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Main Characters
Mike Flaherty
Mike Flaherty (Michael J. Fox)
The Deputy Mayor- The Casanova: A season three episode features all the women Mike dated on the show so far, which was no small amount, and included Heidi Klum.
- Hypercompetent Sidekick: He's much more efficient than the inept Mayor.
- Only Sane Man: The most reasonable and competent person in his workplace. Though he has flaws on his own, they are not very noticeable compared to his co-workers.
- Put on a Bus: After season 4, he takes a metaphorical bullet for the Mayor by taking the heat for some alleged mob connections, then resigns from his post.
- Really Gets Around: As demonstrated by a third season episode, Mike has had a lot of girlfriends.
- Will They or Won't They?: He has an on/off relationship with Nikki in season 3, but it's ultimately dropped in favour of his Ship Tease with Caitlin in season 4.
Ashley Schaeffer
Ashley Schaeffer (Carla Gugino)
City Hall Reporter- The Bus Came Back: She returns for one episode in season three.
- Put on a Bus: After only 12 episodes. She was initially the Deuteragonist besides being Mike's girlfriend. Once it was discovered that Mike was better off chasing girls romantically, she was written off the show, with her leaving Mike for some dream job. He mopes for an episode, and she's rarely dealt with again.
Mayor Winston
Mayor Randall Winston (Barry Bostwick)
- And Starring: "and Barry Bostwick as the Mayor".
- Bunny-Ears Lawyer: At least in the early seasons. He often depended on Mike, but he was a lot more savvy than expected. "Grand Illusion" and "Radio Daze" offer good examples of this. In the former episode, he knows exactly how to save face politically with Carter's marriage protest (whereas Mike panics). In the latter, the Mayor matches wits with a shock jock and makes a fool out of him on his own show.
- Cloudcuckoolander: While he comes through in the occasional crisis and was much more normal in Season 1, he's clearly not very bright or rational much of the time.
- Crouching Moron, Hidden Badass: The Mayor is shrewder than one would think, especially in a tight race.
- Flanderization: The Mayor began as a competent and intelligent elected official who depended on Mike's organizational skills; in later episodes, it seems improbable that he would have been elected to anything in the first place.
- Pointy-Haired Boss: He's a clueless Mayor, so his Hypercompetent Sidekick Mike is the one truly in charge.
Paul Lassiter
Paul Lassiter (Richard Kind)
Press Secretary- Butt-Monkey:
- He once got sued for getting shot in the head because it cost a security guard his job. Successfully!
- At one point when talking about how to handle a scandal, nearly everyone suggests firing Paul, even people who never met him personally. And even Paul himself!
- Cutting Corners: Paul will go to any length to avoid paying money for anything.
- The Friend Nobody Likes: His co-workers occasionally tolerate him, but more out of pity than anything else.
- Happily Married: Is married to Claudia for a good part of the show, but she leaves him in season 5.
- Manchild: Because of his neurotic and childish nature, he often screws up.
- Straw Loser: A pathetic character who pretty much exists to make Mike and everyone else look better.
- Vetinari Job Security: Carter calls out Paul on having a job that he feels is far too easy and anybody could do. Paul accepts this challenge and tries to prepare him for a press conference, teaching him the vital skill of shutting down conversation by repeating HUH? over and over. Once confronted with real journalists, Carter quickly realizes Paul has a job much more difficult than it seems on the surface.
Stuart Bondek
Stuart Bondek (Alan Ruck)
Assistant Deputy Mayor- Blind Without 'Em: Stuart, as revealed in the NYPD Blue spoof scene in "They Shoot Horses, Don't They?".Stuart: (removing each item in succession) Take my keys, take my belt, take my glasses. (immediately crashes into the table) Give me my glasses.
- Formerly Fat: In "The Image Maker," it's revealed he used to be married to a highly-critical woman who caused him so much emotional grief, he gained 100 pounds from stress eating.
- Kavorka Man: He's played by the gawky, nerdy-looking Alan Ruck, and had some hot girlfriends, from the evil psychotic Dierdre, to a childhood friend played by Lori Laughlin.
- Lovable Sex Maniac: He's a sex-obsessed character but his antics are Played for Laughs.
- Really Gets Around: Due to being a Kavorka Man, he has been said to have a date every week, though how far the dates go is never clear. Carter does say at one point that Stuart hasn't slept alone since his bed was a tiny racecar.
Carter Heywood
Carter Heywood (Michael Boatman)
Director of Minority Affairs- Gay Best Friend: To Mike (who actually calls him his best friend) and Stuart in particular. But he's also a good sounding board for most of the cast, particularly Nikki who frequently asks him for relationship advice.
- Have I Mentioned I Am Gay?: At least Once an Episode, either he or another character (usually Stuart) will mention his orientation.
- Only Sane Man: Like Mike, he's another character who often serves as the voice of reason.
- Twofer Token Minority: Black and gay, he's hired to clean up the mess when Mayor Winston makes a gaffe in talking about a gay rights march.
Nikki Faber
Nikki Faber (Connie Britton)
City Hall Accountant- Chuck Cunningham Syndrome: She leaves the show after season 4, without any explanation.
- Ethical Slut: How Nikki was portrayed in the beginning, dating many men but never portrayed as a bad person.
- Fiery Redhead: Her outgoing and confident personality matches her red hair.
- Sexy Secretary: An accountant who is considered attractive, sometimes to Ms. Fanservice levels.
- Will They or Won't They?: She has an on/off relationship with Mike in season 3, but it's ultimately dropped in favour of Mike/Caitlin in season 4.
James Hobert
James Hobert (Alexander Chaplin)
Mayoral Speech Writer- Chuck Cunningham Syndrome: He leaves the show after season 4, without any explanation.
- Flanderization: In earlier seasons, James was just a run-of-the-mill nice guy from a small town, and not the unbelievably naive rube he became later on.
Janelle Cooper
Janelle Cooper (Victoria Dillard)
Executive Assistant to the Mayor- Character Catchphrase: "Damn!"
- Chuck Cunningham Syndrome: She leaves the show after season 4, without any explanation.
- Sleeping with the Boss: Briefly dates the Mayor in season 3.
Stacey Paterno
Stacey Paterno (Jennifer Esposito)
- Chuck Cunningham Syndrome: She leaves after season 3, for unknown reasons.
- Really Gets Around: A rough-around-the-edges Italian secretary who is implied to be promiscuous.
- Sexy Secretary: Mike's secretary in season 2 and 3, and is portrayed as a hot Ms. Fanservice character.
Caitlin Moore
Caitlin Moore (Heather Locklear)
Initially the Mayor's Senate Campaign Manager, later the City Hall Communication Director- Everyone Loves Blondes: She's blonde, and both lead characters of the show are attracted to her. In one of the later episodes, she worries that her only attractive trait is her physical appearance.
- Will They or Won't They?: She has an on/off relationship with Mike in season 4. After Mike is Put on a Bus, she develops a similar relationship with Mike's replacement Charlie.
Charlie Crawford
Charlie Crawford (Charlie Sheen)
Deputy Mayor after Mike leaves the show- Really Gets Around: He's a more attractive and successful version of Stuart.
- Suspiciously Similar Substitute: To Mike, after he replaces him as the show's lead character. He has Mike's job, is known for being The Casanova (possibly more than Mike), and has a Ship Tease with Caitlin.
Angie Ordonez
Angie Ordonez (Lana Parrilla)
Charlie's secretary in season 5- Flat Character: Despite being added to the cast in the opening titles, her screentime in each episode is extremely small, with no more than a few lines of dialogue an episode. Thus, her character is never really developed in any way.
