The Mayor is a fictional character portrayed by Barry Bostwick in the TV series Spin City.
In the first episode they appeared in, titled Pilot (season 1), they were 51 years old.
They appear in all 145 aired episodes and have accumulated 292 positive votes.
The character of The Mayor is mainly associated with Mike Flaherty, Paul Lassiter and Caitlin Moore.
Episodes145
Pilot
episode S1.E1 september 1996Mike Flaherty has to juggle the interests of his conservative mayor boss and a gay activist whom the Mayor has unwittingly insulted. At home, Mike has to deal with his reporter girlfriend Ashley, when it finally dawns on him that she doesn't just sleep over but that she actually lives with him. To appease both Carter, by having his voice heard, and the mayor, by correcting his gaffe, Mike hires Carter as his new consultant of minority affairs.
The Great Pretender
episode S1.E2 september 1996The mayor's vocal wife causes Mike and the staff heartache as Winston and the staffers attend a dinner hosted by Catholic and Jewish leaders in New York City at which the mayor is being honored. Meanwhile, Paul is uptight over Ashley's latest reporting hot streak involving an internal audit at a Queens high school and Mike faces problems with his love life following his being named the Sexiest Man in New York.
The Apartment
episode S1.E3 october 1996Mike and Ashley's hectic schedules cause problems in their personal lives at home. Meanwhile, the garbage strike continues and as negotiations continue between the Mayor and the workers, Stuart is left in charge of the office while Mike keeps Winston in line.
Pride and Prejudice
episode S1.E4 october 1996A camera crew for a magazine films Mike and his staff performing their daily office duties and they each give their own spin on what goes on in City Hall every day. While this is going on, the reporter develops the hots for awkward speech writer James and Carter encourages the mayor to address the pressing issue of AIDS in New York City.
The Rivals
episode S1.E5 october 1996Winston, jealous of the old Mayor Garfield's likability factor which he just can't seem to obtain, wishes death on the man and within a couple of days, he gets his wish! Mike and the staff try to console the Mayor by telling him it's not his fault and that Garfield had a bad heart. Nikki bets that none of the men in the office have what it takes to be a dad.
A Star Is Born
episode S1.E6 october 1996Dr. Bronsteen, an old professor of James', is appointed the city's new School Commissioner by Winston, but it is later revealed by the press that he was caught on camera smoking pot at a 1971 Grateful Dead concert causing duress for Mike and disbelief for James. Ashley is offered a job reporting for a local TV station.
Grand Illusion
episode S1.E7 october 1996Ashley's job for New York's ABC affiliate isn't as fulfilling as her old one; Carter plans to marry Nikki to make a point to the Mayor on gay marriage. He believes that if two heterosexual people are allowed to marry no matter how close they are or how much they have in common, gays should be able to have the same luxury.
The High and the Mighty
episode S1.E8 november 1996Paul's identity is stolen during a period where crime in the city is at its lowest rate in years. A famous developer signs onto a project for the Mayor's office and hopes for something in return: he suggests an unethical opportunity for Mike to inform the billionaire about the lowest bid for a construction contract he wants.
Meet Tommy Dugan
episode S1.E9 november 1996A childlike janitor wins the Mayor For A Day contest intended for kids only and begins to have more influence over the press than the Mayor himself, who isn't particularly favored by the press.
The Competition
episode S1.E10 november 1996City Council's Lisa challenges Mike to a turkey cook-off on Thanksgiving to see who can feed more homeless people: the Mayor's office or City Council. Meanwhile, James looks for a way to break up with his girlfriend of seven years. To complicate things, Becky shows up to surprise her long-distance boyfriend for the holiday.
Dog Day Afternoon
episode S1.E11 december 1996Mike attempts to appease the Police Commissioner by honoring a fallen hero: Bingo, the police dog. Things get out of hand, however, when Paul and Carter lose the dog's body after they're kicked out of a cab and Mike can't stall the service for Bingo any longer. Ashley ponders boundary issues when she overhears a message intended for Mike regarding the Bingo situation.
Criss Cross
episode S1.E12 december 1996When the Mayor falls ill due to Paul spreading a nasty flu bug all around the office, Mike steps in for His Honor on the national TV show "Counterpoint." The best part is that his opponent happens to be his girlfriend, Ashley. Also, Carter has the staff coming to him for ridiculous dating and relationship advice. At the end, he thanks God that he's gay.
Bye Bye Love
episode S1.E13 january 1997After Ashley Schaeffer leaves him for a better job in Los Angeles, Mike attempts to cover up by saying it was a mutual decision and that he gave her his approval to take the job. Mike later reaches his breaking point as he nearly strangles Stuart in a restaurant after he calls her a bitch and confesses to Nikki that he begged her to stay but she left anyway.
Starting Over
episode S1.E14 january 1997New Asst D.A. Danielle Brinkman, an old friend of Mike's, is eager to get re-acquainted, but out-of-sorts Mike finds it hard to date after his breakup with Ashley, despite her great looks & advances. Paul meets his fan club president.
Gabby's Song
episode S1.E15 january 1997Mike tries to charm hard-nosed new appointee Gabrielle Sanchez, by whom the men feel threatened. Claudia wants to get to know Paul intimately.
Kiss Me, Stupid
episode S1.E16 february 1997Valentine's Day brings romantic chaos: Carter's ex-boyfriend Spence comes to visit and has a surprise. James hits on Nikki. Paul and Claudia's liaison is a comedy of errors.
An Affair to Remember
episode S1.E17 february 1997Mike plans a star-studded party for the Mayor's 50th birthday, but tries to keep him away from Holly Cohen, Randall's romantic interest from the governor's office so that the Winston marriage doesn't suffer.
Snowbound
episode S1.E18 february 1997During a blizzard, an inept security guard pursues a nudist in City Hall; Mike's high school crush visits en route to Paris; Paul & Randall make gaffs during a radio broadcast; and Carter and Stuart get locked in the boiler room.
Striptease
episode S1.E19 march 1997At a constituent's bachelor party in a strip club, the staffers find that Mike's new girlfriend is a stripper, then must deal with bad publicity from reporters and photographers.
Deaf Becomes Her
episode S1.E20 march 1997Paul's leg injury, Mike's toothache, and possibly falsified resumes all get mixed up with accidental insults to the hearing-impaired community.
Hot in the City
episode S1.E21 april 1997Mike's aggressive former girlfriend Carrie makes him uncomfortable by asking to have a child with him; a drop in the mayor's approval rating coincides with the reunion of rock musicians.
Bone Free
episode S1.E22 april 1997Randall's secret fantasies about a speaker lead the public to believe that he has a heart condition. Is Nikki's new boyfriend George really writing a screenplay or just taking advantage of her?
The Mayor Who Came to Dinner
episode S1.E23 may 1997James helps Stuart write a speech for his condo association meeting; Nikki models in a charity fashion show; Randall breaks up with his wife after 22 years and moves in with Mike.
Mayor Over Miami
episode S1.E24 may 1997Randall is depressed after signing divorce papers. Claudia pursues Paul. So both men skip town for Miami, leaving the other staffers to cover for them. Stuart has a personality change due to his new girlfriend.
Paul Flew Over the Cuckoo's Nest
episode S2.E1 september 1997Claudia has trust issues, and the press questions Paul's sanity, after his impulsive trip to Florida. Mike handles Randall's divorce and falls for the opposing lawyer. Carter spies on neighbors and is accused of heterophobia.
Porn in the U.S.A.
episode S2.E2 october 1997Randall is caught on camera while visiting an X-rated video store to research a crusade against porn on public access TV. Paul's visiting mother Abby turns out to be a hottie. Nikki bonds with Mike's new girlfriend Laurie.
Wonder Woman
episode S2.E3 october 1997Mike's new girlfriend Laurie wants no commitment. Janelle applies for a raise. Stuart and Carter try to find out what James' new hobby is.
The Goodbye Girl
episode S2.E4 october 1997Mike discourages Randall from pursuing a young woman two weeks after his divorce, for fear of a media frenzy. With Janelle's promotion to Randall's personal assistant, Mike needs a new one and Stacey Paterno applies for the job.
In the Heat of the Day
episode S2.E5 october 1997Carter goes jogging to plug Randall's fitness program but gets mistaken for a mugger and publicizes the arrest to soothe his outrage. Paul accidentally insults a Mexican councilman. Stacey and Nikki coach James on wooing the supply girl.
Radio Daze
episode S2.E6 october 1997Mike and Randall clash repeatedly with an obnoxious deejay. Paul tries to write an objective critique of Randall's autobiography. The female staffers fantasize about the handsome man who delivers bottled water to the building.
The Thirty Year Itch
episode S2.E7 november 1997Everyone struggles to figure out what to give Mike for his 30th birthday, as he prepares to meet with a high school girlfriend atop the Empire State Building. Meanwhile, the mayor asks Carter to find out whether the mayor's nephew Stephen is gay.
My Life Is a Soap Opera
episode S2.E8 november 1997Mike dates Lisa, a writer for "All My Children", then sees details of their romance played out on episodes of the show. A newspaper photo's caption names Stuart as Carter's boyfriend, so Stuart uses the ruse to get dates.
Family Affair
episode S2.E9 november 1997Winston is accused of paying a call girl, and Mike sets out to prove it false. But Winston was with Mike's visiting mother at the time. Nikki dates a shy ventriloquist. A panicky security guard shoots Paul by mistake.
Family Affair: Part 2
episode S2.E10 november 1997Mike's mom can save Randall from scandal by revealing their tryst. Carter's planned trip to the Bahamas goes awry when co-workers want to join him. Paul hires Stacy to represent him when he faces off against Hank on The People's Court.
They Shoot Horses, Don't They?
episode S2.E11 december 1997James is asked to chaperon Randall's visiting free-spirited daughter Meg, who disrupts an animal rights rally. Paul corresponds with a pen pal.
Miracle Near 34th Street
episode S2.E12 december 1997Randall accidentally tells the public that there is no Santa Claus, and sets off a chain of mishaps during the Christmas season.
Same Time Next Year
episode S2.E13 january 1998Randall hosts a New Year's party, where Nikki's boyfriend dumps her for the catering girl, Carter helps Stuart grieve over a deceased house pet, everyone suggests resolutions for each other, and several people drink way too much alcohol.
The Paul Lassiter Story
episode S2.E14 january 1998Randall has a tight deadline for writing a book but can expect no help from close-mouthed Mike, whose recent doctor visit hints that he may have cancer. And several staffers try to obtain new office chairs from a snooty supply technician.
Gentleman's Agreement
episode S2.E15 january 1998Mike tries to talk Mayor Winston out of joining a private club that prohibits women, but his efforts lead to both of them and several other staffers being trapped in the club steam room by a muckraking reporter. Meanwhile, Stuart tries to join the women's book club at the office and Paul tries to help when James is swindled by a local card shark.
Deaf Man Walking
episode S2.E16 february 1998Randall has hearing problems; Stuart gets a new office upstairs; Stacey wants to move out of the family household, so her grandmother blames Mike and puts a curse on him.
The Marrying Men
episode S2.E17 march 1998Paul chooses an engagement ring for Claudia, but Mike pays for it and keeps it until Paul can reimburse him. When Laurie finds the ring in Mike's pocket, she thinks Mike is proposing to her. Meanwhile, Stuart and Stacy go on a date.
One Wedding and a Funeral
episode S2.E18 march 1998Mike and Laurie plan their wedding with Randall as best man; Paul gets cold feet about marrying Claudia; Nikki is the first to fantasize about what it would be like being married to Mike.
A River Runs Through Me
episode S2.E19 march 1998As a preemptive strike against illegal drug use, Mike mandates that the staff will undergo mandatory drug testing, then accidentally ingests peyote during a visit with Native American constituents.
The Pope of Gracie Mansion
episode S2.E20 april 1998The Pope's visit to New York City inspires Randall to mix politics with religion; Paul's pet turtle goes missing; Nikki and Stacy both date Carter's friend Daniel; and Mike and Stuart work to avert an MTA strike.
Bye, Bye, Birdie
episode S2.E21 april 1998The staffers throw prenuptial parties for Paul and Claudia, but Stuart plays a prank on the women by changing the planned entertainment for Claudia's party; an offensive statue turns up on display in City Hall.
The Lady or the Tiger
episode S2.E22 may 1998Mike's clingy girlfriend Kaari is a magician who doesn't take kindly to his rejection; Stuart and Carter open their own bar; James loans money to Randall and then tries to get reimbursed.
Single White Male
episode S2.E23 may 1998Stuart wants to become Carter's new roommate so that both of them can have lower rent; animal lover James objects when Paul brings his cat to kill the rat that's on the loose in Mike's office.
The Paul Bearer
episode S2.E24 may 1998Paul and Claudia's wedding day is fraught with problems: Randall suddenly suffers from a speech impediment and best man Mike learns that the church is double-booked with a funeral.
Dead Dog Talking
episode S3.E1 september 1998Mike takes credit when someone else saves a baby from falling into the zoo's sea lion tank. Paul uses crutches to obtain undeserved sick leave but Stacy knows he's faking. Carter brings home a 19-year-old dog named Rags.
There's Something About Heidi
episode S3.E2 september 1998Mike's dates with Heidi Klum are tabloid fodder. Randall laughs at inappropriate moments because his father told him that crying is a sign of weakness. Nikki has a sex dream about Mike and tells it to Carter, who blabs it to Stuart.
Gone with the Wind
episode S3.E3 october 1998The care package that James gets from home contains a dead pet and Mike's relationship with Heidi leaves no time to help. Since Carter and Paul have no air conditioning, Carter springs for a large fan but Paul won't pay his share.
The Deer Hunter
episode S3.E4 october 1998Mike goes hunting with campaign contributor Peter Noland, who makes killing deer a prerequisite for his contribution. Acting deputy mayor Stuart drives Stacy nuts until Janelle intervenes. James subs for Paul, who wants a raise.
It Happened One Night
episode S3.E5 october 1998Mike may adopt an abandoned baby; his former flames dish on him. Randall needs to go to therapy but gets nervous and briefs James to go in his place.
Three Men and a Little Lady
episode S3.E6 october 1998While trying to help Randall improve his image, Mike, Randall, and Paul are mugged by a young woman. Stuart starts dating Deirdre West, who turns out to be just as loathsome as he is.
An Officer and a Gentleman
episode S3.E7 november 1998When an old friend of Mike's who's in the navy comes to town, he's happy to see him. Until he learns that he hooked up with Carter.
Quest for Fire
episode S3.E8 november 1998An Olympic torch-bearer from Nigeria gets lost in NYC, so workaholic Mike vacations at the office. Paul moves to Harlem and tries to assimilate by adopting black stereotypes. Nikki talks of a fictitious beau and Mike wants to meet him.
The Kidney's All Right
episode S3.E9 november 1998Randall accidentally volunteers to donate a kidney to a sick child; Paul avoids an aggressive reporter; Stacey stays with Carter and Stuart while her place is fumigated.
Gobble the Wonder Turkey Saves the Day
episode S3.E10 november 1998Randall's cranky father joins the staff for a live televised Thanksgiving dinner at the Mayor's mansion, where he and Randall argue, Carter and James stage a puppet show to promote family values, and Stuart tricks Stacey.
Local Hero
episode S3.E11 december 1998Mike plays matchmaker for Stacey and a timid city councilman, while everyone prepares to attend a costume party at which several staffers may perform.
Monkey Business
episode S3.E12 december 1998At Christmas time, Randall plays Santa Claus; Stuart and Carter meet an older gay couple who have moved into their building; and Mike tangles with an intelligent chimp named Bobo who was given to the Central Park Zoo as a gift.
Taxi Driver
episode S3.E13 january 1999Stacey dates a simpleton cab driver, while Randall & Mike negotiate with his labor union's temperamental representative. Stuart tricks Paul into dating while Claudia is out of town. Mike takes a drastic step to separate Arthur and Nikki.
The Nutty Deputy Mayor
episode S3.E14 january 1999Mike learns about weight discrimination when he dons a fat suit for a day, while James plans to beat him in a bachelor auction for charity. Stuart won't introduce his sister to the staff.
Not in the Line of Fire
episode S3.E15 january 1999After a false alarm shooting at a pier opening, paranoid Randall thinks Mike deserted him in a life-or-death situation, and then gives Mike the cold shoulder. Mike is obsessed with Nikki but can't have her because Arthur has proposed.
Internal Affairs
episode S3.E16 february 1999Nikki breaks up with Arthur and joins Mike for a hotel tryst, which goes awry when Mike wants to keep their relationship secret. Stacey plays a phone prank on Paul. Carter, James, and Stuart all go on a stakeout with Randall.
Dick Clark's Rockin' Make-Out Party '99
episode S3.E17 february 1999Stuart breaks up with Deidre, who files sexual harassment charges against him. Stacy's visiting aunt Marie hits on James. Randall starts a romance with a staff member.
Back to the Future IV - Judgment Day
episode S3.E18 february 1999Mike's political mentor comes to City Hall to help on the Millennium project, and displays a literal Messianic complex. Things heat up between Randall and Janelle. A mishap occurs when Paul dog-sits Rags as a favor to Carter.
Politically Incorrect
episode S3.E19 march 1999Randall says the wrong thing on a TV talk show. Paul is addicted to Stacy's meatball sandwiches. Carter dates closeted gay boxer Bennett Jones, who fights a match with Stuart.
That's Entertainment
episode S3.E20 march 1999The staffers try to finish work so they can watch the Academy Awards, and they pass the time by sharing their favorite movie moments.
The Last Temptation of Mike
episode S3.E21 april 1999Mike may help Paul and Claudia conceive a child. Doug, a City Hall tour guide, annoys the staffers, especially Stacey. James can't get peace and quiet in the office.
Carter & Stuart & Bennett & Deirdre
episode S3.E22 april 1999Stuart befriends Carter's ex-boyfriend Bennett, so Carter takes revenge by befriending Deidre. Subbing for absent Stacey, temp Gayle thinks Mike is coming on to her. James starts writing a City Hall newsletter.
The Mayor with Two Brains
episode S3.E23 may 1999A magazine cover story about Mike winds up focusing on Carter instead. James learns of Mike's affair with Nikki and struggles to keep it a secret, with unfortunate results to his physical appearance.
Wall Street
episode S3.E24 may 1999Mike and his stockbroker help James invest responsibly. Randall commissions an action figure that looks like him, in order to donate all the profits to charity.
Klumageddon: Part 1
episode S3.E25 may 1999Randall asks Heidi Klum to help with an animal rights campaign, but she comes between Mike and ailing Nikki. James objects to Randall adding humor to his press conferences.
Klumageddon: Part 2
episode S3.E26 may 1999Nikki thinks Mike is dumping her for Heidi Klum. Stuart gives Carter's dog to Heidi to elicit her sympathy. Paul and James compete to see who can give better massages to Stacey.
Catcher in the Bronx
episode S4.E1 september 1999Mike can't recall how he and Heidi Klum wound up in bed together. At the office, he must interview applicants to manage Randall's Senate campaign. Paul applies for a free life insurance policy but asks Stuart to take the physical for him.
James and the Giant Speech
episode S4.E2 september 1999James is under pressure to write a speech so that Caitlin doesn't take over his job and fire him. Paul sucks up to Caitlin, who tries to take his office away from him. Mike tries to re-establish communication with angry Nikki.
All the Mayor's Men
episode S4.E3 october 1999When Caitlin instigates background checks on the staff, Mike tries to one-up her by staging an internal break-in and stealing the files. Meanwhile, James tries to coach Mayor Winston for an upcoming appearance in an independent film.
These Shoes Were Made for Cheatin'
episode S4.E4 october 1999Mike tricks Nikki into attending couples counseling. Stuart visits Carter's gym for gay clients. Eighth graders challenge Randall to take a standardized test, and Paul winds up wearing a strange costume for a press conference.
Rebel Without a Chair
episode S4.E5 october 1999Mike accidentally convinces a magazine reporter that he and Randall are lovers. Paul fights the new restroom attendant. Carter is named Activist of the Year. Stuart brings a suggestive paperweight into the office.
The Mayor May Not
episode S4.E6 november 1999Tired of Stuart's pranks, Paul and James team up to fight back. Carter falls for a rich man whose principles he doesn't share. Randall ponders a run for Senator, and sends Mike and Caitlin to couples therapy to stop their bickering.
The Great Debate
episode S4.E7 november 1999Mike courts a wealthy NYC socialite to fund Randall's Senate campaign, which Caitlin bankrupted. Nikki and Janelle compete to mentor a hunky intern. Paul moves in with coworkers temporarily after a tiff with Claudia.
How to Bury a Millionaire
episode S4.E8 november 1999Paul is set to appear on "Who Wants to Be a Millionaire" and recruits the other staffers to help him in case he needs to "phone a friend." During a rescue operation to free a trapped baby, Mayor Winston falls into an adjacent pit and causes a media frenzy. Carter takes Rags to a day-care facility for canines. The city firefighters go on strike.
The Thanksgiving Show
episode S4.E9 november 1999Mike and Caitlin play a couple to win the endorsement of widowed Senator Grady during Thanksgiving at Randall's Connecticut home, while Nikki and Janelle try to keep James from killing a turkey for their holiday dinner.
The Doorman Always Rings Twice
episode S4.E10 november 1999Randall accidentally slights Mike during a press conference. Mike deals with angry reps from the doorman's union. Deidre meets Caitlin and begins to dress like her. Paul opens a politically-themed restaurant with James and Nikki helping.
Mustang Mikey
episode S4.E11 december 1999Mike and Caitlin borrow the Mayor's car for a joy ride. James hires Deidre to work in the office as Mike's personal assistant. Carter and Nikki bicker over photo ID's.
My Dinner with Caitlin
episode S4.E12 december 1999Caitlin misinterprets a private evening with Mike as a holiday party, and brings a date. Paul infiltrates Nikki's holiday clothing drive in order to mooch. James volunteers to work for a crisis hot line.
A Tale of Two Sisters
episode S4.E13 january 2000Caitlin tries to sabotage Mike's date with her visiting sister Catherine. Stuart joins the other staffers in taking an interest in art. Paul is upset to learn that Carter makes more money than Paul does, so Paul starts acting immaturely about the matter.
Casino
episode S4.E14 february 2000Paul's raffle ticket glitch results in dozens of winners. James gets braces at the same time that the new mail girl finds him attractive. Stuart and Carter blackmail Caitlin in order to get out of doing her busy work for her.
The Marry Caitlin Moore Show
episode S4.E15 february 2000In order to improve Mayor Winston's political advertisements, Mike hires a British director named Trevor who turns out to be more than just an old friend to Caitlin. James obsesses over whether or not he is gay. Paul uses makeup to cover a skin rash.
Suffragette City
episode S4.E16 february 2000Mike hires New York's oldest living voter, a 107-year-old woman, for a job. Caitlin's romance with Trevor upsets him. Paul muscles in on James' Hey Guy. Carter accuses a landlord of discriminating against gays.
Mike's Best Friend's Boyfriend
episode S4.E17 february 2000Carter's new boyfriend Alex may be coming on to Mike. Paul tries to impress a reporter from his hometown until Randall upstages him. A Good Samaritan contest brings out five finalists. Stu plays a fat neck gag on James.
The Pig Whisperer
episode S4.E18 march 2000Angry farmers fight Randall's land proposal, and their leader turns out to be an ex-rival of James, who may be able to save the day. Deidre had a fling with Paul years ago. Carter disapproves of Randall spending time with a rap singer.
Uneasy Rider
episode S4.E19 march 2000Randall seems unaffected by his cold father's death and rides an emotional roller coaster; Paul uses the opportunity to kiss up to him. Staffers use Paul's Magic 8 ball to make simple decisions. Is Caitlin attracted to James?
About Last Night
episode S4.E20 april 2000President Clinton pays a visit to City Hall, during which James helps Paul to obtain a photograph with the President. Nikki and Carter have a flirting contest.
Don't Get on the Bus
episode S4.E21 april 2000Romantic sparks fly between Mike and Caitlin during Mayor Winston's listening tour. Carter tells Nikkie to be more aggressive toward the men she wants in her life. James and Paul decide that Carter is more successful than they are, so they try to duplicate his success by emulating his physical characteristics.
Airplane!
episode S4.E22 may 2000Mike continues his pursuit of Caitlin, despite her engagement to remarry Trevor. Stuart disrupts Carter's hunger strike against an environmental polluter. Randall, Paul, and James try to do maintenance work in the office.
An American Deputy Mayor in Paris
episode S4.E23 may 2000Mike follows Caitlin to Paris in order to break up her engagement to Trevor. James preps Randall to receive an award that he may not have earned. Stuart asks Nikki to pose for a calendar so that he can donate proceeds to charity.
The Commitments
episode S4.E24 may 2000Mike abstains from sex for a week to prove that his feelings for Caitlin aren't just physical, and Caitlin doubts he can do it. Randall uses Carter's dog Rags to project an animal-friendly image to animal rights activists.
Goodbye: Part 1
episode S4.E25 may 2000Muckraking reporter Wayne Sheridan wants to connect Randall's administration to organized crime. Several staffers make this easy, including Randall and Nikki. Randall gives a sanitation contract to a mobster, whom Nikki is dating.
Goodbye: Part 2
episode S4.E26 may 2000When Sheridan goes public about the Winston administration's links to organized crime, Mike decides to take the fall and save everyone else. He submits his resignation, leading everyone to drown their sorrows and say their goodbyes.
Hello Charlie
episode S5.E1 october 2000Mike Flaherty's replacement Charlie Crawford reports to work. Caitlin's efforts to avert a toll booth workers' strike hit a roadblock when the woman with whom she's negotiating turns out to be an ex-girlfriend of Charlie's.
Smile
episode S5.E2 october 2000Randall needs dental work, but his long-time dentist drops dead during the procedure. Charlie interviews personal assistants until Caitlin hires one based on looks. Stuart goads Carter into aggression when Carter's parking space is stolen.
The Spanish Prisoner
episode S5.E3 november 2000Charlie never graduated school due to a missed Spanish final exam, and Caitlin does more harm than good in trying to help. Randall installs a water cooler. Stuart is jealous of Carter's friendship with Caitlin and uses Rags to get even.
The Bone Collectors
episode S5.E4 november 2000Caitlin makes an appearance on Regis Philbin's live television show. Mayor Winston takes a vacation - well, sort of. Paul and Stuart mediate a dispute between paleontologists and construction workers.
Blind Faith
episode S5.E5 november 2000An abrasive blind man finds Caitlin dull, spurns her, and causes her to try to improve her personality. In need of a religion refresher, Randall and Charlie accidentally wreak havoc on Claudia's religious education class and her future.
Balloons over Broadway
episode S5.E6 november 2000The staff tries to appease Native Americans by having an appropriate float in the Thanksgiving parade, but things go awry. Paul's visiting mother doesn't know that Claudia has left him and he is afraid to tell her.
Lost and Found
episode S5.E7 november 2000Charlie's one-night stand with Caitlin's yoga class buddy Samantha doesn't go the way he planned. Paul, Stuart, and Carter compete to join Randall on a trip to New Orleans.
All the Wrong Moves
episode S5.E8 december 2000Charlie plays racquetball with Mayor Winston, beats him in a match, and crushes his ego. Paul campaigns to get a raise. Stuart hires an actor to date Carter.
The Burgers of Wrath
episode S5.E9 december 2000Randall, Carter, and Charlie spend time working in a fast-food restaurant. Stuart tries to impress Angie by feigning expertise on motorcycling. Paul teaches Caitlin the rigors of celibacy.
Toy Story
episode S5.E10 december 2000Confiscated toys may become part of a photo op for Randall, who undermines Charlie's staff meetings. Carter persuades Caitlin to volunteer with him in a retirement home. Paul seeks jokes to enliven the City Hall holiday greeting card.
The Perfect Dorm
episode S5.E11 january 2001Paul moves into a college dorm. Charlie sets up Caitlin on a blind date with a bumbling optimist. Randall parks in a handicapped spot and makes amends by having a ramp installed in City Hall.
Hey Judith
episode S5.E12 january 2001Much to Charlie's disdain, Mayor Winston's new girlfriend Judith usurps Charlie's authority by involving herself in policy issues at City Hall. Carter and Stuart brawl during a hockey game.
The Gambler
episode S5.E13 january 2001Paul, Carter, and Stuart goad Charlie into playing poker with them, not knowing that he is a reformed gambler. Caitlin helps Randall search for a new housekeeper, then vetoes every applicant.
In the Company of Dudes
episode S5.E14 february 2001Charlie calls a college buddy to defend Randall in a lawsuit after he ruins a model's coiffure at a charity fashion show, but the man has eyes for Caitlin. Carter coaches Paul on wooing an attractive new hire before Stuart goes after her.
The Image Maker
episode S5.E15 february 2001Caitlin hires an image consultant to determine why Mayor Winston's approval rating with women has plummeted. Stuart's overbearing ex-wife comes back into his life, courtesy of Carter's bungled attempt at matchmaking.
Trainstopping
episode S5.E16 february 2001Charlie gets trapped in a stalled train before his date with a woman he's desperate to impress. Carter's weird neighbor Kurt hits on him, and Paul helps by getting Carter reservations at a posh restaurant.
Rain on My Charades
episode S5.E17 february 2001Randall's visiting daughter Meg decides to become a free spirit by dropping out of law school and moving south with her loser boyfriend. Charlie blows off a date with Julia to attend a sporting event with Stuart, Carter, and Paul.
You've Got Male
episode S5.E18 april 2001Caitlin and Charlie vie for an important account. Randall bonds with Paul during a father / son golf tournament. Carter helps Stuart write the script for a pornographic movie during working hours.
Minor League
episode S5.E19 may 2001Charlie fulfills a dream of playing minor league baseball, but Caitlin bribes the pitcher into going easy on him so he'll return to work. Randall receives a death threat and beefs up security, which Paul exploits to get revenge on Stuart.
Science Friction
episode S5.E20 may 2001When his wife's book turns out a great laugh, but at the expense of his male pride, mayor Winston gets so depressed he is unfit to appear in public and must be replaced by his top aids. Superrich most eligible bachelor Tim Connelly is very pleased he thus spends an evening with Caitlin, who is attracted to him, except his embarrassingly boyish obsession with a SciFi series, which even means their next date is a fan convention. Charlie has a ball getting mayoral attention. Stuart enjoys taunting his colleagues by helping stingy Paul steal Carter's nicotine chewing gum, so they'll both be tortured by its addictive properties.
Brotherly Love
episode S5.E21 may 2001Carter helps his sister get a job at City Hall, but lets Stuart and Paul think she is his lover. Randall thinks he looks like Charlton Heston. Charlie and Tim compete for Caitlin's affections.
A Shot in the Dark: Part 1
episode S5.E22 may 2001When Tim doesn't just propose another evening with Caitlin but a trip to St.Barts, she has her first real row with Charlie. After the press finds out the mayors limousine was carjacked with him, Paul and Charlie in it, PR demands they spend a night with an officer on patrol in a police car, while Stuart and Carter ride a police horse together; Charlie gets shot -accidentally as a video camera proves, but by...- which brings Caitlin running back to him, only to find out it's just a superficial wound...
A Shot in the Dark: Part 2
episode S5.E23 may 2001Caitlin finds that Charlie lied, and pulls a prank on him. Charlie dates a mentally unstable woman so that he seems unavailable. Randall offers a job to a high school classmate, now a hobo, to make amends for ruining the man's life.
The Arrival
episode S6.E1 september 2001Mike Flaherty unexpectedly visits from Washington, meets his replacement Charlie, and ruins Charlie's attempts at wooing Caitlin. Meanwhile, Randall begins dating Judge Claire Simmons, who is separated from her husband, but not divorced.
A Tree Falls in Manhattan
episode S6.E2 september 2001Randall tries to impress Claire by having a tree cut down, only to find out that the tree is an historic landmark. And Charlie tells it to a stranger, who turns out to be the campaign manager for Randall's opponent Julian Wheeler.
Wife with Mikey
episode S6.E3 october 2001Mike's engagement falls through, so he immerses himself in his old job at City Hall, aggravating Charlie. Randall prepares for a charity fund raiser.
The Apartment
episode S6.E4 october 2001When Randall's approval rating drops because of his relationship with Claire, Charlie advises him to be discreet; so Randall and Claire freeload on Charlie. Paul hires a publicist.
Yet Another Stakeout
episode S6.E5 october 2001Charlie and Caitlin obtain damaging photos of Julian Wheeler in retaliation for him slamming Randall in campaign ads. Carter's coworkers help impress an adoption agency official and friend Michelle strikes up a friendship with Stuart.
Yeah Baby!
episode S6.E6 october 2001Randall's campaign consultant Robin has psychic gifts, which predict impending disaster for Charlie. Stuart dates the surrogate mother of Carter's child and realizes that he himself may be the father.
Sleeping with the Enemy
episode S6.E7 november 2001Charlie sleeps with Julian Wheeler's campaign manager Jennifer Duncan. Caitlin and Paul both befriend Robin Jones, but Randall thinks Robin is only using Paul for sex. Randall's approval rating is up with young voters.
She's Gotta Habit
episode S6.E8 november 2001Charlie and Caitlin have lunch with Jennifer, who makes a startling confession. A cooling between Randall and Judge Claire Simmons puts Paul's divorce settlement from Claudia in jeopardy.
The Wedding Scammer
episode S6.E9 november 2001Caitlin's mother (played by Michelle Phillips) has been pressuring Caitlin to get married so she passes off Charlie as her boyfriend at her cousin's wedding. Paul is invited to a fashion show by a childhood friend (played by Rhea Durham).
Fight Flub
episode S6.E10 november 2001The mayor's opposing candidate makes fitness a campaign issue but the opposition's wife (played by Elizabeth Mitchell) runs in his place after he has a heart attack. Charlie and Caitlin help each other out of bad dates.
Chinatown
episode S6.E11 november 2001On Election Day, the staff is nervous over the close race. Mayor Winston proposes to Claire (played by Farrah Fawcett) while Charlie continues his relationship with Jennifer (played by Denise Richards).
An Office and a Gentleman
episode S6.E12 december 2001Randall delegates Charlie to decide which staff member will move into a beautiful new office. Caitlin tries to find out what the City Hall Santa Claus looks like before she dates him.
O Mother, Where Art Thou?
episode S6.E13 january 2002Randall's new girlfriend Christine is the receiver of his late mother's artificial heart. Caitlin dates an older man named Tom while Charlie dates Tom's daughter, and the four of them wind up in family counseling.
Rags to Riches
episode S6.E14 march 2002Carter's dog dies. The mayor looks into charitable foundations to make a donation. Meanwhile, Caitlin surprises Charlie on his birthday with a visit by his estranged con man father (played by Martin Sheen).
Sex, Lies and Video Date
episode S6.E15 march 2002Randall asks Charlie to keep tabs on his niece Stephanie, who makes passes at him. Paul's latest gaff is of the romantic variety and takes place on a "Blind Date" TV show. Carter buys an expensive coat and Randall purchases a new Corvette.
Eyes Wide Open
episode S6.E16 march 2002Randall's insomnia is linked to Paul receiving a lucrative job offer from a senator. Carter joins the Big Brother program, but his visiting Little Brother Spencer winds up spending time with Caitlin and a very uncomfortable Charlie.
Age Against the Machine
episode S6.E17 march 2002Charlie is exhausted from keeping up with his much-younger girlfriend Tracy. Gay art dealer Martin Davis invites Randall, Carter, and Stuart to a fund raiser, where Martin and Carter might hit it off.
An Affair Not to Remember
episode S6.E18 april 2002Paul feels depressed when his divorce is finalized, so Carter feigns heterosexuality to help him play the dating game. Charlie and Caitlin have a flashback to their first meeting - in 1988 during a political event for Michael Dukakis.
Let's Give Them Something to Talk About
episode S6.E19 april 2002A therapist helps Caitlin sort out her feelings for both Tom Crandall and Charlie. Carter tries to help Paul to prepare for an appearance on Larry Elder's call-in radio program.
Look Who's Not Talking
episode S6.E20 april 2002Stuart extends his vacation, so a temporary replacement is hired and performs better than Stuart does. After much thought, Caitlin breaks off her relationship with Tom Crandall.
A Tale of Four Cities
episode S6.E21 april 2002At a mayors' conference, Caitlin feels awkward because Charlie once had an affair with the organizer, so Caitlin tries to make Charlie jealous. Randall renews his long-standing professional rivalry with Mayor Stone Taylor of Los Angeles.
A Friend in Need
episode S6.E22 april 2002Randall tries to please visiting Governor Riley. Charlie and Caitlin struggle to keep their affair secret and Stuart senses there's something strange in the office. Carter is getting a foster child.
- Pilot
- The Great Pretender
- The Apartment
- Pride and Prejudice
- The Rivals
- A Star Is Born
- Grand Illusion
- The High and the Mighty
- Meet Tommy Dugan
- The Competition
- Dog Day Afternoon
- Criss Cross
- Bye Bye Love
- Starting Over
- Gabby's Song
- Kiss Me, Stupid
- An Affair to Remember
- Snowbound
- Striptease
- Deaf Becomes Her
- Hot in the City
- Bone Free
- The Mayor Who Came to Dinner
- Mayor Over Miami
- Paul Flew Over the Cuckoo's Nest
- Porn in the U.S.A.
- Wonder Woman
- The Goodbye Girl
- In the Heat of the Day
- Radio Daze
- The Thirty Year Itch
- My Life Is a Soap Opera
- Family Affair
- Family Affair: Part 2
- They Shoot Horses, Don't They?
- Miracle Near 34th Street
- Same Time Next Year
- The Paul Lassiter Story
- Gentleman's Agreement
- Deaf Man Walking
- The Marrying Men
- One Wedding and a Funeral
- A River Runs Through Me
- The Pope of Gracie Mansion
- Bye, Bye, Birdie
- The Lady or the Tiger
- Single White Male
- The Paul Bearer
- Dead Dog Talking
- There's Something About Heidi
- Gone with the Wind
- The Deer Hunter
- It Happened One Night
- Three Men and a Little Lady
- An Officer and a Gentleman
- Quest for Fire
- The Kidney's All Right
- Gobble the Wonder Turkey Saves the Day
- Local Hero
- Monkey Business
- Taxi Driver
- The Nutty Deputy Mayor
- Not in the Line of Fire
- Internal Affairs
- Dick Clark's Rockin' Make-Out Party '99
- Back to the Future IV - Judgment Day
- Politically Incorrect
- That's Entertainment
- The Last Temptation of Mike
- Carter & Stuart & Bennett & Deirdre
- The Mayor with Two Brains
- Wall Street
- Klumageddon: Part 1
- Klumageddon: Part 2
- Catcher in the Bronx
- James and the Giant Speech
- All the Mayor's Men
- These Shoes Were Made for Cheatin'
- Rebel Without a Chair
- The Mayor May Not
- The Great Debate
- How to Bury a Millionaire
- The Thanksgiving Show
- The Doorman Always Rings Twice
- Mustang Mikey
- My Dinner with Caitlin
- A Tale of Two Sisters
- Casino
- The Marry Caitlin Moore Show
- Suffragette City
- Mike's Best Friend's Boyfriend
- The Pig Whisperer
- Uneasy Rider
- About Last Night
- Don't Get on the Bus
- Airplane!
- An American Deputy Mayor in Paris
- The Commitments
- Goodbye: Part 1
- Goodbye: Part 2
- Hello Charlie
- Smile
- The Spanish Prisoner
- The Bone Collectors
- Blind Faith
- Balloons over Broadway
- Lost and Found
- All the Wrong Moves
- The Burgers of Wrath
- Toy Story
- The Perfect Dorm
- Hey Judith
- The Gambler
- In the Company of Dudes
- The Image Maker
- Trainstopping
- Rain on My Charades
- You've Got Male
- Minor League
- Science Friction
- Brotherly Love
- A Shot in the Dark: Part 1
- A Shot in the Dark: Part 2
- The Arrival
- A Tree Falls in Manhattan
- Wife with Mikey
- The Apartment
- Yet Another Stakeout
- Yeah Baby!
- Sleeping with the Enemy
- She's Gotta Habit
- The Wedding Scammer
- Fight Flub
- Chinatown
- An Office and a Gentleman
- O Mother, Where Art Thou?
- Rags to Riches
- Sex, Lies and Video Date
- Eyes Wide Open
- Age Against the Machine
- An Affair Not to Remember
- Let's Give Them Something to Talk About
- Look Who's Not Talking
- A Tale of Four Cities
- A Friend in Need
Best moments10
- Mike courts a wealthy NYC socialite to fund Randall's Senate campaign, which Caitlin bankrupted. Nikki and Janelle compete to mentor a hunky intern. Paul moves in with coworkers temporarily after a tiff with Claudia.
- Confiscated toys may become part of a photo op for Randall, who undermines Charlie's staff meetings. Carter persuades Caitlin to volunteer with him in a retirement home. Paul seeks jokes to enliven the City Hall holiday greeting card.
- Mike and Randall clash repeatedly with an obnoxious deejay. Paul tries to write an objective critique of Randall's autobiography. The female staffers fantasize about the handsome man who delivers bottled water to the building.
- Caitlin's mother (played by Michelle Phillips) has been pressuring Caitlin to get married so she passes off Charlie as her boyfriend at her cousin's wedding. Paul is invited to a fashion show by a childhood friend (played by Rhea Durham).
- When Randall's approval rating drops because of his relationship with Claire, Charlie advises him to be discreet; so Randall and Claire freeload on Charlie. Paul hires a publicist.
- On Election Day, the staff is nervous over the close race. Mayor Winston proposes to Claire (played by Farrah Fawcett) while Charlie continues his relationship with Jennifer (played by Denise Richards).
- Randall is depressed after signing divorce papers. Claudia pursues Paul. So both men skip town for Miami, leaving the other staffers to cover for them. Stuart has a personality change due to his new girlfriend.
- An abrasive blind man finds Caitlin dull, spurns her, and causes her to try to improve her personality. In need of a religion refresher, Randall and Charlie accidentally wreak havoc on Claudia's religious education class and her future.
- At a mayors' conference, Caitlin feels awkward because Charlie once had an affair with the organizer, so Caitlin tries to make Charlie jealous. Randall renews his long-standing professional rivalry with Mayor Stone Taylor of Los Angeles.
- The mayor's opposing candidate makes fitness a campaign issue but the opposition's wife (played by Elizabeth Mitchell) runs in his place after he has a heart attack. Charlie and Caitlin help each other out of bad dates.
- The Great Debate
- Toy Story
- Radio Daze
- The Wedding Scammer
- The Apartment
- Chinatown
- Mayor Over Miami
- Blind Faith
- A Tale of Four Cities
- Fight Flub