likes him too much to dump him, so he goes along with trying to be discreet by taking him to a fish restaurant in Queens that Jack recommends where closeted gays often go. Grace remains furious and gives him the silent treatment but goes to the restaurant to get the blooming onion. Meanwhile, Karen is trying to find Christmas gifts long after the fact, since she hasn’t consulted her calendar in months. To pass the time, she and Jack go to her safety deposit box to try on her jewelry. While there, Karen finds Stan’s latest will that donates a third of his money to charities. Karen blames Will for talking him into it as his lawyer. While Will and Matthew dine at the restaurant, Grace waits for her onion and shoots daggers at them. Will continues to play along until Mr. Zalen shows up and starts talking about rumors that he heard that Matthew is gay. Matthew continues to deny it, but Will can no longer hold his tongue and admits to his ‘brother’ that he is in fact gay. Matthew discreetly tells Will that he can’t reveal himself to his boss. While Will is proclaiming his homosexuality, Karen shows up yelling at him, but her choice of words makes her sound like a jilted lover. Jack also shows up at the restaurant with his lover Justin (George Stults), who happens to be Mr. Zalen’s son. Grace finally gets her blooming onion, and she and Will leave the restaurant. Dennis Satterfield is the cook. Matt Bellner is the towel boy. 2/24/21
• 061. My Uncle the Car – 2/15/2001
  • Will criticizes Grace for keeping her late Uncle Jerry’s Chevy Citation in a storage unit, even though he’s been dead for four years. She claims it is all she has to remember him by, so she decides to take it for a drive. When it barely smarts, and then fills the garage with smoke, Will finally gets her to agree to let him sell it. He gets $400 for it from a nun named Sister Louise (Ellen DeGeneres), but when she finds a tape in the car with a message from Jerry asking her to always remember him by the car, she decides she wants it back. They visit the embittered nun, but she wants $3000 for it, claiming that she needs to deliver her cheesecakes that she is selling as a side hustle. Meanwhile Karen plays pool with her friend, the effeminate socialite Beverley Leslie (Leslie Jordan), but Karen gets suspicious when Rosario knows his drink order by heart, even though he recently changed it. She figures out that Rosario has been cleaning for him and becomes furiously jealous. They decide to play a game of pool for Rosario, and Karen loses, despite her efforts to cheat. When Rosario finds out, she gets angry and quits them both. Jack gets a letter from his mother telling him that his father was a ‘black boy’, so he starts to think he’s African American, even believing that he was overlooked for a cab because of his color. Eventually he finds out that his real father’s last name was Black. Karen confesses to Jack that she doesn’t know how she will get along without Rosario, but she soon returns to her on her own. Will feels bad about the car so he strikes up a deal with Sister Louise that she’ll return the car if they take her on her cheesecake runs. 6/21/21
• 062 & 063. Cheaters – 2/22/2001
  • Will’s father George comes to town for a visit, but after rushing through game night, he takes off early from Will’s apartment and says he wants to relax in his hotel. The next day, Jack is conducting auditions at Grace’s office, pretending that he is putting on a show. Karen is aghast but is quick to jump in and put the wannabe actors through their hoops. They finally take a break so Karen can meet Stan for lunch, but Rosario tells Karen she has no idea where Stan is but has cancelled the lunch date. That night Grace goes on a date with a guy named Ian (Joel McHale) to see Seussical, and they run into George, who is there with another woman named Tina (Lesley Ann Warren). Grace tries to pry it out of George how they know each other, but she only learns that they are ‘colleagues’. When she tells Ian how horrible it is that there’s nothing worse than married men having affairs… so Ian quickly leaves. Grace then asks Karen for advice on whether she should talk about the affair or not – but Karen thinks she is talking about her husband Stan having an affair. She takes Jack and they go to try and follow Stan. Grace decides to tell Will anyway, while Will is preparing dinner for his father. Will blows it off and says he knows about Tina, and that they are merely colleagues. He goes on to admit that he would rather remain oblivious, after all the chaos he caused when he announced that he was gay. Will also insists that they are merely colleagues. Sure enough, George stops by and says he has to cancel dinner, but then Tina comes up to use the restroom. Will says he’s so convinced it is no big deal, that he invites them both to stay for dinner. They spend the entire dinner talking small talk about the weather, until Grace can no longer stand it and has a meltdown and storms out into the hall, followed by Tina. George then tells Will that he is disappointed that Will didn’t drag the situation out into the open. So, Will tells his father that he needs to admit what he’s been doing to Will’s mother, and George agree. Karen and Jack, after a night of following Stan around but only finding him visiting a podiatrist, come to see Grace and Karen demands to know who ‘he’s’ having an affair with, so Grace introduces her to Tina. Karen reads her the riot act about breaking up a marriage and happy home, but then Grace tells Karen who she’s really having an affair with, and Karen can offer nothing but congratulations. Dirk Shafer is auditioning actor Blaze. Christopher DeLisle is Elias Page, second auditioning actor – billed as Dan in the credits. David Costablie is the man in the restaurant. Sara Van Horn is the woman in the restaurant. NOTE: This episode originally aired as one forty-minute episode, then was divided into two syndicated episodes. The second part introduced a recap from the first part, as well as adding additional scenes that did not appear on the DVD version. These include Karen and Jack tracking Stan to Burger King, where he orders a salad. This, combined with the visit to the podiatrist, convinces them that Stan is having an affair. Jack gets Karen a ‘richest men in America’ magazine, so she can start shopping for her next husband. She then realizes she still loves Stan, so she returns home, where Rosario tells her that Stan has been doing all of this for Karen since he’s afraid she finds him disgusting. Karen rejoices that Stan is upstairs waiting for her but decides to go out on the town with Jack. Rosario berates her for this, but when Karen invites her to come, she becomes fine with it. Back at Will’s apartment, he tells Grace that she was way out of line for interfering… but that he owes her one. 11/13/21
• 064. Mad Dogs and Average Men – 3/15/2001
  • Will wants to break it off with his latest needy boyfriend Paul Budnik (Peter Jacobson), but he is having trouble because he is so attached to Paul’s dog Pepper. Meanwhile Grace meets Karen’s nephew Sumner Davis (Paul Satterfield), but Karen warns him not to date him because he is married. Grace later finds out that he is indeed single, so Karen admits that he is actually a womanizer who takes women for their money. She then finds out that this isn’t true either, so she tracks Karen down at the opera to corner her into the truth. After several more ridiculous lies, she finally admits that Grace is too good for him. Will finally decides to break it off with Paul, but when Paul tells him that he’s going out of town and asks him to watch Pepper, Will jumps at the chance. Will goes all out to prepare a special meal for Pepper of sautéed dog food while Jack takes him for a walk. Unfortunately, Jack comes home with the wrong dog, having lost Pepper while playing fetch. Jack suggests that Will tells Paul that it was Will who lost him so that he will break it off with Will. However, it has the opposite effect, and Paul becomes more needy than ever. After Will reluctantly agrees to take Paul on a trip for the weekend, Will finds out that Paul had Pepper all along, and just uses him to get men. Bill Idelson and Seemah Wilder are Ben and Lois, the old people in Karen’s opera box. Ellen Idelson is the usherette. 6/21/21
• 065. Poker? I Don’t Even Like Her – 3/29/2001
  • Will and Grace have regular poker games with their friends Rob, Larry, and Joe, but Grace’s obnoxious behavior and annoying betting style not only leaves her in debt to the guys, but also forces them all to ask Will to exclude Grace from further games. On the night of their next game, Will tells Grace that they want her to bow out just before they arrive. Grace pleads with them to give her another chance, and she guarantees that she is now a better player. Sure enough, she starts getting winning hands and taking the guys for all of their money. When everyone leaves the room for a break, Grace admits to Will that she has been cheating the entire time. Will is furious and wants to tell the guys, but Grace tells him the story about how she needs to get her grandmother’s jewelry back that she had previously lost to the guys. She claims it was given to her grandmother by her best friend Ruth. However, during the game, it comes to light that Grace had actually bought it from a trans-woman who dressed like June Carter Cash. Will is even more furious but goes on with the game and wins a large hand with a bluff to Rob. He then accuses Will of cheating, and the two of them nearly comes to blows. In order to stop the fight, Grace admits that it was her who was cheating and promises never to play with them again. Will and Rob then congratulate each other for their fake performances designed to get Grace to admit her cheating. Meanwhile, Karen wants to get a shoulder plastic surgery procedure but wants to see it on someone else first. Jack poses as a massage therapist and tells Karen’s socialite ‘frenemy’ Candy Pruitt (Christine Ebersole) that it is the ‘Year of the Shoulder’ and pretends that Candy has almost no shoulders. Due to some ambiguous information, Karen thinks that Candy died during the procedure and feels terrible, but then sees Candy, fresh back from her surgery. Candy tells Karen that she received the last pair of shoulders and then rubs it in to Karen that she will have to live with ‘last year’s shoulders’. 4/26/22 
• 066. An Old-Fashioned Piano Party – 4/19/2001
  • Grace runs into her old friend Heidi Dauro (Gigi Rice) and find out that Heidi’s gay best friend Charlie has moved to San Francisco to be with the love of his life, causing Heidi and Charlie to eventually drift apart. Grace is aghast when she thinks that this could ultimately be her fate with Will, and Will seems to think that him moving away was predictable since there was ‘nothing’ keeping him in New York. Grace’s idea is that she and Will go in on something expensive together, presumably because it would make it harder for them to separate, so she buys a piano using both of their money. She then forces Will to stay home night after night learning to play, while she sings along. Eventually Will gets antsy and wants to go out with friends, while she tries to keep him home. Will comes home one night ready to go out, only to find out that she has invited Jack, Karen, Larry, and Mr. Zamir over for an old-fashioned piano party. When Will finally blows his stack, Grace breaks down and admits that she is fearful that they will drift apart. Will’s only recourse is to play the piano and sing Love Will Keep Us Together to her. Meanwhile, Jack goes through a breakup with his two-day boyfriend Rocco (Philipp Karner), causing him to bury himself in his writing of erotic fantasy involving Rocco. Karen gets incredibly aroused by reading his fiction and is so addicted to it that when Jack and Rocco get back together, she pays Rocco $50 to break it off with Jack so that he will return to his writing. Jack is furious and hurt by what she did, but gleefully accepts $200 from her to continue the writing. Jovial Kemp and Doug Devine are the piano movers. 4/27/22
• 067. The Young and the Tactless – 4/26/2001
  • Will is excited that a hip spot called the Atom Bar is re-opening, but Jack thinks it is a waste of time for Will to attend since he just stands in the corner alone at clubs like that. Meanwhile, Karen laments that her mother-in-law Sylvia (Ellen Albertini Dow) is in town. She brings her over to Will’s house and then abandons her there, so Will and Jack are forced to take her to the Atom Bar. Grace find out from Mr. Zamir that a new tenant in 12C has taken her wet clothes out of the dryer in order to put his in. Grace goes to see this guy named Nathan (Woody Harrelson) and read him the riot act, but he only ends up getting under her skin further when he says he can’t talk because he’s making a mix tape in order to get his girlfriend Vicki back. Then he makes fun of her for giving him relationship advice while she lives with a gay man. At the Atom Bar, Jack runs wild and hooks up with pairs of men, while Will stands alone with Sylvia and laments his loneliness. She gives him advice that nothing will change unless he does. This gives Will the kick in the pants to accept a date with a young 24-year-old named Scott (Branden Williams) who works at Will’s video store. Will thanks Sylvia for the encouragement, but when she finds out that Will hooked up with a man, she goes on a tirade of homophobic slurs. Grace keeps returning to Nathan’s apartment to defend herself from his latest insults. Eventually, he summons her back by putting his underwear in her laundry. This time he shows her a romantic setup he created for Vicki to simulate Venice. Soon Grace realizes that he is trying to have a date with her, after having already failed with Vicki. She chastises him for even considering this, but when he plants a huge kiss on her, she agrees to one date. Will and Jack wheel a drunken Sylvia back to Karen’s on a dolly. 8/27/22
• 068. Alice Doesn’t Lisp Here Anymore – 5/3/2001
  • Grace learns from the monthly family newsletter from her mother than an old schoolmate named Alice Robinson (Alex Kapp Horner) has died. Grace feels terrible because she used to make fun of her because of her speech impediment. In fact, it was Grace who gave her the nickname “Mrs. Lazyface.” Grace then feels compelled to attend her funeral to make her apologies, and she talks Will into going along. Meanwhile, Jack finds out that his one-man show Jack 2001 for a MAC award. Jack decides that it would appear cooler if he sent in his acceptance speech on video, supposedly from the set of his next exotic movie. He chooses to film the video in Will’s kitchen. When Karen runs back to Jack’s apartment for champagne, she overhears a message from Ted from the MAC awards saying that there was a mistake and Jack 2001 was not nominated. At the funeral, while Will is more interested in hitting on Alice’s older brother Gabe (Todd Stashwick), Grace finds out that the deceased Alice was really Alice’s grandmother with the same name. Grace then attempts to make an apology directly to Alice, but Alice is unwilling to forgive and calls her a bitch. When the minister (Noel Conlon) invites Grace to speak at the funeral, Grace makes a heartfelt apology for her behavior toward Alice and asks for forgiveness. Alice forgives her and introduces her to some of the students with speech impediments she now works with. Unfortunately, Grace has burnt her mother on coffee, and it appears she is making fun of them when she can hardly speak. Jack realizes while filming his acceptance speech that acting is important enough to him that he should be there to make the speech in person. Karen is then forced to tell him that he wasn’t nominated after all. Karen says she would have given him a boy, jewelry, or money, but then realizes that acting is its own reward. Then she says she was only teasing, and brings in a man (Christian Middelthon), with a tiara and handful of cash. Will finally makes his move with Gabe, only to be shot down and berated for hitting on him at his grandmother’s funeral. Patricia Place is Myrtle. NOTE: David Doty is credited as Harry, but his part appears to be cut from episode. 8/27/22
• 069. Last of the Really Odd Lovers – 5/10/2001
  • Will is embarrassed because he’s been dating a 23-year-old clerk from the video store named Scott Sender (Branden Williams) since he is so young. Grace likewise has been going out with Nathan, who acts immature and strange on their dates, and then tries to get her to go to bed with him at the end of the date. Neither Will nor Grace will tell the other who they are going out with. Meanwhile, Val comes and tries to collect spare cans of food from Jack, even though it is clearly for her. She invites Jack to come up for dinner to eat some of the canned goods, but Jack tells her that he’s getting ready to his show Jack 2001. Will has an encounter with Nathan on the elevator, and Nathan winds up sneezing on Jack’s neck. When he gets home, he and Grace want to tell each other who their dates are, but Grace decides not to mention it when Will goes off about Nathan. Will also is secretive about Scott. Jack performs multiple shows of his play, and although Karen only stays for one of them, Val stays for all of them, causing concern for Jack that she is stalking him. On her way home, Karen spots Will out with Scott and can’t help but stare and laugh. Grace keeps trying to push Nathan away and stop seeing him, but he keeps charming her, and she keeps going back for more. Karen and Jack wind up on the elevator at the same, and Grace is petrified he will tell Karen… and he inadvertently does. Jack wakes up and finds Val in his bed, so he kicks her out and threatens to call the police. When Grace finds out that Karen is on her way over to visit, she preemptively tells Will that she is dating Nathan. However, instead of reciprocating, Will tells her that it hurts that she’s been lying to him. Grace agrees to do most of the chores to make up for it. Karen drops by to deliver a ‘big surprise’, which turns out to be that Karen bought a ring that Grace had really wanted. She also mentions that Will has been seeing Scott. The tables are then turned, with Will taking over the chores. They finally sit down and decide that if they feel they have to keep Scott and Nathan from each other, then they are probably the wrong guys for them. The mutually agree to break it off with their partners. Will does it with no problem, and Grace does it too… but then makes out with Nathan. Jack has been suffering withdrawal from Val not being at his show anymore and begs her to come back. Adam Barr is the guy obsessed with Jack’s autograph on Val’s breast. 12/12/22
• 070 & 071. Sons and Lovers – 5/17/2001
  • As Will keeps an eye on a guy named Chris (Michael Philip), whom he refers to as his ‘imaginary boyfriend’, in the coffee shop, Jack sends a letter to the eleven Black brothers of New Canaan, Connecticut, one of which Jack thinks is his father. Karen spills the beans to Will that Grace is still seeing Nathan, who Will thinks is beneath her. Grace goes on about how much she really likes him, and Will tells her to do what she wants but to keep him away from him. Jack gets a letter back from a Joe Black, telling him that he wants to meet with him. Karen offers to throw them a party but wants to hold it at Will and Grace’s. While Grace and Nathan are being intimate, Grace realizes that Nathan’s ex-girlfriend Vicky (Helen Eigenberg) is still living with Nathan when Vicky walks in on them when they are being intimate in bed. Grace decides to move Nathan into her and Will’s apartment, a situation Will is not fond of, and shows by nitpicking everything Nathan does. Later than night, they all host the reunion for Jack, but his father doesn’t show up, but instead Joe’s wife Jo (Claire Malis) shows up and tells them that Jack’s father Joe passed away five years earlier. Jack is inconsolable and retires to Will’s room, where Will tries to comfort him. Nathan joins them with some Jack Daniels and makes a very touching toast that makes Jack feel better. Even Will is impressed, and the three of them drink all night and fall asleep on Will’s bed. From then on, Will and Nathan become best buddies, and they all three start hanging out together. When they all go to a movie together, Grace and Nathan are forced to sit apart from Jack. Nathan is happy about this because he wants to tell her something he’s never said before. Grace gets cold feet because she thinks he is going to say, ‘I love you’, so she rushes to sit next to Grace during the opening commercial. When she returns, Nathan is annoyed and simply clams up. Meanwhile, a boy named Elliot (Michael Angarano) tracks down Jack via Karen, and tells him that his mother, a nurse at a sperm bank, used sperm that Jack had donated. Karen faints when she finds out Jack has a son, but Jack simply chooses to ignore him. Back at the coffee shop, Will continues to contemplate talking to his ‘imaginary boyfriend’. Grace buys two tickets to Morocco and wants to take Will with her. He questions her leaving her blossoming romance for three weeks, but she says he’ll be fine. Karen tries to talk Jack into taking the responsibility of his son, but Jack doesn’t want to be with him. Elliot tells him that he just wanted to meet him, and probably doesn’t understand what it’s like to not have a father. When Jack realizes that Elliot is in the same situation that he was and decides to be a small part of his life and take him out for lunch. On the day of the big Morocco trip, Grace goes to the airport ahead of Will. Nathan shows up at the apartment and tells Will that Grace broke up with him. Will is stunned by the news, and when he arrives at the airport, he questions why Grace broke it off with him. She tells Will that she’s not ready to change her life, and that she enjoys her and Will’s life as it is. Will tells her that she doesn’t want her to use him as an excuse to not get on with her life. He asks her if she loves him, and when she can’t answer, she encourages her to go find out. She gets in the car to head back home, where she finds Nathan waiting. They say ‘I love you’ to each other. Will then bumps into his ‘imaginary boyfriend’ Chris, who is heading to France for a bike tour. Will decides to join him. David Correia is the Sky Cap. John David Conti and Marcia Ann Burrs are the movie theater couple. 12/13/22

SEASON 4

• 072. The Third Wheel Gets the Grace – 9/27/2001
  • Will returns from France from his bike tour, but his relationship with Chris has fizzled out entirely. Will is more attached to the pair of jeans that he bought in Paris, which everyone thinks is a pair of women’s jeans. The next morning, when Nathan gets up, he finds only Jack at the apartment as Grace and Will have gone out to breakfast. Jack tries to annoy him by telling Nathan and Will are like a cutesy couple who finishes each other’s sentences. Nathan maintains that he thinks their friendship is great and he isn’t bothered, but when Grace denies Nathan three dates in a row because she is doing something with Will, he does start to get a bit annoyed. One of the places that Will and Grace were planning to go was the big sale at Barney’s, Nathan tells Grace that he wants to go. Meanwhile, Rosario brings Karen flowers because it is their fifteenth anniversary together. Karen agrees to buy her some new shoes at Barney’s but isn’t planning on going along with her until Rosario demands that she spend time with her after she took care for fifteen years. Jack worries about being a good father to Elliot, so Karen advises him to take him shopping at Barney’s for school clothes. One shopper (Jacqueline Beatty) wants to know where Will got his pants because she wants a pair herself. Several other women (Karen Co, Jessica Margaret Dean, Debra Kay aka Debra K. Beatty) try to bid on them since they all think they are women’s pants… until Will is finally convinced. Nathan quickly folds under the pressure as Grace is over the top as she picks out her wardrobe, asking questions he can’t answer, and has meltdowns when he says that an outfit makes her look fat. Rosario can’t make a decision about what she wants, and finally admits it is because she wants to spend more time with Karen. Jack is disappointed when Elliot doesn’t care for the flashy clothes Jack picked out, but says he said he did originally because he wanted Jack to like him. Jack tells him that as his father, he will always like him. Will finally steps in for Nathan and gives him some relief, and Nathan is thrilled to be off the hook. That night as Will and Grace look through their new purchases, Nathan watches the Three Stooges and waits for Grade to call on him to take her to bed. 5/28/23
• 073. Past and Presents – 10/4/2001
  • Nathan’s birthday is coming up and Grace has bought him a signed first edition of the book Zen and the Art of Motorcycle Maintenance. However, before she can give him the gift, Karen gives him a new Ducati Monster S-4 motorcycle, leading to Nathan doing the happy dance. Grace then gives him the book, which he acknowledges and tosses aside. Grace is so furious with Karen that she threatens to kick her ass. In fact, Karen is forced to bring along a bodyguard the next time she shows up for work. Meanwhile, an old classmate bully named Kevin Wolchek (Adam Goldberg) who used to force Will to do his homework for him, is now working at Will’s office. Will is surprised when Wolchek demands that Will draft a contract for his upcoming meeting with D.T. Peterson (Walter Addison). In order to get out of it, Will decides to stay home sick from work the next day. Jack pep talks him into standing up for himself and not succumbing to this bully again. Grace decides to forgive Karen, but to get him a gift that is better than the one she got for Nathan, so she maxes out her credit cards to get him an expensive diving watch. As Grace and Nathan head to dinner that night, Grace hints around about the watch, but is then devastated when Nathan tells her that he doesn’t like wearing watches. Will stands up to Wolchek and tells him that he will fight him if necessary, but when Wolchek tries to take him up on that, Will quickly backs down and hands over the contract that he asked for. Grace is clearly irritated at dinner with Nathan, and finally admits that she is upset about how much he liked the bike Karen gave him. She tells him that she tried to get him something better but that it failed since he hates watches, and that she has nothing else but the fact that she loves him. This prompts him to do the happy dance in the restaurant and tell her that it is the best gift he’s ever gotten. Wolchak takes the contract to Mr. Peterson and finds that Will has insulted both him and Peterson in the contract draft. As Peterson gets more and more angry as he reads it, Will dances around outside the room until Wolchek finally leaves and chases him. 5/28/23
• 074. Crouching Father, Hidden Husband – 10/11/2001
  • Elliot builds up the courage to ask a girl named Nancy (Landry Allbright) to go to a school dance with him, but she tells him that she is already going with someone else. Jack wants to step in and help him, so he asks Grace if she will go with him. All he has to do is remind her of the boy that stood her up when she was a teen, and she agrees to go. Meanwhile, Karen calls Will to the office for an emergency, but it turns out to just be to un-jam the fax machine. He warns her that he is very busy and has other clients, so even though he works for her as her lawyer, he is not at her beck and call. When they get to the dance, Elliot finds that Nancy’s date has an allergic reaction to a peanut and did not accompany her. Jack tells Grace to go sit with a pair of reject girls (Lauren Schaffel, Sydney Berry), where she bores them with her takes of teenage woe. Jack tries to get Elliot to ask Nancy to dance, but he is afraid he isn’t a good enough dancer to keep up. Jack then tries to teach him some moves, but when a favorite song of Jack’s comes on, Jack pushes Elliot aside and does a solo performance that all of the kids watch. Elliot is humiliated, and Jack feels terrible. Karen calls Jack again and tells him that INS agents are at her house trying to take Rosario awake. After Will talks to the agent on the phone, he heads over to help, but it turns out that Karen had her gardener pose as the agent, and she only wants Will to uncap a bottle of olives. Again, he is furious and promises not to fall for it again. Nancy comes out to talk to Elliot in the hallway about his father and her own gay mother. The two wind up dancing together, while Grace and Jack look on proudly. Jack even agrees to join Grace for a dance. FBI agents Korn (Hep Jamieson) and Pembleton (James Healy, Jr.) show up to question Karen about Stan’s business practices. She calls Will but he won’t speak to her and is certain that Karen is only messing with him again. When the agents show up at Will’s office, he assumes that Karen hired actors, tells them that his name is Agent Poopypants, pulls down his pants, and begins tickling Agent Pembleton. Karen then shows up at his office and shows him the news broadcasts that Stanley Walker is being arrested on charges of tax evasion. With pants down, he tells the agent that they can direct any questions for Karen to him. 5/31/23
• 075. Prison Blues – 10/18/2001
  • Karen, Grace, Will, and Jack all go to prison to visit Stan. Jack tries to make himself attractive, while Grace fears she will be attacked by a prisoner. While checking in with the prison guard (Brent Sexton), reporter Anthony Dukane (James Black) sees Will and starts to question him about his relationship with Stan. After he says that he is Stan’s lawyer, he falls apart on camera and mixes up his worlds and mumbles through the brief interview. Later, while Jack is watching it on video over and over while laughing hysterically, Dukane calls back to see if he can follow up with Will. He doesn’t want to do it, but Jack says he will take him to his workshop which teaches how to overcome his fear of the camera, and Will reluctantly agrees. Meanwhile, Karen doesn’t like being alone in the house so she drops obvious hints to Grace that she wants her to stay over for the night. Even though she won’t ask Grace directly, Grace gets the hint and stays the night. She ends up having one of the best sleeps of her life and starts to really enjoy all of the pampering. The next day when Grace parks herself in Karen’s luxury bathtub, Karen starts hinting around that she wants her to leave. Grace keeps telling her that she knows that Karen needs her there. Later, as Karen and Rosario take a bath together, Karen comes up with a plan to convince Grace that she should leave, but Rosario wants to take a more direct report… and throws her down the stairs. Jack takes Will to his improv class taught by Zandra (Eileen Brennan) and asks each student to make an apology for something in front of the class. After an actress named Summers MacAbee (Margaret Scarborough) gives a heartfelt performance, Jack gets up in front of the class and gives a performance that Zandra ridicules. She then calls Will up and he reluctantly delivers an apology that is directed at himself. He tearfully apologizes to himself for always being too hard on himself and always trying to be perfect. Will does the second interview and knocks it out of the park. Grace is grumpy because she no longer has the servants waiting on her and thinks that Will’s apartment is a dump. 10/1/23
• 076. Loose Lips Sink Relationships – 10/25/2001
  • Jack gets a job at Barney’s department store, which prompts Will to tell Jack that people have been telling him that he looks like he could be a model. Meanwhile, Grace and Nathan go to get AIDS tests since they have agreed to be exclusive. This leads to a conversation about who has had more sex. Nathan has only had sex with five women, while Grace has been with 23. She thinks Nathan might be embarrassed by his number, but he says that he may have been with less people but has probably had more sex. They recalculate their numbers and Grace comes up with 282 encounters, while Nathan now has 3105… which is 1000 less than the real number. Jack begins his job at Barney’s and immediately looks down on the employee (Andrew Rosenbach) who is giving out cologne samples. Jack faces an issue when he writes his own schedule and gives himself Friday off so that he can perform in one of his acting class’s showcase, but his manager Dorleen (Parker Posey) says that he should never ask to be off on a Friday. When Will stops by, Dorleen tells Jack that she is attracted to him. Jack agrees to get her a date if she will give him off the Friday he needs. Will notices that Dorleen keeps staring him down, so Jack tells him that she is considering using him as a model at Barney’s. Jack then has Will give her some flowers that he says were delivered for her, so naturally Dorleen thinks they are from Will. When she invites Will to come back into her office, Will again thinks that she wants him to audition to model, but nearly flips out when he goes into her office, and she is half naked. When Grace asks Karen about the giant difference in their numbers, she tells Grace that is likely because people like having sex with Nathan, but people don’t like having sex with her. Later, Nathan also asks Karen about the difference in their numbers, so she tells him that sex is likely all he has to offer. After Jack’s like becomes apparent to Dorleen, Jack is relegated to offering samples. Grace becomes hellbe3nt on giving Nathan good sex, while Nathan is hellbent on avoiding sex altogether so that she can get to know more about the real him. She winds up chasing Nathan around Will’s apartment. Will tells them both not to take relationship advice from Karen and convinces both of them that their relationship is fine. They wind up bouncing around the room as Nathan chases her back to the bedroom, leaving Will to surmise how crazy straight people are. 10/1/23
• 077. The Rules of Engagement – 11/1/2001
  • Will catches Jack and Karen eavesdropping on Grace and Nathan as they make love in the bedroom. While they are having sex, Nathan proposes that they get married. Grace storms out of the bedroom because she is furious that he proposed in such a way. Grace throws everyone else out of the apartment and then tells Nathan that she didn’t find his proposal charming or spontaneous. That night they have dinner together, and Grace makes it clear she doesn’t want to talk about the proposal, so they wind up with nothing to talk about. She starts to get worried that since the proposal, there has nothing but weirdness between them. She looks to her friends for advice, and Will asks her if she would have said yes if he has asked her to marry him the right way. He suggests that Grace ask him to marry her. She decides to go for it and prepares a nice meal at the apartment for him. Karen loans her some expensive jewelry to wear for the occasion. Meanwhile, Nathan and Will have drinks at the Tight End gay bar, and Nathan gets mad when someone sends Will drinks since they could have easily been together. Nathan also witnesses a gay man (Dean Cameron) propose to his boyfriend (Shane Partlow). Nathan wishes that it has been that easy for him to propose to Grace and decides to go talk to her. Will rushes ahead of Nathan to tell Grace that Nathan is going to propose to her. Will tells her to drop a hint that marriage is back on the table. She does this by asking him how seating should be at a dinner party for the two of them, Will, and Marry – ie. “Will, You, Mary, Me”. When he says these words, she immediately accepts the proposal. When he acts confused by it all, Grace asks him to marry her. Nathan declines the proposal because he thinks it should have been easier the first time, and if they were meant to be together, she would have jumped at the chance when he first asked. She realizes this means he is breaking up with her. Will returns to comfort a sobbing Grace. Sam Pancake is the bartender. NOTE: Jordan Feldman is billed as Fred Homosexual but does not appear in the episode. 1/27/24
• 078. Bed, Bath, and Beyond – 11/8/2001
  • Grace is so depressed after her breakup with Nathan that she can’t seem to get out of bed, even when Will tries to cheer her up with Italian fashion magazines. After Will leaves, Jack tries to cheer her up as well by performing one of his medleys of songs from his new show Jack 2001, but this only reduces her to sobbing. Jack is thrilled that he was able to move someone to tears with his art. Will throws him out when he gets home. Karen then shows up and finds Grace reading notes that Nathan left for her, one of them being a note that they need milk. Karen offers to let Grace pretend that she is Nathan so that she can role play what she’s like to say to him. When Grace starts talking about how much she misses having sex with him, Karen winds up kissing her passionately… then gets embarrassed and leaves. Grace finally gets out of bed and finds Will, Jack, and Karen dancing in the living room. She is finally feeling better after three days in the bed, but then she hears a phone message from a travel agent who is book a trip for Nathan to the Bahamas with a girl named Susie. This sends Grace right back to bed. This time she climbs under it to look at her old childhood slides. Karen calls Rosario over to try and help Grace get out of bed with a hose, and winds up getting sucked into watching Grace’s slide show. When Rosario leaves to go get popcorn, the three of them drag Grace out of bed and put in her in the shower with her clothes on. Grace doesn’t want any part of it and tells them all that they are much stronger than her, but she needs to have her time in bed to deal with things her way. She climbs bak into bed soaking wet. Will comes in and admits that he has only deluded himself to think he’s over Michael, and Karen admits that she’s not okay with Stan being in prison and leaving her lonely at home. Jack also admits that he jumps from one relationship to another but is mostly upset that Grace didn’t mention that he is a dancer in addition to be an actor/singer. They all wind up climbing in bed with her and watching the slide show. Eventually Grace is able to pull herself out of bed, leaving the other three sleeping in it. 1/27/24
• 079. Star Spangled Banter – 11/15/2001
  • Jack is excited because he has gotten audition to play a corpse in the TV series Six Feet Under. Meanwhile, Will encourages Grace to donate to the City Council candidate Ted Bowers (Douglas Sills), simply because he is gay. However, when she starts wearing his campaign button, she is criticized by neighbor Mrs. Friedman (Anne Meara), who makes Grace aware that there is also a female Jewish candidate named Judy Green (Cynthia Mann Jarmin). While Jack is planning his watch party if he gets the corpse role, he finds out that his son Elliot doesn’t like Karen, and furthermore, that Karen doesn’t like Elliot. Not wanting to break apart his ‘movie star’ family, he takes Elliot over to Karen so they can work things out. She thinks he is a goody-two shoes, so he convinces her that he can be a bad boy by making prank calls. Karen shows him how to really make prank calls by phoning an injured Rosario and claiming to be the physical therapist, ordering her to do neck rolls. Will and Grace argue over the candidates, with each of them insulting one another. Grace says that Will doesn’t act gay, while he says that Grace doesn’t act like a woman. They end up reconciling, with each agreeing to support their own candidate, but they run into issues again when they each have agreed to hold a fundraising party at the apartment that night. They decide to hold the fundraiser together with each candidate making speeches to the group, which both turn out to be racist and misogynistic. They agree they don’t deserve to vote since neither bothered to figure out what their candidate represented. However, Jack has found a black candidate, so they head out to vote for him. When Jack picks up Elliot, he tells Karen he didn’t get the role because one of the guys on the set turned him on, so he didn’t appear ‘entirely’ dead. He is please, however, that Karen and Elliot have come to terms with each other. Rosario phones Karen and tells her that she is her pharmacist and since she took some of the wrong pills, she has to contort herself in various ways to counteract the potential side effects. NOTE: Michael Taylor Gray is credited as Ned but does not appear in the DVD version of the episode. 6/13/24
• 080 & 081. Moveable Feast – 11/22/2001
  • Over the phone, Will, Jack, Grace, and Karen discuss the plans to have Thanksgiving at Will’s apartment, but as they put one another on hold and speaking to each other, they all realize they have places to stop that day, and they ultimately agree to do each visit together, and then return to the apartment for the dinner. When they finish the discussion, Jack leaves his friend Lawrence (Clinton Leupp), who he had put on hold, hanging. On Thanksgiving Day, Karen shows up with Rosario so that she can stay at the apartment while they are out for the afternoon to baste the turkey. She immediately starts picking at it and eating little pieces of it. They decide to bring a timer and set it for one hour at each location so that they can all leave right on time. Their first stop is at prison, where Karen brings Stan a turkey to enjoy for the holiday. After just twenty minutes, she comes out and gets back in the car with the others and tells them that Stan has told her that it is not fair to make her wait for him, advising her to have sex with other men. Karen can’t get this off of her mind for the entire day. Next, they stop at Grace’s Aunt Honey’s (Lainie Kazan) place to see her family, including her mother who is depressed that she didn’t get the role in the stage production of Queen Leer. Grace asks everyone in advance not to tell her mother that she had broken up with Nathan, as she doesn’t want her mother saying that she told her so. Grace introduces her friends to Aunt Honey and Uncle Sid (Kenneth Mars), Aunt Reba, Uncle Joe, Uncle Funny (Murray Gershenz), and her mother Bobbi’s pianist Julius (Neil Vipond). Grace tells her mother that Nathan is spending the holiday with his own family. While Will struggles with a conversation with Sid, and Karen and Honey discuss committing adultery, Jack tries to comfort Bobbi after losing her role by telling her that Nathan and Grace broke up. Bobbie immediately jumps at the chance to rub it into Grace’s face and tell her that she told her so. Grace then tells her mother that she’s a terrible actress and wishes that she had told her sooner so that she could have said “I told you so” about her losing her part. The gang then leaves and picks up Elliot on the way to see Jack’s stepfather Daniel (Beau Bridges), who wants to meet Elliot for the first time. Jack has a lot of resentment toward Daniel and thinks that he never accepted Jack’s homosexuality. Daniel gets along well with Elliot and teaches him three-card monte and buys him a football. Jack wants to leave as soon as possible, but then decides to tell Daniel what he’s always wanted to say. Unfortunately, the bell goes off, so Jack is ready to leave immediately. As they head over to Will’s mother’s place, Will warns everyone that his family is the most dysfunctional of all. They arrive and meet Will’s brother Paul (Jon Tenney) and his wife Peggy (Helen Slater). Will’s mother Marilyn (Blythe Danner) is persnickety and difficult, and she is also upset that Will’s father went on a business trip during the holidays. Will’s Uncle Winnie (Gene Elman) is on so much medication, he scarcely knows where or who he is. When a plumber named Nick (Nick Offerman) arrives to repair the garbage disposal, Karen decides he may be the man she wants to have sex with. She flirts with him as he does his work, and he eventually becomes receptive to it. She grabs him and kisses him, but then slaps him immediately afterward. Then she repeats the process with another kiss and another slap, insisting that she is a married woman. Paul tells Will that he and Maggie are leaving in the middle of dinner, but Will objects and says it is his turn to stay. They argue over who is going to stay, and Paul suggests that their mother pick who stays. Will is sure it will be him, but she surprises him and tells him that Paul should stay. Although it lets Will off the hook, he is hurt that she picked Paul. When they arrive back, they all sit down to eat the turkey, that Rosario has carefully prepared to hide all that she has eaten off of it. However, before they start eating, they all realize that they are not happy with how they left things with their family members. They agree to make another round to each place and give themselves two minutes to say what they need to. They start at the jail where Karen tells Stan that she will not be happy sleeping with anyone else because he is the only person she loves. Grace returns to talk to her mother and tells her that she feels horrible, but her mother always telling her that she told her so really has started to get to her. Her mother promises to never say it again, even when Grace brings up all the things she has been right about. Grace thanks her for being so understanding, but as soon as she leaves, her mother sings her “I told you so” song and does her little dance. Over at Jack’s stepfather’s hotel, Jack berates him for being such a better father to Elliot than he ever was to him. Daniel tells him that he had a hard time understanding him since he seemed to speak his own language as a kid. He tells Jack that he has changed and wants to get to know him now. Jack likes that idea and says he will accept his gift now. It turns out to be a box of cash, so Jack realizes he might actually know him better than he thought. They go to Will’s mother’ place, where Paul has already left. She tells Will that she told him to go home and be with his family. She explains that she doesn’t have favorites, but if she did, Will knows how it would be. She says she can ask Paul to stay in front of him but could have never asked him to stay in front of Paul. She tells him that she will be fine alone with Uncle Winnie and sends him to be with his friends. As they drive home, they are all starving, and Will tells them how great the turkey will be, not knowing that Rosario is currently asleep on the couch after having eaten it all. NOTE: This is a one-hour episode that aired in two parts in syndication. 10/17/24
• 082. Stakin’ Care of Business – 12/6/2001
  • Will, Grace, and Jack are working out at the Crunch gym, when Jack reveals that he’s come up with the motivational phrase “Stake It!” Meanwhile, Will spots an old one-night-stand named Mitchell (Patrick Breen), who Jack and Will refer to as ‘Cuddle Bum’. Will ignores him and tells Jack that he was rebounding from his breakup and blew him off. Karen is too busy to fix the broken elevator that keeps sticking because she is watching a moving man (Josh Temple) in action as he is clearing out the building next door. Grace mentions that she had always wanted to expand the business into that building, and Karen tells Grace that she should have asked her for the money. When Grace does ask her, Karen insists that she give her a business presentation. Grace says that she’d rather go through a bank, but when she is quickly turned down, she returns and promises a presentation to Karen. Will meets another guy named Curt (Dan Gauthier) at the gym and they arrange to go out together. However, several days later, Curt won’t return any of Will’s calls. Jack hears from the gym gossip Marcy (Bess Meyer) that Curt is avoiding his late date, whom he refers to as the ‘Nibbler’. Will is offended so he goes and sees Curt at the later time that he is now showing up at the gym. Curt says that he was just getting out of a relationship and didn’t want anything serious. Jack points out the similarity between what is happening to Will and what Will did to ‘Cuddle Bum’. Will realizes the irony himself, so he goes to Mitchell to apologize… and learns that Mitchell is actually the boyfriend of Curt, with who he has now reconciled. Grace makes her presentation to Karen, but Karen turns her down. In retaliation, Grace won’t let Karen out of the elevator when it sticks, forcing her to make a presentation as to why she should be free. After leaving her there for a couple of hours, Karen finally admits that Grace’s goal simply didn’t make business sense, and explains her reasoning with astute business logic. She tells Grace that she would rather think that Karen is just mean than to have her dream crushed. Grace lets her out and gives her a hug, but Karen then forces her into the elevator and leaves her stranded there. When Jack hears a personal trainer (Ashley Borden) use his phrase “Stake It,” he nearly freaks out and complains to Will. He later comes up with a substitute phrase “Stake It, U.K.!” which quickly catches on. 6/13/24

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