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.

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.

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.

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.

The Mayor feels responsible for the death of his predecessor. Mike and Ashley try to avoid their new neighbors.

The Mayor's low approval ratings sink even lower when the Winston Administration supports a nominee with a checkered past.

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.

Mike asks a powerful land developer (George Wendt) for a favor. As the Winston Administration celebrates a reduction in crime rates, Paul gets mugged.

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.

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.)

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.

When the Mayor comes down with a cold, Mike must debate Ashley on a political talk show.
Last appearance of Ashley.

Mike breaks up with Ashley. Paul sets a New Year's resolution to be less gullible.

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.

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.

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).

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.

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.

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.

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.

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.

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.

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.

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).

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.

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).

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.

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))

While jogging, Carter is mistaken for a mugger and arrested in Central Park. Paul is afraid he's a racist.

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)

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.

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.

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.

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)

The Mayor's daughter (Alyssa Milano) participates in an animal rights protest to get back at him. Paul arranges to meet his pen pal.

The Mayor accidentally tells a little boy that there is no Santa Claus. James receives a care package from his parents.

Note: In 1999, TV Guide ranked this episode # 46 on its "The 50 Funniest TV Moments of All Time" list.^[37]

The staff all have trouble remembering what happened at the Mayor's New Year's Eve Party.

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)

The Mayor comes under fire for his membership in a club that doesn't allow women. Mos Def guest stars.

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.

Paul decides to propose to Claudia. Laurie returns in hopes of restarting her relationship with Mike.

Mike announces that he and Laurie are engaged. Paul gets cold feet about asking Claudia to marry him.

The staff are required to take drug tests. The Mayor breaks a Native American artifact before it can be donated to a museum.

After the Pope visits City Hall, the Mayor tries to be more holy and Mike feels guilty for his sinful ways in City Hall.

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.

Mike dates an insane magician, and then has trouble ending their relationship. Stuart and Carter open a gay bar.

Financial troubles cause Stuart and Carter to become roommates.

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.

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.

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.

Mike must keep his relationship with Heidi Klum a secret. Paul creates an incident involving a fan and ashes.

Mike is handling a political donor in the hope of receiving a donation. Stuart has been named as Stacey's boss for the day. Guest star: Barry Corbin

Mike considers adopting an abandoned baby. Cameo appearances by Mike's former girlfriends.

Mike tries to improve the Mayor's macho image. Stuart's girlfriend takes over Carter's apartment. (First appearance: Deidre (Beth Littleford))

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

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.

The mayor makes a promise to give a 14-year-old boy (Frankie Muniz) his kidney. Guest stars: Jeff Gordon and Jayson Williams.

The mayor hosts a televised Thanksgiving dinner. Stacey has a startling moment with Stuart.

While everyone prepares for the office costume party, Stuart tries to fake an affair with Nikki in order to break up with Deidre.

Mike is challenged by the intelligence of the city zoo's new Chimpanzee.

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.

Mike agrees to use a fat suit for a day to appease the overweight community.

The mayor doubts his Deputy Mayor's loyalty, when news footage shows Mike fleeing during an assassination attempt.

Nikki is arrested for prostitution during a tryst with Mike.

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^[66]) takes a liking to James.

Christopher Lloyd^[69] 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.

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

Forced to work on Oscar Sunday, the staff have movie themed flashbacks. (Clip show)

Mike agrees to be Paul and Claudia's sperm donor. The Mayor keeps bothering James while he writes an article for Sassy Magazine.

Carter and Stuart become friends with each other's ex's in order to get back at each other. A temp at City Hall (subbing for Stacey, who is not seen in this episode) thinks Mike is in love with her.

When a reporter gives Carter the limelight in an article meant to be about the Deputy Mayor, Mike becomes jealous.

Mike helps James invest his life savings. The mayor gets his own action figure. Guest star: Jon Stewart

When The Mayor appoints Heidi Klum to work on an Animal Rights project with Mike, the supermodel tries to rekindle their previous relationship.

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)

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))

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

Mike plans a break-in of the Mayor's office in order to find out what dirt Caitlin has on him.

Mike tricks Nikki into a couples therapy session. Stuart wants to join a gay gym. The mayor tries to pass an eighth grade quiz.

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.

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.

After Caitlin bankrupts the Mayors Senate campaign, Mike woos a socialite (Amy Irving) to help raise funds. Nikki falls for an intern.

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

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.

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.

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.

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.

Challenged to find a way to get over his crush on Caitlin, Mike makes a date with another woman: Caitlin's sister (Christine Taylor)

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.

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

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.

Mike thinks Carter's boyfriend is hitting on him.

Mike enlists James' help to evict a squatting Tomato farmer, by forcing him to enter a pig contest.

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.

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.

Upon learning that Caitlin and her ex are getting remarried, 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.

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.

Mike flies to Paris to stop Caitlin from getting remarried.

To show Caitlin that their relationship is more than physical, Mike abstains from sex for a week.

City Hall is threatened by a reporter to reveal that the Mayor has mob connections. Guest star: Michael Gross as Mike's therapist.

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)

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.

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

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)

Stuart and Paul are put in charge of an archaeological dig. The mayor takes a much needed vacation.

Charlie's advice prompts Claudia to become a nun.

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.

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.

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.

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.

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.

Paul has to find a new place to stay after his ex-wife kicks him out, so he moves into a dorm.

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.

The guys invite Charlie to play poker. Caitlin helps the Mayor become more self sufficient.

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.

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

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.

Charlie realizes that he is ready for a committed relationship.

Caitlin and Charlie compete for an important account. The Mayor is criticized for not being more sensitive to women's issues.

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)

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.

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.

While on a police drive along, Charlie is shot. Carter and Stuart's friendship is seen in a different light.

Charlie dates a mentally unstable woman (Vanessa Marcil) to save face in front of Caitlin and her new boyfriend.

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.

• The episode originally was supposed to air on September 11th, but was delayed for two weeks until the 25th due to the terrorist attacks that occurred in NYC earlier on that day.

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 an opponent's Campaign Manager. (First Appearance: Tom Amandes as Julian Wheeler)

Mike returns to City Hall to work on the Mayor's re-election campaign and to break-up with his fiancée (Olivia d'Abo), only to change his mind and marry her instead. (Last appearance of Mike)

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. Note that this episode uses the same title as episode 3 of season 1, but otherwise has no direct connection to that episode.

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.

Carter's surrogate announces that she's pregnant and that the baby might be Stuarts. The Mayor hires a psychic political advisor (Queen Latifah).

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.

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.

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)

After Wheeler suffers a heart attack, his wife (Elizabeth Mitchell) runs for mayor in his place.

On Election Day, the Mayor proposes to Claire and Charlie and Jennifer make a decision on the future of their relationship.

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.

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)).

Caitlin invites Charlie's father (Martin Sheen) to attend a surprise birthday dinner. Paul tries to help Carter mourn the death of Rags.

Absent: Alan Ruck as Stuart Bondek

The Mayor warns Charlie not to pursue his niece (Amy Jo Johnson). Paul appears on Blind Date. Guest Star: Roger Lodge.

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.

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.

While the Mayor acts as a Celebrity bartender, Caitlin reflects on her first love and realizes Charlie is to blame for losing him.

Absent: Alan Ruck as Stuart Bondek

Charlie tries to fulfill Caitlin's fantasies. Paul appears on a controversial radio talk show. (Guest Star: Larry Elder)

Absent: Alan Ruck as Stuart Bondek

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.

Absent: Alan Ruck as Stuart Bondek

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.

Absent: Alan Ruck as Stuart Bondek

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.