List of Spin City episodes

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The episode list for the ABC series Spin City.

In total, there are 145 episodes, with Michael J. Fox starring in the first 100 episodes, and Charlie Sheen starring in the last 45.

Season 1: 1996–1997[edit]

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Title Directed by Written by Original air date
1 1 "Prototype" Thomas Schlamme Gary David Goldberg & Bill Lawrence September 17, 1996
Michael Flaherty (Michael J. Fox) and his City Hall team grapple with a garbage strike and a political gaffe when the Mayor accidentally insults gay people. Mike's girlfriend Ashley (Carla Gugino) questions Mike's commitment to their relationship when he is nervous about them moving in together.
2 2 "The Great Pretender" Lee Shallat-Chemel Sarah Dunn September 24, 1996
Mike is named Sexiest Man in New York by Manhattan magazine and the staff must deal with Mayor Winston's problematic wife during an important dinner.
3 3 "The Apartment" Lee Shallat-Chemel Bill Lawrence October 1, 1996
The continuing dilemma of the garbage strike keeps Mike and Ashley too busy to spend time together at their new apartment. Stuart makes a blunder when left in charge of the office.
4 4 "Pride and Prejudice" Lee Shallat-Chemel Brian Buckner & Sebastian Jones October 8, 1996
During a television interview, Mike makes an insensitive joke about his working relationship with Ashley. Carter goes over Mike's head and encourages the Mayor to support a controversial policy on HIV. A reporter (Gretchen Mol) is attracted to James.
5 5 "The Rivals" Lee Shallat-Chemel Amy Cohen & Michelle Nader October 15, 1996
The Mayor feels responsible for the death of his predecessor. Mike and Ashley try to avoid their new neighbors.
6 6 "A Star is Born" Lee Shallat-Chemel Kirk J. Rudell October 22, 1996
The Mayor's low approval ratings sink even lower when the Winston Administration supports a nominee with a checkered past. Note: During the scene of Mike in his office with the mayor, you can see the Shotgun Microphone at the top of the screen.
7 7 "Grand Illusion" Lee Shallat-Chemel Amy Cohen & Michelle Nader October 29, 1996
Carter stages a mock wedding with Nikki, in protest of the Mayor's stance against same-sex marriage. Ashley is unhappy with the quality of her assignments at her new job.
8 8 "The High and the Mighty" Lee Shallat-Chemel Kirk J. Rudell November 12, 1996
Mike asks a powerful land developer (George Wendt) for a favor. As the Winston Administration celebrates a reduction in crime rates, Paul gets mugged.
9 9 "Meet Tommy Dugan" Lee Shallat-Chemel Tim Hobert November 19, 1996
A janitor at a local public school (Woody Harrelson) surprises the staff by winning the "New York City Mayor for a Day" contest. The Mayor tries to conform his image to the guidelines of a focus group. The second consecutive episode guest starring a Cheers alumnus.
10 10 "The Competition" Lee Shallat-Chemel Sarah Dunn November 26, 1996
The Mayor's staff compete with the City Council as to who can serve the most homeless people on Thanksgiving. James tries to break up with his high school sweatheart (Jennifer Garner) who visits from Wisconsin. (Guest stars: Stephen Colbert as Frank, and former mayor Ed Koch as a city councilman.)
11 11 "Dog Day Afternoon" Lee Shallat-Chemel Jeff Lowell December 10, 1996
Paul and Carter lose the body of a beloved police dog on its way to burial. Mike buys an air hockey table to help the staff relax.
12 12 "Criss Cross" Lee Shallat-Chemel Brian Buckner & Sebastian Jones December 17, 1996
When the Mayor comes down with a cold, Mike must debate Ashley on a political talk show.
Last appearance of Ashley.
13 13 "Bye Bye Love" Lee Shallat-Chemel Kirk J. Rudell & Bill Lawrence January 7, 1997
Mike breaks up with Ashley. Paul sets a New Year's resolution to be less gullible.
14 14 "Starting Over" Lee Shallat-Chemel Jeff Lowell January 14, 1997
Michael is uncomfortable being newly single with assistant DA Danielle Brinkman (Courtney Thorne-Smith). Paul meets the president of his fan club, Claudia Sacks (Faith Prince), who has arranged the "group's" first meeting. Carter and Stuart have a little too much to drink and end up in an uneasy situation.
First appearance of Claudia.
15 15 "Gabby's Song" Lee Shallat-Chemel Jeff Lowell & Tim Hobert January 28, 1997
Mike's attempts to woo a new member of the City Council (Constance Marie) are thwarted when she decides to play dirty. Claudia tries to seduce Paul.
16 16 "Kiss Me, Stupid" Lee Shallat-Chemel Sarah Dunn February 11, 1997
Carter is reunited with his ex, Spence (Luke Perry), who is engaged to a woman. Mike goes on a disastrous first date with Nikki's friend Veronica (Kim Dickens).
17 17 "An Affair to Remember" Lee Shallat-Chemel Michelle Nader & Amy Cohen February 18, 1997
As the Mayor's 50th birthday approaches, the media react to rumors he is having an affair. James edits the Mayor's birthday video, which features cameos by Rosie O'Donnell, Patrick Ewing, David Letterman, Larry King, the cast of Rent, and George Stephanopoulos; whom nobody believes that Paul is good friends with.
18 18 "Snowbound" Lee Shallat-Chemel Brian Buckner & Sebastian Jones February 25, 1997
A massive blizzard hits New York. Mike is approached by a high school crush (Amanda Peet) for a one-night stand. Carter and Stuart get trapped in the boiler room. Paul lands in hot water over a remark about the Mayor.
19 19 "Striptease" Lee Shallat-Chemel Jeff Lowell & Tim Hobert March 4, 1997
Mike dates a law student (Cynthia Watros) who happens to work part-time as a stripper. Nikki uses the advice of a guy she is dating to freak out Stuart.
20 20 "Deaf Becomes Her" Lee Shallat-Chemel Kirk J. Rudell & Sarah Dunn March 18, 1997
When an office temp's attempt at sign language offends the deaf community, a leading advocate (Marlee Matlin) for deaf rights threatens to demonstrate at City Hall. Claudia moves in with Paul after he suffers a leg injury.
21 21 "Hot in the City" Lee Shallat-Chemel Jay Scherick & David Ronn April 1, 1997
Mike's ex-girlfriend Carrie (Daphne Zuniga) desperately wants to bear his child, so she steals his sperm. A gaffe by the Mayor threatens to break up the reunion of a popular rock band.
22 22 "Bone Free" Lee Shallat-Chemel Michelle Nader & Amy Cohen April 29, 1997
Rumors about the Mayor's health abound, when he refuses to stand during a press conference. The guys don't approve of Nikki's freeloading screenwriter boyfriend.
23 23 "The Mayor Who Came to Dinner" Lee Shallat-Chemel Tim Hobert & Kirk J. Rudell May 6, 1997
Mike must deal with a new roommate: The Mayor. Isaac Mizrahi helps the Mayor with a charity fashion show, and gives Nikki the chance of a lifetime.
24 24 "Mayor Over Miami" Lee Shallat-Chemel Teleplay by: Brian Buckner & Sebastian Jones
Story by: Sarah Dunn
May 13, 1997
The Mayor deals with his recent separation by taking Paul on a trip to Miami, leaving Mike to cover for him at City Hall. Stuart is strangely affected by his new girlfriend (Marin Hinkle).

Season 2: 1997–1998[edit]

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Title Directed by Written by Original air date
25 1 "Paul Flew Over the Cuckoo's Nest" Andy Cadiff Bill Lawrence September 24, 1997
Mike is attracted to his opponent, Mayor's wife's divorce lawyer, Laurie Parres (Paula Marshall). The press thinks that Paul has suffered a nervous breakdown, so Michael hires a psychiatrist to pronounce Paul sane, but Dr. Benjamin unexpectedly commits Paul to an institution.
26 2 "Porn in the U.S.A." Andy Cadiff Jeff Lowell October 1, 1997
After announcing a crackdown on public access pornography, the Mayor is caught on tape, entering an x-rated video store. Mike and Nikki fight over who can spend time with Laurie. Stuart and James lust after Paul's mom (Raquel Welch).
27 3 "Wonder Woman" Andy Cadiff Jay Scherick & David Ronn October 8, 1997
Mike stalks Laurie, and meets her mother. Stuart changes the engine of James' remote controlled boat. Mike tells Laurie he loves her, which left her speechless.
28 4 "The Goodbye Girl" Andy Cadiff Gayle Abrams October 15, 1997
Mike has to make a decision about his relationship with Laurie, after he discovers that she doesn't want a serious commitment. The Mayor falls for a younger woman (Marla Maples). (First Appearance: Stacey (Jennifer Esposito))
29 5 "In the Heat of the Day" Andy Cadiff Stephen Godchaux October 22, 1997
While jogging, Carter is mistaken for a mugger and arrested in Central Park. Paul is afraid he's a racist.
30 6 "Radio Daze" Andy Cadiff Kirk J. Rudell October 29, 1997
When a radio shock jock challenges the Mayor to a mock election, Mike becomes determined to win at all costs. (Guest Stars: Regis Philbin and Kathie Lee Gifford)
31 7 "The Thirty Year Itch" Andy Cadiff Michelle Nader & Amy Cohen November 5, 1997
Mike goes to the Empire State Building to fulfill a promise made to his high school sweetheart (Tracy Pollan). The Mayor asks Carter to determine if his nephew is gay.
32 8 "My Life is a Soap Opera" Andy Cadiff Tom Hertz November 12, 1997
Mike dates a writer for All My Children and sees his personal life being portrayed on television. Stuart uses the rumor that he is gay as a way to get closer to the women at City Hall.
33 9 Family Affair (Part 1) Andy Cadiff Brian Buckner & Sebastian Jones November 19, 1997
Mike's mother (Meredith Baxter) comes to visit. The Mayor is photographed giving money to a known prostitute. Paul gets sued by the security guard who shot him.
34 10 Family Affair (Part 2) Andy Cadiff Jeff Lowell & Tom Hertz November 26, 1997
Mike's mother could be the key to clearing the Mayor from claims that he solicited a prostitute. Paul appears on The People's Court to settle his lawsuit. (Guest Stars: Former New York City Mayor, Ed Koch and Alan Dershowitz)
35 11 "They Shoot Horses, Don't They?" Andy Cadiff Laurie Parres December 10, 1997
The Mayor's daughter (Alyssa Milano) participates in an animal rights protest to get back at him. Paul arranges to meet his pen pal.
36 12 "Miracle Near 34th Street" Andy Cadiff Stephen Godchaux & Gayle Abrams December 17, 1997
The Mayor accidentally tells a little boy that there is no Santa Claus. James receives a care package from his parents.
37 13 "Same Time Next Year" Andy Cadiff Jay Scherick & David Ronn January 7, 1998
The staff all have trouble remembering what happened at the Mayor's New Years Eve Party.
38 14 "The Paul Lassiter Story" Andy Cadiff Bill Lawrence January 21, 1998
Mike tries to put his life in perspective as he waits for the results of his physical. Paul tries to convince the Mayor to put him in his autobiography. (Guest Star: Donald Trump)
39 15 "Gentleman's Agreement" Andy Cadiff Tim Hobert January 28, 1998
The Mayor comes under fire for his membership in a club that doesn't allow women. Mos Def guest stars.
40 16 "Deaf Man Walking" Andy Cadiff Jeff Lowell February 25, 1998
The Mayor tries to hide the fact that he's lost his hearing. After helping Stacey move into her own apartment, Stacey's grandmother puts a curse on Mike.
41 17 The Marrying Men Andy Cadiff Michelle Nader, Amy Cohen March 4, 1998
Paul decides to propose to Claudia. Laurie returns in hopes of restarting her relationship with Mike.
42 18 One Wedding and a Funeral Andy Cadiff Tom Hertz March 11, 1998
Mike announces that he and Laurie are engaged. Paul gets cold feet about asking Claudia to marry him.
43 19 "A River Runs Through Me" Andy Cadiff Laurie Parres March 18, 1998
The staff are required to take drug tests. The Mayor breaks a Native American artifact before it can be donated to a museum.
44 20 "The Pope of Gracie Mansion" Andy Cadiff Stephen Godchaux April 1, 1998
After the Pope visits City Hall, the Mayor tries to be more holy and Mike feels guilty for his sinful ways in City Hall.
45 21 "Bye, Bye, Birdie" Andy Cadiff Brian Buckner & Sebastian Jones April 29, 1998
The men and women play pranks against each other at Paul and Claudia's bachelor/bachelorette parties. Mike, James, and Carter get trapped in a hardware store when it is robbed.
46 22 "The Lady or the Tiger" Andy Cadiff Gayle Abrams & Kirk J. Rudell May 6, 1998
Mike dates an insane magician, and then has trouble ending their relationship. Stuart and Carter open a gay bar.
47 23 "Single White Male" Carl Lauten Michael Lisbe & Nathan Reger May 6, 1998
Financial troubles cause Stuart and Carter to become roommates.
48 24 "The Paul-Bearer" Andy Cadiff Tim Hobert May 20, 1998
Mike accidentally mixes up the date for Paul's wedding with the date of a city function, causing the chapel to be double booked. Carter has trouble confessing his sexuality to his childhood priest.

Season 3: 1998–1999[edit]

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Title Directed by Written by Original air date
49 1 "Dead Dog Talking" Andy Cadiff Tom Hertz September 22, 1998
City Hall prepares for the mayor's bid for re-election announcement. Carter adopts his family's 19-year-old dog. And, Paul teaches Stacey how to get a sick day without being sick. Conan O'Brien guest stars.
50 2 "There's Something About Heidi" Andy Cadiff Amy Cohen & Michelle Nader September 29, 1998
After Mike's picture with model Heidi Klum is in the tabloids, people assume he's dating her. Nikki reveals to Carter that she has a secret crush on Mike. The Mayor can't stop laughing at inappropriate times.
51 3 "Gone with the Wind" Andy Cadiff Stephen Godchaux October 6, 1998
Mike must keep his relationship with Heidi Klum a secret. Paul creates an incident involving a fan and ashes.
52 4 "The Deer Hunter" Andy Cadiff Brian Buckner & Sebastian Jones October 13, 1998
Mike is handling a political donor in the hope of receiving a donation. Stuart has been named as Stacey's boss for the day.
53 5 "It Happened One Night" Andy Cadiff Gayle Abrams October 20, 1998
Mike considers adopting an abandoned baby. Cameo appearances by Mike's former girlfriends.
54 6 "Three Men and a Little Lady" Andy Cadiff Tim Hobert October 27, 1998
Mike tries to improve the Mayor's macho image. Stuart's girlfriend takes over Carter's apartment. (First appearance: Deidre (Beth Littleford))
55 7 "An Officer and a Gentleman" Andy Cadiff David S. Rosenthal November 3, 1998
Mike's childhood friend returns from a stint in the Navy to reveal he's gay and Mike is jealous when Carter starts dating him. Guest star: Lou Diamond Phillips
56 8 "Quest for Fire" Andy Cadiff Jay Scherick & David Ronn November 10, 1998
Mike suggests a dinner date with Nikki's fictitious boyfriend named Arthur. Mike tries to take a vacation, but the Olympic torch-carrier gets lost in New York; and Paul tries to fit in when he moves into Janelle's Harlem neighborhood.
57 9 "The Kidney's All Right" Andy Cadiff Bill Callahan & Philip Wen November 17, 1998
The mayor makes a promise to give a child (Frankie Muniz) his kidney. Guest stars: Jeff Gordon and Jayson Williams.
58 10 "Gobble the Wonder Turkey Saves the Day" Andy Cadiff Tom Hertz November 24, 1998
The mayor hosts a televised Thanksgiving dinner. Stacey has a startling moment with Stuart.
59 11 "Local Hero" Andy Cadiff Kirk J. Rudell December 8, 1998
While everyone prepares for the office costume party, Stuart tries to fake an affair with Nikki in order to break up with Deidre.
60 12 "Monkey Business" Andy Cadiff Stephen Godchaux December 15, 1998
Mike is challenged by the intelligence of the city zoo's new Chimpanzee.
61 13 "Taxi Driver" Andy Cadiff Tim Hobert January 5, 1999
Faced with a taxi driver's strike, Mike impersonates a cabbie in order to make a play on Nikki, by driving her boyfriend to the airport.
62 14 "The Nutty Deputy Mayor" Andy Cadiff Brian Buckner & Sebastian Jones January 12, 1999
Mike agrees to use a fat suit for a day to appease the overweight community.
63 15 "Not in the Line of Fire" Carl Lauten Michelle Nader & Amy Cohen January 26, 1999
The mayor doubts his Deputy Mayor's loyalty, when news footage shows Mike fleeing during an assassination attempt.
64 16 "Internal Affairs" Andy Cadiff Gayle Abrams February 9, 1999
Nikki is arrested for prostitution during a tryst with Mike.
65 17 "Dick Clark's Rockin' Make-Out Party '99" Andy Cadiff Tom Hertz February 16, 1999
Stuart breaks up with Deidre, who sues him for sexual harassment in revenge. Can Mike save his friend from losing his job, or is he next?. Stacey's aunt (Priscilla Presley) takes a liking to James.
66 18 "Back to the Future IV: Judgment Day" Andy Cadiff David S. Rosenthal February 23, 1999
Christopher Lloyd guest-stars as Mike Flaherty's political mentor from years past. Lloyd and Fox make several joking references to the Back to the Future trilogy films they starred in.
67 19 "Politically Incorrect" Andy Cadiff David Ronn & Jay Scherick March 2, 1999
The Mayor appears on Politically Incorrect and reveals that he is dating his secretary. Carter dates a boxer afraid to come out of the closet. Guest star: Bill Maher
68 20 "That's Entertainment" Andy Cadiff Tim Hobert & Gayle Abrams March 16, 1999
Forced to work on Oscar Sunday, the staff have movie themed flashbacks. (Clip show)
69 21 "The Last Temptation of Mike" Andy Cadiff J.O.S. Hartung & Clayton Hamilton April 6, 1999
Mike agrees to be Paul and Claudia's sperm donor. The Mayor keeps bothering James while he writes an article for Sassy Magazine.
70 22 "Carter & Stuart & Bennett & Deirdre" Andy Cadiff Mike Royce April 13, 1999
Carter and Stuart become friends with each others ex's in order to get back at each other. A temp at City Hall thinks Mike is in love with her.
71 23 "The Mayor With Two Brains" Andy Cadiff Stephen Godchaux & Kirk J. Rudell May 4, 1999
When a reporter gives Carter the limelight in an article meant to be about the Deputy Mayor, Mike becomes jealous.
72 24 "Wall Street" Andy Cadiff Philip Wen & Bill Callahan May 11, 1999
Mike helps James invest his life savings. The mayor gets his own action figure. Guest star: Jon Stewart
73 25 Klumageddon (Part 1) Andy Cadiff Kirk J. Rudell May 18, 1999
When The Mayor appoints Heidi Klum to work on an Animal Rights project with Mike, the supermodel tries to rekindle their previous relationship.
74 26 Klumageddon (Part 2) Andy Cadiff Bill Callahan & Philip Wen May 25, 1999
When Nikki overhears Mike agreeing to dump the Mayor for Janelle, she thinks he's breaking up with her. Stuart gives Carter's dog to Heidi Klum. (Last appearance of Stacey)

Season 4: 1999–2000[edit]

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Title Directed by Written by Original air date
75 1 "Catcher in the Bronx" Andy Cadiff Tom Hertz September 21, 1999
Mike tries to remember what happened between him and Heidi Klum the night before. Mike also has to find a Senate campaign manager for the mayor. Guest stars: James Carville, Roger Clemens (First appearance: Caitlin Moore (Heather Locklear))
76 2 "James and the Giant Speech" Andy Cadiff Stephen Godchaux September 28, 1999
Caitlin makes her presence known around City Hall by firing James as the speech writer and taking over Paul's office. The Mayor cheats at golf. Guest star: Nipsey Russell
77 3 "All the Mayor's Men" Andy Cadiff Jon Pollack October 5, 1999
Mike plans a break-in of the Mayor's office in order to find out what dirt Caitlin has on him.
78 4 "These Shoes Were Made for Cheatin'" Andy Cadiff Tad Quill October 12, 1999
Mike tricks Nikki into a couples therapy session. Stuart wants to join a gay gym.
79 5 "Rebel Without a Chair" Andy Cadiff Jay Scherick & David Ronn October 19, 1999
After being nominated for "Activist of the Year", Carter begins to feel unworthy of the award. Mike interrupts an interview, that results in a homosexual newspaper printing that he and the Mayor are an item.
80 6 "The Mayor May Not" Andy Cadiff Tom Hertz November 2, 1999
Bickering between Mike and Caitlin causes the Mayor to drop out of the Senate race. Paul and James wage a practical joke war against Stuart. Guest star: Al D'Amato.
81 7 "The Great Debate" Andy Cadiff Jill Cargerman November 9, 1999
After Caitlin bankrupts the Mayors Senate campaign, Mike woos a socialite (Amy Irving) to help raise funds. Nikki falls for an intern.
82 8 "How to Bury a Millionaire" Andy Cadiff Christopher Case November 16, 1999
During a rescue attempt of a baby trapped in a well, the Mayor falls down a rescue shaft. Paul appears on Who Wants To Be A Millionaire?. Guest star: Regis Philbin
83 9 "The Thanksgiving Show" Andy Cadiff Richard Day November 23, 1999
Paul thinks Caitlin is hitting on him. To not confuse a senator, Mike and Caitlin pretend that they are a couple and must share a room. Stuart and Deirdre are back together. Nikki and Janelle protect Sparky the turkey from James's evil clutches.
84 10 "The Doorman Always Rings Twice" Andy Cadiff Tim Hobert November 30, 1999
With the Mayor out of town campaigning, Mike becomes the interim mayor and sets off a citywide doorman strike. Paul opens a politically themed restaurant.
85 11 "Mustang Mikey" Carl Lauten Jay Scherick & David Ronn December 7, 1999
Mike and Caitlin go for a joyride in the Mayor's classic 1966 Ford Mustang and accidentally get it towed. James regains his speech writing duties and hires Deirdre to be Mike's new secretary.
86 12 "My Dinner with Caitlin (a.k.a. Christmas 1999)" Andy Cadiff Bill Callahan & Philip Wen December 21, 1999
Mike throws a Christmas party and invites Caitlin, then cancels the party so he can be alone with her. When she shows up with her own date, Mike has to get some guests.
87 13 "A Tale of Two Sisters" Andy Cadiff Jon Pollack January 12, 2000
Challenged to find a way to get over his crush on Caitlin, Mike makes a date with another woman: Caitlin's sister (Christine Taylor)
88 14 "Casino" Andy Cadiff Tim Hobert February 2, 2000
After a raffle snafu messed up by Paul, Mike must come up with $500,000, so he takes Paul to Atlantic City to count cards. Stuart and Carter blackmail Caitlin.
89 15 "The Marry Caitlin Moore Show" John Fortenberry Tad Quill February 9, 2000
Mike needs to hire a director to film the Mayor's newest Senate commercial and ends up hiring Caitlin's ex-husband. After a nasty rash, Paul becomes addicted to using makeup. Guest stars: Star Jones, Joy Behar, Lisa Ling, & Meredith Vieira
90 16 "Suffragette City" Andy Cadiff Tom Hertz February 16, 2000
Caitlin's rekindled relationship with her ex-husband drives Mike crazy. Carter enlists Stuart to help him bust a discriminating landlord by posing as a couple.
91 17 "Mike's Best Friend's Boyfriend" Andy Cadiff Dawn Urbont February 23, 2000
Mike thinks Carter's boyfriend is hitting on him.
92 18 "The Pig Whisperer" Andy Cadiff Jay Scherick & David Ronn March 8, 2000
Mike enlists James' help to evict a squatting Tomato farmer, by forcing him to enter a pig contest.
93 19 "Uneasy Rider" Andy Cadiff Tim Hobert & Jon Pollack March 22, 2000
The Mayor's father dies and Mike urges him to get in touch with his feelings. James thinks that Caitlin is attracted to him. Carter is upset that the office staff are using Paul's "Magic 8 Ball" instead of him for advice.
94 20 "About Last Night" David S. Rosenthal Tad Quill April 19, 2000
Preparing for a visit by the President, members of the staff deemed "Non-vital personnel" drown their sorrows at the local bar. Paul schemes to get his picture taken with the President.
95 21 "Don't Get on the Bus" Andy Cadiff Philip Wen & Bill Callahan April 26, 2000
Upon learning that Caitlin and her ex are getting re-married, Mike hits him with the Mayor's tour bus. Paul and James try to look like Carter in attempt to be treated smarter around the office.
96 22 "Airplane!" Andy Cadiff Jay Scherick & David Ronn May 3, 2000
Mike tries to win over Caitlin during a flight to San Francisco. The Mayor tries to change a light bulb in his office. Guest star: Patrick Ewing.
97 23 "An American Deputy Mayor in Paris" Andy Cadiff Bill Callahan & Philip Wen May 10, 2000
Mike flies to Paris to stop Caitlin from getting re-married.
98 24 "The Commitments" Andy Cadiff Jill Cargerman May 17, 2000
To show Caitlin that their relationship is more than physical, Mike abstains from sex for a week.
99 25 Goodbye (Part 1) Andy Cadiff Sarah Dunn May 24, 2000
City Hall is threatened by a reporter to reveal that the Mayor has mob connections. Guest star: Michael Gross as Mike's therapist.
100 26 Goodbye (Part 2) Andy Cadiff Bill Lawrence May 24, 2000
Mike fires himself to save everybody else. Mike says goodbye to the mayor and the staff and walks out of City Hall for the last time until a brief return in season 6. (Last appearances of James, Nikki, and Janelle)

Season 5: 2000–2001[edit]

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Title Directed by Written by Original air date
101 1 "Hello Charlie" Ted Wass Tom Hertz October 18, 2000
Charlie Crawford spends his first day in office as New York City's Deputy Mayor. The Mayor has trouble adjusting to office life without Mike. First appearance: Charlie Sheen as Charlie Crawford.
102 2 "Smile" Ted Wass Chris Henchy October 25, 2000
The mayor's dentist dies in the middle of a procedure. Carter and Stuart deal with a bike messenger who keeps stealing their parking spot
103 3 "The Spanish Prisoner" Ted Wass Bill Callahan & Phillip Wen November 1, 2000
The media finds out that Charlie is taking a Spanish course, thanks to Caitlin's meddling. Meanwhile Paul and the mayor decide that the office needs some more water cooler-talk. (First appearance of Angie)
104 4 "The Bone Collectors" Ted Wass Jon Pollack & Tim Hobert November 8, 2000
Stuart and Paul are put in charge of an archaeological dig. The mayor takes a much needed vacation.
105 5 "Blind Faith" Ted Wass Michelle Nader November 15, 2000
Charlie's advice prompts Claudia to become a nun.
106 6 "Balloons over Broadway" Ted Wass Tad Quill November 22, 2000
Paul convinces his mother that he is dating Caitlin, so she won't be upset that Claudia left him. Charlie tries to prove to Caitlin that his girlfriend isn't dumb. A quickly made balloon for the Thanksgiving parade goes awry in New York.
107 7 "Lost and Found" Ted Wass Bonnie Schneider & Hadley Davis November 29, 2000
Caitlin and Charlie fight for the attention of Caitlin's new friend. Carter, Stuart and Paul compete for a trip to New Orleans with the mayor.
108 8 "All the Wrong Moves" Ted Wass Stacy Traub December 6, 2000
An overworked Charlie causes problems after beating the mayor at racquetball. Paul's annual request for a raise is approved by the mayor after his loss of self esteem. Stuart hires an actor to go out with Carter.
109 9 "The Burgers of Wrath" Ted Wass Mark Torgove & Paul A. Kaplan December 13, 2000
Carter's behavior at a press conference results in the Mayor working a shift at a fast food restaurant. Stuart tries to impress the new secretary by posing as a biker.
110 10 "Toy Story" Ted Wass Chris Henchy December 20, 2000
Paul struggles to find the best joke for the mayor's Christmas card. Carter convinces Caitlin to volunteer with him at a retirement community. The mayor's attempt to be more involved in the office process goes awry.
111 11 "The Perfect Dorm" Ted Wass Jon Pollack & Tim Hobert January 10, 2001
Paul has to find a new place to stay after his ex-wife kicks him out, so he moves into a dorm.
112 12 "Hey Judith" Ted Wass Paul A. Kaplan & Mark Torgove January 17, 2001
The Mayor's new girlfriend clashes with Charlie over who should write an upcoming speech. Stuart is selected by ESPN to win a million dollars in a hockey contest. Guest star: Barry Melrose.
113 13 "The Gambler" Ted Wass Bill Callahan & Philip Wen January 24, 2001
The guys invite Charlie to play poker. Caitlin helps the Mayor become more self sufficient.
114 14 "In the Company of Dudes" Ted Wass Michelle Nader February 7, 2001
When the Mayor is named in a lawsuit, Charlie hires an old college buddy (Jason Priestley) to defend him. Paul and Stuart compete to win the affections of a new worker.
115 15 "The Image Maker" Ted Wass Bill Callahan & Philip Wen February 14, 2001
Caitlin hires an image consultant to make over the Mayor. A woman from Stuart's past comes back to haunt him. Guest star: Rosie O'Donnell
116 16 "Trainstopping" Ted Wass Jon Pollack & Tim Hobert February 21, 2001
When the Mayor takes a ride on the NYC Subway to prove its safety and efficiency, it breaks down, making Charlie late for an important date.
117 17 "Rain on My Charades" Ted Wass Peter Schneider February 28, 2001
Charlie realizes that he is ready for a committed relationship.
118 18 "You've Got Male" Ted Wass Mark Torgove & Paul A. Kaplan April 25, 2001
Caitlin and Charlie compete for an important account. The Mayor is criticized for not being more sensitive to women's issues.
119 19 "Minor League" Ted Wass Bill Callahan & Philip Wen May 2, 2001
Charlie tries out for a minor league team. The Mayor receives a death threat in the mail from an unlikely source. (Special guest voice: Bob Costas)
120 20 "Science Friction" Ted Wass Reese Bryant May 9, 2001
The media's reaction to the Mayor's ex-wife's tell-all book leads to humiliation and a boycott of the press. Caitlin dates a philanthropist (Scott Wolf) who's really into science fiction. Guest star: Roy Firestone.
121 21 "Brotherly Love" Ted Wass Bonnie Schneider & Hadley Davis May 16, 2001
Charlie attempts to interfere with Caitlin and Tim's burgeoning relationship. Meanwhile, Carter hires his sister to work at City Hall and will go to any length to avoid people discovering their connection.
122 22 A Shot in the Dark (Part 1) Ted Wass Paul A. Kaplan & Mark Torgove May 23, 2001
While on a police drive along, Charlie is shot. Carter and Stuart's friendship is seen in a different light.
123 23 A Shot in the Dark (Part 2) Ted Wass Tim Hobert, Jon Pollack May 23, 2001
Charlie dates a mentally unstable woman (Vanessa Marcil) to save face in front of Caitlin and her new boyfriend.

Season 6: 2001–2002[edit]

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Title Directed by Written by Original air date
124 1 "The Arrival" Ted Wass Tom Hertz September 25, 2001
The mayor begins a relationship with a judge (Farrah Fawcett) whose divorce is not finalized. Charlie confronts his feelings for Caitlin, but must take a backseat when Mike returns.
125 2 "A Tree Falls in Manhattan" Ted Wass Jon Pollack September 25, 2001
Wanting to impress his new girlfriend, the Mayor accidentally chops down a historical landmark tree that was planted by George Washington. Charlie becomes involved with Jennifer Duncan (Denise Richards), who is a rival opponent's Campaign Manager. (First Appearance: Tom Amandes as Julian Wheeler)
126 3 "Wife with Mikey" Ted Wass Tim Hobert October 2, 2001
Mike returns to City Hall to work on the Mayor's re-election campaign and to break-up with his fianceé (Olivia d'Abo). (Last appearance of Mike)
127 4 "The Apartment" Ted Wass Michelle Nader October 9, 2001
As polls show that the public disapproves of the Mayor's relationship with a married woman, Charlie finds his apartment being used as a secret hideaway. Caitlin asks Carter to go to a baby shower with her.
128 5 "Yet Another Stakeout" Ted Wass Chris Henchy October 16, 2001
Wheeler begins a smear campaign on the Mayor. Stuart begins a relationship with the love of his life (Lori Loughlin), but objects to her being a surrogate for Carter.
129 6 "Yeah Baby!" Ted Wass Bill Callahan & Philip Wen October 23, 2001
Carter's surrogate announces that she's pregnant and that the baby might be Stuarts. The Mayor hires a psychic political advisor (Queen Latifah).
130 7 "Sleeping with the Enemy" Ted Wass Mark Torgrove & Paul A. Kaplan November 6, 2001
Charlie's continued relationship with Wheeler's campaign manager results in the Mayor having to reveal a secret to the press. Paul asks Caitlin to help him woo a member of the Winston campaign.
131 8 "She's Gotta Habit" Ted Wass Stacy Traub November 6, 2001
After Jennifer admits to having a lesbian affair, Charlie fears she's falling for Caitlin. Paul arranges for the Mayor's girlfriend to arbitrate his divorce settlement.
132 9 "The Wedding Scammer" Ted Wass Bonnie Schneider & Hadley Davis November 13, 2001
Caitlin's mother (Michelle Phillips) arrives in New York for a family wedding. Paul and Stuart go to a Victoria's Secret fashion show. (Guest Star: Rhea Durham)
133 10 "Fight Flub" Ted Wass Mark Torgrove & Paul A. Kaplan November 20, 2001
After Wheeler suffers a heart attack, his wife (Elizabeth Mitchell) runs for mayor in his place.
134 11 "Chinatown" Ted Wass Bill Callahan & Philip Wen November 27, 2001
On Election Day, the Mayor proposes to Claire and Charlie and Jennifer make a decision on the future of their relationship.
135 12 "An Office and a Gentleman" Ted Wass Tim Hobert December 11, 2001
Charlie evaluates the staff to determine who is more worthy of a new office. Caitlin agrees to go on a date with a City Hall Santa who refuses to remove his costume.
136 13 "O Mother, Where Art Thou?" Ted Wass Jon Pollack January 8, 2002
Carter sets the Mayor up with a woman (Judith Light) who has a very personal history with the Winston Family. Caitlin and Charlie date a father and his daughter and end up in a family therapy session with them.(First Appearance: Tom (Perry King)).
137 14 "Rags to Riches" Ted Wass Mark Torgrove & Paul A. Kaplan March 5, 2002
Caitlin invites Charlie's father (Martin Sheen) to attend a surprise birthday dinner. Paul tries to help Carter mourn the death of Rags.
138 15 "Sex, Lies and Video Date" Ted Wass Michelle Nader March 12, 2002
The Mayor warns Charlie not to pursue his niece (Amy Jo Johnson). Paul appears on Blind Date. Guest Star: Roger Lodge.
139 16 "Eyes Wide Open" Ted Wass Chris Henchy March 19, 2002
Called away to an important meeting, Carter asks Charlie to watch over a sixteen year-old boy (John Francis Daley) he is mentoring. The Mayor has trouble sleeping.
140 17 "Age Against the Machine" Ted Wass Hugh Webber March 26, 2002
Charlie starts to feel his age after nights of endless partying with a younger girl and her friends. Carter asks Stuart to be his wingman at a Gay fundraiser.
141 18 "An Affair Not to Remember" Ted Wass Bill Callahan & Philip Wen April 9, 2002
While the Mayor acts as a Celebrity bartender, Caitlin reflects on her first love and realizes Charlie is to blame for losing him.
142 19 "Let's Give Them Something to Talk About" Ted Wass Stacy Traub April 16, 2002
Charlie tries to fulfill Caitlin's fantasies. Paul appears on a controversial radio talk show. (Guest Star: Larry Elder)
143 20 "Look Who's Not Talking" Ted Wass Hadley Davis & Bonnie Schneider April 23, 2002
Caitlin ends her relationship with Tom and tells Charlie she's interested in dating him. When they go out on their first date, things are awkward... until they end up in bed together, that is. But are they ready for a real relationship? Meanwhile, the Mayor hires a temp, Pete, to fill in for Stuart while he's out, but Paul and Carter see him as a threat.
144 21 "A Tale of Four Cities" Ted Wass Reese Bryant April 30, 2002
Unhappy with how Charlie interacts with an old flame, Caitlin tries to make Charlie jealous by showing interest in a reporter. The Mayors of New York and Los Angeles (Robert Hays) compete to make Paris their sister city.
145 22 "A Friend in Need" Ted Wass Tom Hertz & Bill Lawrence April 30, 2002
Surveillance footage shows Charlie and Caitlin having sex in the Mayor's office. Carter finally gets a foster child, that won't stop crying unless it's held by Paul.

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