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| Episode 1 - [Catcher In The Bronx] |
| Details : When Mike says: Let's not get so dramatic okay? This is not some cheesy soap opera. he refers to Heather Locklear's long-time role as Amanda Woodward in the soap Melrose Place. |
| Guest Cast and Crew : Chris Berman | Heidi Klum | Roger Clemens | James Carville | |
| Air Date : Sep. 21, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 2 - [James And The Giant Speech] |
| Details : James struggles to write an important speech to keep himself from being fired by Caitlin. Meanwhile Paul is worried that Caitlin wants his office; she ends up moving into Mike's. And Nikki breaks up with Mike. |
| Guest Cast and Crew : Nipsey Russell | |
| Air Date : Sep. 28, 1999 | Rating ➦ ★★★★★★★ |
| Episode 3 - [All The Mayor's Men] |
| Details : Caitlin implants secret background checks on all City Hall employees. Mike Stuart and Carter break into her office to see the files. Caitlin goes to Nikki and Janelle's girls' night out. The mayor is offered a part in a movie filming in New York. |
| Guest Cast and Crew : Matt Besser | |
| Air Date : Oct. 05, 1999 | Rating ➦ ★★★★★★★ |
| Episode 4 - [These Shoes Were Made For Cheatin'] |
| Details : Mike tricks Nikki into seeing a couples counselor. The mayor takes an eighth grade test after being challenged by junior-high students. Stuart attempts to join Carter's gay gym to meet women. |
| Guest Cast and Crew : Writer : Tad Quill | |
| Air Date : Oct. 12, 1999 | Rating ➦ ★★★★★★★ |
| Episode 5 - [Rebel Without A Chair] |
| Details : Carter is named Activist of the Year. Stuart has a new paperweight that looks like a breast. Mike's continued jealousy of Caitlin causes him to make remarks to a gay magazine which is misinterpreted outing himself and the mayor. Paul is banned from the bathroom after insulting the new attendant. |
| Guest Cast and Crew : Boomer Esiason | |
| Air Date : Oct. 19, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 6 - [The Mayor May Not] |
| Details : The mayor considers quitting the senatorial race teaming Mike and Caitlin to stop him. Carter becomes a kept man and Paul and James scheme to play a good practical joke on Stuart. |
| Guest Cast and Crew : Julius Carry | Al D'Amato | |
| Air Date : Nov. 02, 1999 | Rating ➦ ★★★★★★★ |
| Episode 7 - [The Great Debate] |
| Details : Claudia's mother kicks Paul out of his house so he moves in with Stuart and Carter. Nikki dates the office's new young male intern. And Mike courts a wealthy socialite to donate money when the mayor's campaign runs out. |
| Guest Cast and Crew : Amy Irving | Michael Hobert | |
| Air Date : Nov. 09, 1999 | Rating ➦ ★★★★★★★ |
| Episode 8 - [How To Bury A Millionaire] |
| Details : Mike and Caitlin agree to share the mayor on odd even days. On Caitlin's day Mike borrows the mayor to visit a kid who fell in a well. Unfortunately they're 20 minutes late and the mayor falls in the now vacant well. Carter puts Rags in doggie day care. Paul appears on Who Wants to Be a Millionaire and wins $1000000. Stuart negotiates with firemen. |
| Guest Cast and Crew : Deirdre Lovejoy | Regis Philbin | Marceline Hugot | |
| Air Date : Nov. 16, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 9 - [The Thanksgiving Show] |
| Details : A newly rich Paul thinks Caitlin is hitting on him. The mayor wants a senator's endorsement and invites him along with his staff to Gracie Mansion for Thanksgiving. The senator thinks that Mike and Caitlin are a couple so they must share a room. Stuart and Deidre are back together. |
| Guest Cast and Crew : John McMartin | Beth Littleford | Writer : Richard Day | |
| Air Date : Nov. 23, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 10 - [The Doorman Always Rings Twice] |
| Details : Paul has invested in a politically themed restaurant. Mike struggles to run the city while the mayor is out of town. Deidre is stalking Caitlin a la Single White Female. |
| Guest Cast and Crew : Frank Santorelli | Beth Littleford | Writer : Tim Hobert | |
| Air Date : Nov. 30, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 11 - [Mustang Mikey] |
| Details : Mike celebrates his five-year anniversary working for the mayor by taking Caitlin and going on a joyride with the mayor's '66 Mustang. Nikki and Carter accuse each other of being vain when City Hall ID photos are taken. The mayor wants to rekindle his romance with Janelle. Caitlin's busy schedule forces James back to speechwriting; he hires Deidre to be Mike's new secretary. |
| Guest Cast and Crew : Beth Littleford | |
| Air Date : Dec. 07, 1999 | Rating ➦ ★★★★★★★ |
| Episode 12 - [My Dinner With Caitlin (Ak a Christmas 1999)] |
| Details : Mike invites Caitlin to his Christmas party as his only guest but his plans at romance are spoiled when she arrives with a date. Paul finds John McEnroe's headband in the City Hall clothing drive box. James finds a second job as a suicide hotline operator. Stuart installs a chin-up bar in the mayor's office which the mayor promptly injures himself on. |
| Guest Cast and Crew : Gordon Joseph Weiss | Writer : Bill Callahan | |
| Air Date : Dec. 21, 1999 | Rating ➦ ★★★★★★★ |
| Episode 13 - [A Tale Of Two Sisters] |
| Details : The mayor struggles to find a date for a mayor's conference. Mike goes out with Caitlin's sister making Caitlin jealous. Stuart tries to join Nikki James and Janelle's art class to see nude women. Paul is upset that Carter makes more money than him. |
| Guest Cast and Crew : Christine Taylor | |
| Air Date : Jan. 12, 2000 | Rating ➦ ★★★★★★★★ |
| Episode 14 - [Casino] |
| Details : Paul's cheap dentist puts braces on James instead of removing his infected tooth causing problems in James' date with the new mail girl. The city's raffle to raise money for the Big Buddy program is screwed up when Paul skimps on the raffle tickets. Stuart and Carter blackmail Caitlin to decrease their workload. |
| Guest Cast and Crew : Writer : Tim Hobert | |
| Air Date : Feb. 02, 2000 | Rating ➦ ★★★★★★★★ |
| Episode 15 - [The Marry Caitlin Moore Show] |
| Details : After eating some of Rags' dog food Paul develops a rash before he appears on The View. Nikki helps him discover the wonders of makeup though. Stuart tries to convince James that he's gay. Mike hires a hotshot director to film the mayor's Senate commercial unaware that Trevor is Caitlin's ex-husband. After the commercial turns out to be a flop and Mike fires Trevor Caitlin accuses him of being jealous. When a talk with Nikki persuades Mike to express his feelings for Caitlin he sees her and Trevor in a heated embrace. |
| Guest Cast and Crew : Star Jones | Lisa Ling | Meredith Vieira | Writer : Tad Quill | Director : John Fortenberry | |
| Air Date : Feb. 09, 2000 | Rating ➦ ★★★★★★★★ |
| Episode 16 - [Suffragette City] |
| Details : To quell a protest by senior citizens Mike plans to get the city's first woman voter to vote for the mayor. When Mike finds out that Trevor isn't really British he must decide whether to tell Caitlin or not. Carter protests anti-gay discrimination in an apartment building. James and Paul fight over a hey guy. |
| Guest Cast and Crew : Alice Drummond | John C. Vennema | Brad Raider | |
| Air Date : Feb. 16, 2000 | Rating ➦ ★★★★★★★★ |
| Episode 17 - [Mike's Best Friend's Boyfriend] |
| Details : While a reporter visits City Hall to do a story on Paul the mayor thinks she's really there for him. Mike thinks Carter's boyfriend is hitting on him. The staff looks for good samaritans for a dinner. Stuart tries to convince James that he's getting fat. |
| Guest Cast and Crew : James Patrick Stuart | Writer : Dawn Urbont | |
| Air Date : Feb. 23, 2000 | Rating ➦ ★★★★★★★ |
| Episode 18 - [The Pig Whisperer] |
| Details : Mike has a meeting with a tomato stand owner who refuses to move his stand so that the city can build a new performing arts center. He ultimately enlists James to compete against the man in a pig-off to decide whether the stand will stay or move. The mayor befriends a rapper who sampled one of his speeches in a song. Paul and Deirdre have memories of having sex at a concert 20 years before driving Stuart jealous. |
| Guest Cast and Crew : Kevin Mambo | Beth Littleford | |
| Air Date : Mar. 08, 2000 | Rating ➦ ★★★★★★★ |
| Episode 19 - [Uneasy Rider] |
| Details : Mike helps the mayor deal with his feelings when his father unexpectedly dies. James thinks Caitlin has a crush on him. Paul's magic eight ball proves helpful to the staff. |
| Guest Cast and Crew : Cody Arens | Writer : Tim Hobert | |
| Air Date : Mar. 22, 2000 | Rating ➦ ★★★★★★★ |
| Episode 20 - [About Last Night] |
| Details : With the President coming to visit City Hall Mike is upset when Caitlin gets to meet him instead until plans change. The rest of the staff gathers at the bar where Caitlin joins them. Nikki and Carter bet on who can pick up more women. Stuart tries to get Caitlin drunk; he succeeds and she leaves a drunken message for Mike. Paul tries to get James to help take his picture with the President. |
| Guest Cast and Crew : Judah Friedlander | Writer : Tad Quill | |
| Air Date : Apr. 19, 2000 | Rating ➦ ★★★★★★★★ |
| Episode 21 - [Don't Get On The Bus] |
| Details : The mayor prepares for a three-day trip across New York on his new campaign bus. Paul and James grow mustaches when they think that Carter's gets him the best assignments. Nikki becomes a female version of Stuart when she consults him for dating advice. After Mike discovers that Trevor has asked Caitlin to marry him again he accidentally hits him with the bus. Mike and Caitlin kiss but their session is interrupted when Mike reveals he was deliberately aiming for Trevor. |
| Guest Cast and Crew : Bill Patrick | Writer : Bill Callahan | |
| Air Date : Apr. 26, 2000 | Rating ➦ ★★★★★★★★ |
| Episode 22 - [Airplane!] |
| Details : While Michael and Caitlin fly to San Francisco Stuart joins Carter for a protest and the mayor tries to have a light bulb changed. |
| Guest Cast and Crew : Deirdre Lovejoy | Rachel Jacobs | Patrick Ewing | |
| Air Date : May. 03, 2000 | Rating ➦ ★★★★★★★ |
| Episode 23 - [An American Deputy Mayor In Paris] |
| Details : Caitlin prepares to marry Trevor and elopes to Paris where Mike follows and reveals that he loves her. James becomes angered with the mayor when he receives an undeserved war award. Stuart asks Nikki to pose for a charity swimsuit calendar. |
| Guest Cast and Crew : Writer : Bill Callahan | |
| Air Date : May. 10, 2000 | Rating ➦ ★★★★★★★★ |
| Episode 24 - [The Commitments] |
| Details : Mike and Caitlin return from Paris as a couple. Caitlin wants more than a physical relationship so Mike bets her that he can resist her for a week while tries to break his willpower. The mayor falls in love with Rags after filming an animal rights commercial with him. |
| Air Date : May. 17, 2000 | Rating ➦ ★★★★★★★★★ |
| Episode 25 - [Goodbye Part 1] |
| Details : Mike discusses his attempts to have sex with Caitlin with his new therapist. Nikki's new boyfriend is too likable. Caitlin isn't in the mood when Mike is. A reporter accuses the mayor of being involved in organized crime; Nikki's boyfriend turns out to be a mobster who has been getting the office staff to do favors for him. Mike weighs giving his friends up but ultimately throws himself on his sword and takes all blame. |
| Guest Cast and Crew : Michael Gross | John Bedford Lloyd | |
| Air Date : May. 24, 2000 | Rating ➦ ★★★★★★★★ |
| Episode 26 - [Goodbye Part 2] |
| Details : Mike and Caitlin have sex. The staff works damage control but Mike ultimately fires himself to save everybody else. The staff says their goodbyes at the bar. Caitlin promises Mike that she's not going anywhere. Mike says goodbye to the mayor and walks out of City Hall for the last time. Six weeks later Mike turns up as an environmental lobbyist in DC. |
| Guest Cast and Crew : John Bedford Lloyd | Writer : Bill Lawrence | |
| Air Date : May. 24, 2000 | Rating ➦ ★★★★★★★★★★ |