SEASON 1 – CBS
Created by David E. Kelly.
Theme music by Erica Weis and Orr Rebhun
- 001. Pilot – 9/26/2013
- Simon Roberts (Robin Williams) and his daughter Sydney (Sarah Michelle Gellar) run the powerful advertising agency Roberts + Roberts in Chicago, with Simon being a happy-go-lucky jokester who was once the top in his field, and Sydney being more success driven and focused. Also on the staff are the charming womanizer copywriter Zach Cropper (James Wolk), the neurotic Andrew Keanelly (Hamish Linklater), and seemingly dimwitted assistant Lauren Slotsky (Amanda Setton). The team has a meeting with McDonald’s representative Hannah Sharples (Gail O’Grady), who is ready to fire the team until Simon promises that they can revive the You Deserve a Break Today jingle from 1972, but with a contemporary wholesome singer. Simon and Zach approach Kelly Clarkson (herself) to do it, but she says she is trying to re-brand herself with a sexier image. Simon manages to get her into the studio where she and Zach sing a sensual song called It Ain’t the Meat, It’s the Motion, before trying to pivot her to the original jingle, but she doesn’t bite and walks out on the session. Simon feels he’s failed, but Sydney approaches Kelly at her family dinner, and after Kelly forces her to sing the song in front of the restaurant, she agrees to perform the jingle. Simon is impressed with Sydney, who says she learned to take the leap from him. 12/14/16
- 002. The Spectacular – 10/3/2013
- Sydney heads up a campaign for Windy City Coffee, who is looking for something spectacular. She doesn’t think she has it in her, but comes up with a giant three-story outdoor display of coffee pouring from a carafe into a cup. Meanwhile Andrew gets jealous when it is clear that Simon favors Zach by giving him a leather jacket after a successful photo shoot that they both worked on. Simon works on raising ducks in his office to stock Arrowhead Pond that has recently been restored, and in order to show Andrew his appreciation for helping with the giant carafe, he lets him help raise the ducks. The Windy City Coffee brass are pleased with the display… until the winds picks up and dousing everyone in the crowd with coffee. Zach starts to feel jealous that Andrew and Simon are bonding over the ducks even though Andrew doesn’t really think it’s a great honor until finding out that the Arrowhead Project is really important to him since he feels like he destroyed the pond when he did a Pop Rocks promotion in it in the 1980’s, which also consoles Sydney that her father had experienced failures as well. Sydney alters the direction of the next Windy City Coffee ad by shooting a commercial advertising the ‘killer coffee’ in horror movie style, which the company execs Ted (Mark L. Taylor) and Kyle (Brent Jennings) find edgy. Andre has trouble getting the ducks to leave his side to swim into the newly dedicated pond, but makes Simon proud by leading them into the pond. Ashley Dyke is Mikayla. Gabriela Fresquez is TV reporter Christy Moon. 12/14/16
- 003. Bad Dad – 10/10/2013
- Simon and Sydney pitch an ad campaign to Allstate called the Milestone Campaign revolving around parents and their children’s magic moments. Their first commercial is based on their personal history, featuring a father (Todd Robert Anderson) who throws his daughter (Courtney Taylor Burness) in front of the steering wheel while traveling down the freeway to teach her to drive. When a focus group approves it, but thinks that the father is terrible, Simon and Sydney start to re-thing their relationship, and Simon realizes that Sydney never learned to drive because of the incident. This prompts him to take her back out and try to teach a more traditional way. When she bumps her car into another father/daughter combo Mitch (John Marshall Jones) and Taylor (Teala Dunn) who think that Simon is terrible, Sydney comes to his rescue and realizes that she got all of her unconventional talent and imagination from the way he taught her. Meanwhile when Andrew picks up a girl named Claire (Jen Lilley), whom Zach just dumped, then goes after Zach’s discarded potato chips and advertising ideas, Lauren starts referring to Andrew as Zach’s remora – the fish that hang around sharks in order to get its leftovers. Zach ends up turning down a date with Claire because of this…until Lauren realizes that Zach is actually Simon’s remora himself. J.D. Walsh is Randall, the head of the focus group. Dana L. Wilson, Tom Ayers, and Rodney J. Hobbs are on the focus group. Rod MacLachlan is Terrance with Allstate. 12/29/16
- 004. Breakfast Burrito Club – 10/17/2003
- Simon forces Sydney to take a vacation, so she plans to take off for Hawaii for a ‘possibly’ lesbian women’s group tour. However when the staff experiences writer’s block trying to prepare an ad campaign for a breakfast burrito company, she delays her flight to try and help. Meanwhile Zach thinks he might be falling in love with a girl named Natalie (Michelle LaRue) but hates it, and Andrew gets back with his ex-girlfriend Nancy Norris, who controls him and forces him to wear Cardigan sweaters. During their late-night brainstorming session, Simon forces Andrew to burn his cardigan which starts a fire that requires the firemen to come. Sydney and Andrew’s clothes get soaked and while they are changing, Andrew misreads Sydney’s signal and gives her a kiss, making things awkward between them. Simon leaves the office and goes to work at Jody’s Diner where he often gets ideas, but comes up with nothing, so the group simply just tries to have fun. Natalie joins Zach, and Zach quickly realizes he no longer likes her. Simon notices that Sydney is jealous when Andrew gets a call from Nancy, causing Sydney to wander if she is a ‘cheat’. This gives Simon idea for the campaign… ‘cheat on your breakfast.’ Sydney admits she enjoyed the night and heads to Hawaii, squeezing Andrew’s butt on the way out. J. Kristopher is the firefighter. 12/30/16
- 005. She’s So European – 10/24/2013
- Roberts + Roberts is handling a new client named Helena (Saffron Burrows), who is introducing a new e-date site for seniors. Sydney has a ‘woman crush’ on her, but things get comfortable with Sydney when Helena sleeps with Zach… and then Simon. Meanwhile Andrew is put in charge of managing a voice-over performance by Fred Melamed (himself), who takes an instant disliking to Andrew and accuses him of being a stoned hippie. When Melamed completely botches a line, Andrew has to summon his courage to stand up to him, and by doing so, he gains Melamed’s respect. When Zach tells Simon that he won’t steal Helena away, Simon is offended that he even thinks he could. Sydney forces them all to confront Helena, who thinks their various relationships are normal, but she thinks they’re making things complicated. She agrees to stay with the firm… but then leaves with Fred Melamed. Hugo Armstrong is Carl. 4/9/17
- 006. Hugging the Now – 10/31/2013
- As the team works on a campaign for Paratis erectile dysfunction pills, Simon finds out he is being nominated for an Advertising Impact Award. Lauren recommends an advertising campaign to push for his win. One of his fellow nominees is Josh Hayes (Michael Landes), a former fellow high school student of Sydney’s on whom she had a huge crush. At the reception for the nominees Sydney finds out that Josh had a crush on her as well, and gives her a passionate kiss, something he had vowed he would do if he saw her again. Sydney begins dating him, but then finds out that Josh has taken out a similar ad campaign to push for his win, the idea she accidentally mentioned to him. Sydney breaks it off with him and becomes hellbent on suing him, but Simon talks her down. He ends up losing to Josh, but still has the respect of his staff, who take him out to show their admiration. Zach dances with Sydney and sings a karaoke rendition of Eternal Flame to her. Alan Rachins is Bud Lymsky. Abraham Lim is Josh’s secretary Mike. Mike Wickliffe is Paratis exec Judy. Brandon Gibson is the waiter. 4/9/17
- 007. Sydney, Australia – 11/7/2013
- As Simon and the guys struggle to come up with a pitch to Eddie (Ron Bottitta) and Grant (Jonno Roberts) from the Australian board, Sydney fends off an old boyfriend and former jingle-writer named Danny Chase (Josh Groban) who now sings for a band and wrote a song tribute to her called Sydney, You’re So Fine. At first, she just avoids him but when he shows up at the office, she rudely brushes him off. In a moment of frustration at the Australians, he sings them the original song as a jingle about Sidney, Australia. Simon convinces Sydney to come to one of Danny’s shows, where he gives her the cold shoulder and performs a new, more scathing song called I Thought I Knew You. Simon convinces Danny to give him the original song if Sydney will occasionally act cruel to him to inspire his muse. Meanwhile Sydney has been written up in Ad Age magazine and comes across as cold and aloof. After Sydney starts to believe it is true based on how she treated Danny, but Simon shares with her that her kindness had actually gotten him to stop drinking years earlier. Sydney and Danny work together on a hate-song for Australia, but then Simon remembers it is actually New Zealand who he hates. Don Fonss is Roland. 11/14/17
- 008. The Stan Wood Account – 11/14/2013
- Roberts + Roberts resurrects an old ad campaign for Dust-It starring an actor named Glen Hastings (Ed Asner), who played Mr. Finger in the commercials. Sydney takes the elderly Hastings around town to show him around, and although Sydney enjoys his company, she is taken aback when he kisses her at the end of their ‘date’. Meanwhile Simon’s business partner Gordon Lewis (Brad Garrett) questions the existence of Stan Wood wallpapering, which is Simon’s cover for an old friend named Pete (Barry Shabaka Henley) used car business. Pete’s business doesn’t bring in any money, but it is still a conflict of interest to have two used car salesmen on their accounts, so Simon is forced to dump him. Since he feels bad, Simon and the gang try to help Pete sell his cars. Andrew, a big fan of Mr. Finger, catches him being a dirty old man with Katie (Christine Garver), and blackmails into helping sell the cars as Mr. Finger. On their break, the gang manages to sell nearly every car, the last one being to Gordon, who has to boy his boyfriend Timothy one after he is caught snacking. Daisy Aitkens is the Mr. Finger maid. Carol Kiernan is Tammy. 11/14/17
- 009. Sixteen-Inch Softball – 11/21/2013
- With the upcoming 16-inch softball game coming up between the Creative and Accounts teams, Simon recounts his glory days of almost singlehandedly defeating Gordon’s accounts team when he hit five home runs. With this upcoming game there is more at stake, as they need to fire someone after losing an account and the individual will come from the losing team. Simon has difficulty recruiting anyone and refuses to play himself, admitting to Zach that he isn’t the slightest bit athletic and only managed to hit the homeruns because he was high on drugs. He eventually is coaxed into playing, and the team does well, with Gordon walking Simon every time he goes to bat. However after getting teased by everyone, he finally decides to pitch to a frightened Simon, who ends up throwing his back out on the first pitch. Meanwhile Andrew’s girlfriend Nancy (Brooke Lyons) doesn’t like Sydney because Andrew told her that he had once shared a kiss with Sydney, who tries her best to win Nancy over, even giving her a gift certificate for a spa day. She finally starts to get through to Nancy, although Andrew prefers that they don’t become friends. The point is moot however, when a foul ball that Sydney hits strikes Nancy in the head. Simon returns to the game, offering to bat now that he is on muscle relaxers given to him by a medic (Andre Ing). He hits a homerun and rounds the bases with a victory swagger… but in reality, is running the bases backward without ever hitting the ball, sliding into home as he comes in from the pitcher’s mound. Gordon refuses to accept the victory since he knows Simon was impaired, so they decide to make their decision like professionals… by competing in a pocket motorcycle jousting contest. Andrew designs a female elf named Fliz for Rice Krispies. E.J. Callahan is the janitor. 7/7/18
- 010. Models Love Magic – 12/5/2013
- Gordon hides his homosexuality from some traditional clients from Aunty Mary’s Pecan Pies named Harold (Lex Medlin) and Clyde (Lance Barber) and insists that Simon dial his personality back a notch when dealing with them. With a Victoria’s Secret model shoot going on at the office, Lauren tries on a ten-million-dollar fantasy bra, one which is fiercely guarded by humorless security guard Marvin Trank (Lavell Crawford) and can’t get it off. Meanwhile Sydney can’t respect from the models, Zach can’t make any headway with hitting on them, but Andrew is impressing them by doing card tricks. Model Adriana Lima (herself) threatens to leave when her shoot is delayed, and Sydney tries to assert her authority and disparages her intelligence, but Adriana proves herself more versed in literature than Sydney. Zach is able to undo the bra by making out with Lauren, and Andrew keeps the model from leaving by doing magic. Gordon refuses to leave dinner with the pie clients when his husband Timothy begs him to come home when a raccoon gets in the house and Simon feels they are selling out. But when the clients start putting down Sydney, Gordon comes to his defense and admits his homosexuality. The clients agree that Gordon and Sydney will be going to hell, but find the lesser of all other agencies’ evils. Elecia Perkins, Ludi Delfino, Brittney ‘ShaRaun’ Brown, and Raquel Zimmerman are models. P.J. Ochlan is the Matre D. Special K Daily, Ant Atkinson, and Hi-Lite Bruton appear with the Harlem Globetrotters. 7/7/18
- 011. The Intern – 12/12/2013
- Roberts + Roberts received an entitled, spoiled intern named Kelsi Lasker (Ashley Tisdale), who is preoccupied with texting and fighting with her roommate Brooke (Brenda Koo) over who gets the bigger room… but is also the daughter of Martin Lasker (Jim Holmes) who has a $30 million account with them. After Kelsi ruins a sales pitch for a non-alcoholic wine with execs Larry (John O’Brien) and Phil (Brian Stepanek), Simon and Sydney give her some coaching, which leads to Kelsi telling Sydney that she will be fine when her daddy gets her a job… just like Sydney did from her father. Sydney lets her have it, until Kelsi walks out and heads to a frat party. Fearing they’ll lose the Lasker account, they follow her and challenge her to a game of Beer Pong, during which Sydney gets drunk and sick. Unable to defeat her, they vow that they’ll convince Brooke to give up the bigger room if she won’t tell her father. They do such a good job of pitching it to Brooke, that Kelsi suddenly wants the smaller room, leading to a brawl in the conference room… just as Martin walks in. He ends up commending Sydney for her hard work and confesses that he had hoped that her example would rub off on Kelsi. Meanwhile, Lauren wants to quit her affairs with Zach, so she turns to Andrew to be her non-sexual buddy. As Andrew becomes attracted to her, Lauren begins sleeping with Zach again… noting that the two of them together are the perfect man. When Andrew and Zach find out, they break it off with Lauren, who realizes she has no interest in sleeping with Zach if she hasn’t had friendship time with Andrew. Lauren hopes that things will look up for Andrew… and they quickly do when Kelsi asks him out in order to get revenge on her father. Teddy Lane Jr. is the security guard. Ari Stidham is Ari. 2/4/19
- 012. The Face of a Winner – 1/2/2014
- Simon challenges the team to think outside the box with their next ad campaign assignments, so he gives the girls the violent video game Medal of Glory to try and win the accounts of its creator Jerome (Lenny Jacobson) and Squirrel (Steven Boyer), while the guys get the Zen-Phoria spa. Sydney becomes addicted to the game. while Andrew burns his face and Zach numbs his mouth by trying to use the spa products. Sydney leaves the office with the game and heads to a gaming establishment. The gang tries to stage an intervention by creating avatars and entering the game… but she kills all of their characters. Simon realizes that Sydney is actually addicted to winning, since he had always let a young Sydney (Rachel Rodier) win at everything. When Sydney realizes how bad she looks from playing for four straight days, she is inspired to present a pitch revolving around her addiction to the game, which wins her the account. Zylan Brooks is the Zen-Phoria executive. Thomas Fowler is Desmond. 2/4/19
- 013. Outbreak – 1/9/2014
- Roberts + Roberts are brought in to do damage control when the Randi Jenkins doll (voice of Kiki Levine) from the Girlfriends doll series says “quiero Mommy” and it sounds like “kill Mommy.” Simon proposes a doll ‘apology tour’ and Lauren volunteers to head it up, and has the idea to bring in the little girl named Lily (Morgan Bastin) who was filmed on YouTube exposing the doll’s flaw. At the meeting held in one of the Girlfriends stores, it becomes obvious that the doll representative Garrett (Larry Sullivan) believes the doll is alive. Andrew on the other hand is creeped out by the doll, so the group plays a joke on him by fixing one of the dolls to say threatening things to him. After a little girl (Lily Bigham) sneezes on Zach, and he starts to come down with a cold, it starts to spread around the office, Sydney quarantines him and the other sickies into a separate room. She wants to make sure she stays well as she’s met a pediatrician named Kyle (Brennan Elliot) and scores a date with him. Andrew is uncomfortable with her going on a date, so he tries to spread germs with her to get her sick and miss the date. She catches him in the act and admits to Andrew that she’s scared to date him because if they don’t work out, she will lose her best friend. He shows his good will by retrieving her phone from the sick room. When Kyle shows up for their date and he sees Sydney cough lightly, he cancels the date in order not to risk sickness, and quickly meets another woman (Annalise Jorgensen) on the elevator. The apology tour is ruined when Lauren accidentally gives Lily the doll set up to scare Andrew and it speaks some scary dialogue. Simon manages to keep Girlfriends as a client by rigging a doll to put in a good word for them to speak to Garrett. Judith Moreland is Sandra. Helen Hong is Jenny. Kristine Johnson is Valerie the newscaster. Lauren Bulloch is the tea employee. 1/16/20
- 014. Simon Roberts Was Here – 1/30/2014
- Sydney is up in arms trying to figure out who subscribed her to Older Bride magazine, assuming it was either Zach or Andrew. Meanwhile the agency takes on new client Judy Mills (Stephanie Faracy) with Regal Kitty Cat Food, who are excited by the fact that Simon + Simon have hired a Quantitative Analyst – or “Quant” – named Colin (Sandeep Parikh) who drives his suggestions based on mathematical analysis. Judy also has a male cat named Princess live in the office for the week to inspire the team. Simon pitches his marketing idea involving cats behaving and deserving good food like humans do, while Colin’s data shows that they should focus on the easily removable cat food can lid. Simon offers a wager that each will come up with a marketing campaign for ice to be judged by Sydney, Zach, and Andrew. When their ideas are presented, they all choose Colin’s ad. Simon is distraught and vows to move everything over to data-based, and also figures out that Colin had targeted the three judges specifically by planting subliminal messages to each person in the ad based on their computer browsing history. Sydney’s history showed that she in fact had been the one who ordered the Older Bride subscription, and Colin’s profile on her indicated that she would likely never get married, especially based on how close she had come with Princess. Zach and Andrew spraypaint one of Simon’s most successful billboard campaign’s with “Simon Roberts Was Here,” but a police officer (John Eric Bentley) thinks that Simon painted it and arrests him. On the day of presentation, Simon is late since he just got out of jail, but he brings fellow prisoner and transsexual Anastasia (Jazzmun) with him to the meeting to help illustrate that by combining Colin’s research with his creativity, you will get something special. His ad campaign does in fact focus on the easy open can, but is much more appealing than Colin’s, which excites Judy and her crew. Sydney is tempted to ask to keep Princess, but then realizes that her profile indicates that owning a cat is the first step to lifelong singledom. However Simon tells her that the future isn’t quantifiable, so she claims the cat anyway. When she arrives home, she finds an attractive new neighbor named Dylan (Daniel Bess) has moved in… and happens to be a veterinarian. John Duerler and Eric Zuckerman are the security guards who pass along the video of Sydney’s date with Princess. 1/17/20
- 015. Dead and Improved – 2/16/2014
- While working on a Rice Krispies campaign doo-wop jingle with the trio Calvin (Kelly Perine), Teddy (Marcus Henderson), and Wilson (Kenneth Brown), Simon gets word from Sydney that his jingle-writing colleague Conrad has died. Conrad’s daughter Melora (Missi Pyle) wants Simon to give the eulogy, but the problem is that he nor anyone else has anything nice to say about Conrad. Nevertheless, Melora wants a tribute full of pomp and circumstance that will be synonymous with the word ‘wow’ and has a quivering lip that Simon can’t resist. He tries to trade assignments with Andrew, who is working with overzealous Charmin client Mitchell Payson (Kurt Fuller) who wants Charmin to be used for everything that Kleenex is used for, but Melora won’t have it. Simon gets to work and brings in voice-over artist Fred Melamed (himself). Meanwhile Sydney finds out that Payson is being separated from his company for erratic behavior since his wife left him. When the meeting is terminated, Payson strips naked in the office and requests that Simon help reinvent him as he has done for himself. Simon tells Sydney that this upsets him, because he realizes that his life might all be about the pomp he has built around himself. She reassures him that he is awesome, and he goes on to produce an upbeat, satisfying, and emotional funeral that includes gospel singers, gift bags, a Fred Melamed introduction, and Simon talking about how Conrad’s biggest legacy is the way his daughter saw him through her eyes. This also touches Sydney who sees her father the same way. The pallbearers carry out Conrad to the bouncy tune of the The Glory of Love. 5/1/20
- 016. Zach Mitzvah – 2/27/2014
- Simon is trying to woo client Beth Minker (Cheryl Hines) with Bainbridge Motels, and when he finds out that she has lost her DJ for her son Noah’s (Joe West) Bar Mitzvah, he volunteers Zach to take over since it turns out that Simon had met Zach when he used to DJ them. He is okay with doing it, as long as noted Bar Mitzvah singer Zoe Gold (Jackie Seiden) isn’t performing as they had had a bad breakup. Simon arranges to hold the event at the office overlooking Chicago, to stay in the theme “Noah Loves Chicago.” However, Noah is disappointed because it is the play Chicago that he really likes. Sydney spots an attractive man named Owen (Steve Talley) at the party and agrees to have drinks with him afterward, but then winds up firing him when she finds out that not only is he a waiter at the party, but that he is eating the leftover food off of people’s plates. Owen refuses to leave and claims that she only fired him because she was embarrassed that she hit on a waiter. As their arguing escalates, they wind up kissing, and since he was crashing at his manager’s place and now has nowhere to live, Sydney agrees to let him stay on her couch. Simon winds up getting Zoe Gold as the singer when the other one’s daughter gets appendicitis, and Zach has a hard time coping. The party begins to fall apart when Zach reveals that he had been in love with Zoe, and she dumped him. He keeps pestering her to find out why and learns that she never loved him and was only having fun while they were dating. Simon and Sydney try to interrupt Zach’s emotional outbursts by getting the party to sing The Horah Song repeatedly. Beth eventually gets irritated when people start leaving the party after Zach disappears. Simon attempts to save it by telling jokes, but fails to impress anyone, including the cantankerous Aunt Sadie (Norma Michaels). When Zach notes the crestfallen Noah, he decides to treat him like the client and make the party better for him by singing All That Jazz from the play Chicago. Lauren gets high with some young partygoers and is hit on by a boy named Jaden (Skyler James Sandak). The Peppers are Jessica Press, Tia Robinson, and Lexi Brandt. Rick Cowling is a band member. 5/1/20
- 017. Heavy Meddling – 3/6/2014
- Simon is auditioning babies for an advertising campaign, when he makes it clear that he is hopeful that Sydney’s new relationship with Owen could mean grandchildren for him. Sydney however is trying to cope with a new live-in boyfriend, and afraid to go to the bathroom with him in the house, she keeps going to a tobacco shop where the owner forces her to buy cigarettes to use his facilities. Simon pushes the envelope even further by hiring Owen to work as a photographer for him. This means Sydney has to be on her best behavior – and avoid messy foods – at work as well. When Owen finds Sydney’s cigarettes, he questions her about her smoking habit, so she confesses the real reason she has them. Owen reciprocates by telling her some his secrets, including his fear of babies. This is horrible news to Simon, who quickly assigns him to photograph babies. When he and Sydney finally realize that they want different things, they decide to amicably part ways. Meanwhile while Zach is on vacation, Andrew partners up with another copywriter named George (Joshua Gomez), who pays Andrew a lot of compliments on his artwork. When Zach returns, he suddenly doesn’t seem so easy to work with, and thus Andrew complains about some of his behaviors. They agree to work with other people, with Zach choosing to work with the nerdy Peter (Christopher Carley). When he realizes he can’t capture the same chemistry with Peter, he is talked into begging Andrew not to make an advertising pitch with George, realizing that could mean they work together on a more permanent basis. Andrew obliges and comes back to work with Zach, leaving George to make the pitch by himself. Pramode Kumar is Jaleel. 8/13/20
- 018. March Madness – 3/13/2014
- Andrew head up designing a charity float for a kids charity to be in the Chicago St. Patrick’s Day Parade. With Simon being a recovered alcoholic, Sydney tries to keep all references to the holiday away from him. This proves difficult when Andrew’s six elementary school sisters Elaine (Jessica Chaffin), Molly (Carmella Riley), Eileen (Stephanie Cannon), Ellen (Lauren Pritchard), Helen (Anna Vocino), and Katherine (Jamie Denbo) make a surprise visit in hopes of camping in the office for the festivities. In order to keep them away from Simon as much as possible, Zach heads up taking everyone out drinking, and winds up injuring his eye and waking up in the office covered with makeup. Simon has finally had enough and orders Lauren and Blaine (Joe Nunez) to get rid of everything related to the holiday. Blaine understands that to include Andrew’s float as well. Andrew has also had enough and orders his sisters to leave. When Simon finds out that the charity was for kids and headed up by Kareem Abdul-Jabbar (himself), he and Andrew set out to rebuild the float, but quickly find themselves floundering as the deadline approaches. Andrew’s sisters come to the rescue and as teachers, help construct a nice replacement float. Meanwhile as Sydney and Zach are auditioning a model (Dana De La Garza) for a Dunkin’ Donuts promotion, the company spokesman Roger (Scott Klace) decides he wants a normal woman and chooses Sydney. As a former child actress who did commercials, she is ecstatic, but as soon as she leaves the room, Roger changes his mind and decides to ask Lauren to be the model. Sydney tries to take it in stride, and even gives her pointers to reward herself with candy each time she delivers the commercial line correctly. Unfortunately, this gets her too wired on sugar and she is fired. As everyone sits on the float together, Sydney admits that she was jealous of Lauren, who admits that she looks to Sydney as a role model. Jack Gamero is the child Cameron. 8/14/20
- 019. Danny Chase Hates Brad Paisley – 4/3/2014
- Sydney tries to introduce her new assistant Allie (Tiya Sircar) to the group, but Simon, Zach, and Lauren are too busy in a contest to see who can do the most shots of Devil’s Tongue’s barbecue sauce. The sauce is the family recipe of sisters Millie (Jane Edith Wilson) and Jane (Lisa K. Wyatt), and in order to woo them as clients Simon and Zach promise they can get Danny Chase to write them a jingle. This is before Simon is rushed to the hospital from all of the sauce he ate, so Zach has to wrap up the deal, and he does so by promising to get country singer Brad Paisley (himself) to sing the jingle. Chase is agreeable, but has a feud with Paisley, so will only agree to write the song if Paisley apologizes for something he did. Paisley is also agreeable, but claims not to know Danny Chase, and also states that he never apologizes. Zach, trying to think like Simon, tries to smooth it over by forging a letter from Paisley to Chase. Meanwhile Sydney demands that Zach not date Allie, as she is working out perfectly for her… as well as Lauren, who keeps snagging her to do odd jobs for her as well. However, she doesn’t give Andrew the same instructions and before she knows it, Allie is going out with him. Their date doesn’t go too well, and when Andrew tells her that he’s not interested, Allie is devastated, and the next day has to leave work in a flood of tears. Sydney insists that he take her out again and not be likeable so Allie can get over him quickly. It appears to work, because she is much happier and apologizes for not being professional the next day. Andrew admits that he’s glad they made him take her out, because he now seems to like her just fine… which also makes Sydney start to feel a little jealous. When Chase and Paisley find out that the apology letter has been forged, it leads to them to drudge up the reason for the dispute: Paisley had mocked Chase when he appeared on a reality show called American Country Star that he used to judge. This also leads to further fighting, culminating in Paisley punching Chase in the face. Not sure how to proceed, Simon advises Zach to stop trying to think like him and think for himself. He comes up with capping each bottle of sauce with a fist that plays the audio of the face punch when it is opened. The sisters love the idea, and they get the account. Baldeep Singh is Simon’s doctor. 11/29/20
- 020. Love Sucks – 4/10/2014
- Simon has a new girlfriend named Lily Schecter (Pam Dawber) who has written a book called 90 Dances, 90 Nations. He seems smitten and they plan a dinner date that he vows will be terrific. Meanwhile Gordon is on the floor sobbing, causing Sydney to trip over him and sprain her ankle. It turns out that he and Timothy (Jonathan del Arco) got into a fight, and he through Gordon out after twenty years of being together. One of the reasons is that Gordon lacks spontaneity, so Simon offers to coach him. He brings Gordon into their brainstorming session where they look at Smart Specs, eye glasses on which the wearer can browse the internet. Zach and Andrew find a set of keys in the elevator, and although Zach suggests they leave them there, Andrew feels he should find the owner. They turn out to belong to Jean Haskel (Sarah Baker) whom everyone refers to as the human tick because she attaches herself to anyone she comes in contact with. Although he tries to avoid her when he returns the keys, she spots him and forces him to hang out with her several days in a row. Zach and Lauren decide to pawn her off on someone more needy: Sydney, who is hobbling around the office on crutches. They steal Jean’s keys and lay them near Sydney, so Jean does in fact gravitate toward her. Sydney tries to resist, but when Jean gives Sydney sympathy for her sprain, she seems to embrace it. Simon has Gordon stay with him, and they invite Simon’s neighbors Neal (Ben Begley) and Anna (Jennifer Marsala) over to visit. Gordon is uncomfortable around people, but he appears to be doing well with chatting… until he figures out that Gordon is using the Smart Specs. Simon becomes disillusioned with love after seeing Gordon and Timothy fall apart, so he sabotages his own relationship with Lily and breaks it off, despite their delightful fancy dinner with David Copperfield (himself) performing impossible magic for them. Simon gets Gordon to perform at the gay karaoke bar his version of Wrecking Ball, which impresses Timothy and gets them back together. Simon returns to Lily’s apartment, but she shoots him down and tells him he behaved like an alien. Jeff Holman is the karaoke announcer. 11/29/20
- 021. The Monster – 4/17/2014
- Simon is hellbent on saving the East Naperville Library that he used to visit when he was a kid, thinking that local residents will vote down a tax that will force it to shut its doors. Gordon is concerned because they just lost the UPS account, and demands them not to do pro bono work, telling them that he and his team won’t receive a salary if they do. Simon gets the idea to introduce a villain who promises to host a book burning when the library is shut down, using Gordon’s face as said villain. Gordon is livid that he is being made into the monster, especially when people start recognizing him and pelting him with eggs in the street. Simon promises to reveal him as the hero after the library gets the votes it needs. Sure enough, the library is saved, but before Simon can introduce him as the hero who masterminded the campaign, Gordon accidentally sets a stack of book on fire outside the library. The crowd attacks and chases him in a scene reminiscent of Frankenstein. Eventually the truth comes out, and it serves the company well as new clients start pouring in. Even though Simon tells Gordon they make a great team, Simon announces that he’s sold the company to the Hamasaki Corporation. Meanwhile, Zach is jealous of the time that Andrew is spending with Allie, so in turn he starts spending time with Sydney’s boyfriend Dylan. Gordon points out to Andrew and Lauren that Dylan is obviously gay. It takes a while until Sydney figures it out, and even longer until Zach does. Zach, however, decides to continue being friend with Dylan, partially to try and keep Andrew jealous. Andrew, however, is more wistful about how much he misses hanging out with Sydney. Melody Thomas Scott is Flora the librarian. Reporter Gayle King is herself. Ukee Washington is a reporter. Phoenix Elkin, Ivy George, and Tri Pham are kids in the library. Corey Mendell Parker is the interview subject Trevor. Jill Lynne Johnson is credited as Amy. 3/21/21
- 022. The Lighthouse – 4/17/2014
- Simon does not want to sell the company to Hamasaki, but Gordon doesn’t agree and thinks the $47 million price tag is too good to pass up. When they can’t agree, they decide to call in the board to make the decision, a move that Simon is appalled by since once of the board members is his ex-wife Paige (Marilu Henner). She seems like a fun lady to everyone around, which is where she gets her nickname ‘the lighthouse’, and Sydney is particularly happy to see her, but Simon thinks she is selfish and has always disappointed Sydney. However, when the board splits down the middle on the vote of whether to sell or not, Simon is forced to hide his feelings and try and butter her up to vote his way. Gordon also tries to get on her good side, with as romantic gestures as he is capable. Paige keeps telling both of them that she is leaning toward their decision. Simon finally goes all the way and sleeps with her, which puts him over the top. Unfortunately, he sees Sydney and her getting closer, and Sydney getting particularly excited when she mentions moving back to Chicago and even going house hunting with her. When Simon finds out that Paige is planning to spend a year in Morocco, he berates her for being such a horrible mother. Meanwhile, Allie’s beautiful friend Megan (Gillian Alexy) comes for a visit, and Zach immediately falls for her and accepts her invitation to go out. This makes Andrew extremely nervous that Zach will use and abuse her, and then get him on the bad side of Allie. Zach promises to be a gentleman, and Andrew agrees to let them go out. After sleeping together, Megan invites Zach to attend a wedding with her, so he reluctantly agrees, remembering his promise. When he shows up for the wedding, he finds out that Megan is actually the bride and that she was just using him for a final one-night stand. Andrew is irritated with Allie for being a part of it. Sydney follows some advice that her mother gives her about going for Andrew, and Simon actually seconds the thought to go for it. As Simon and Paige are arguing over who gets credit for steering her toward Andrew, Sydney plants a huge kiss on Andrew and tells him that if he likes it to tell her, and if not, that they will never speak about it again. Apparently, his response is not a good one, as she comes out of the office asking her parents if she too can go to Morocco. Dan Amos is the wedding usher. 3/21/21
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