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| Episode 1 - [Hello Charlie] |
| Details : Charlie Crawford is late for his first press conference as the new deputy mayor. He later runs into trouble trying to settle a tollbooth workers strike when their lawyer is an ex-flame of his. |
| Guest Cast and Crew : Kimberley Davies | Marcia Cross | Director : Ted Wass | |
| Air Date : Oct. 18, 2000 | Rating ➦ ★★★★★★★ |
| Episode 2 - [Smile] |
| Details : Charlie tries to get the mayor to a dentist before an important photo shoot. Caitlin hires a new male assistant only because he's attractive. Carter and Stuart deal with someone who keeps parking a bike in their parking space. |
| Guest Cast and Crew : Geoff Stults | Dabbs Greer | Eric Stonestreet | Chrissie Carnell | Writer : Chris Henchy | Director : Ted Wass | |
| Air Date : Oct. 25, 2000 | Rating ➦ ★★★★★★★ |
| Episode 3 - [The Spanish Prisoner] |
| Details : Caitlin causes a misunderstanding when she believes that Charlie is taking a Spanish class to improve relations with the Latin American community. Paul and the mayor struggle to create office water-cooler talk. Stuart becomes jealous of the time Carter has been spending with Caitlin. |
| Guest Cast and Crew : Joel McKinnon Miller | Kevin Ruf | Kal Penn | Director : Ted Wass | Writer : Bill Callahan | |
| Air Date : Nov. 01, 2000 | Rating ➦ ★★★★★★★ |
| Episode 4 - [The Bone Collectors] |
| Details : Caitlin auditions for the job of co-host on Live with Regis. Stuart and Paul work together supervising after bones are discovered under the Westside Highway. The mayor has an audio visual link connected to the office while he is on vacation. |
| Guest Cast and Crew : Sam Lloyd | Stuart Fratkin | Regis Philbin | Director : Ted Wass | Writer : Tim Hobert | |
| Air Date : Nov. 08, 2000 | Rating ➦ ★★★★★★★ |
| Episode 5 - [Blind Faith] |
| Details : Caitlin goes out of her way to prove that she's fun after a blind man won't date her because she's not. Charlie accidentally talks Claudia into becoming a nun; she leaves Paul. The mayor researches religion. |
| Guest Cast and Crew : Francis Guinan | Sarah Shahi as Bachelorette | Landry Allbright | Dave Allen | Director : Ted Wass | |
| Air Date : Nov. 15, 2000 | Rating ➦ ★★★★★★★ |
| Episode 6 - [Balloons Over Broadway] |
| Details : 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. |
| Guest Cast and Crew : Alex Rice | Raquel Welch | Director : Ted Wass | |
| Air Date : Nov. 22, 2000 | Rating ➦ ★★★★★★★ |
| Episode 7 - [Lost And Found] |
| Details : Caitlin and Charlie fight the attention of Caitlin's new friend. Carter Stuart and Paul compete for a trip to New Orleans with the mayor. |
| Guest Cast and Crew : Samm Levine | Director : Ted Wass | Writer : Hadley Davis | Writer : Bonnie Schneider | |
| Air Date : Nov. 29, 2000 | Rating ➦ ★ |
| Episode 8 - [All The Wrong Moves] |
| Details : 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. |
| Guest Cast and Crew : Eddie McClintock | Rusty Joiner | Director : Ted Wass | |
| Air Date : Dec. 06, 2000 | Rating ➦ ★★★★★★★ |
| Episode 9 - [The Burgers Of Wrath] |
| Details : Mike has been in Zimbabwe for three weeks so Paul teaches Caitlin about celibacy. Stuart convinces Angie that he's a biker guy. War on unemployment forces the mayor to work at a burger joint. |
| Guest Cast and Crew : Michael Hobert | Director : Ted Wass | |
| Air Date : Dec. 13, 2000 | Rating ➦ ★★★★★★★ |
| Episode 10 - [Toy Story] |
| Details : 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. |
| Guest Cast and Crew : Dakota Fanning | Writer : Chris Henchy | Director : Ted Wass | |
| Air Date : Dec. 20, 2000 | Rating ➦ ★★★★★★★ |
| Episode 11 - [The Perfect Dorm] |
| Details : In an attempt to get over Claudia Paul decides to move into a college dorm. Caitlin tries dating after ending her relationship with Mike--but doesn't have much luck. The Mayor builds an access ramp after he gets caught parking in a handicapped parking space. |
| Guest Cast and Crew : Robert Maschio | Director : Ted Wass | Writer : Tim Hobert | |
| Air Date : Jan. 10, 2001 | Rating ➦ ★★★★★★★ |
| Episode 12 - [Hey Judith] |
| Details : Caitlin sets the mayor up with her neighbor Judith who becomes way too much of an influence on the mayor. Carter helps Stuart prepare for a million dollar shot at a Rangers' game. Paul thinks he's Canadian. |
| Guest Cast and Crew : Barry Melrose | Director : Ted Wass | |
| Air Date : Jan. 17, 2001 | Rating ➦ ★★★★★★★ |
| Episode 13 - [The Gambler] |
| Details : Paul Stuart and Carter rope reformed gambler Charlie into their poker night and are responsible for his subsequent gambling bender. Caitlin tries to teach the mayor to be more self-sufficient. |
| Guest Cast and Crew : John David Conti | Director : Ted Wass | Writer : Bill Callahan | |
| Air Date : Jan. 24, 2001 | Rating ➦ ★★★★★★★ |
| Episode 14 - [In The Company Of Dudes] |
| Details : When a supermodel sues the mayor Charlie hires his old college friend to defend him. Charlie finds himself torn between two friends after Scott hits on Caitlin. Meanwhile Paul and Stuart compete for the same woman. |
| Guest Cast and Crew : Sally Wheeler | Jason Priestley | Director : Ted Wass | |
| Air Date : Feb. 07, 2001 | Rating ➦ ★★★★★★★ |
| Episode 15 - [The Image Maker] |
| Details : Carter discovers an old love letter written by Stuart. He decides to set Stuart up with the addressee of the letter a woman who turns out to be Stuart's ex-wife. The woman quickly manages to set a whipped Stuart into his old rut. Meanwhile Caitlin hires an image consultant when the mayor's approval ratings go down. The consultant discovers that the mayor has a problem with women causing Charlie to make himself over. And also Paul worries that he's unrecognizable. |
| Guest Cast and Crew : Kaitlin Hopkins | Joanna Going | Director : Ted Wass | Writer : Bill Callahan | |
| Air Date : Feb. 14, 2001 | Rating ➦ ★★★★★★★ |
| Episode 16 - [Trainstopping] |
| Details : Julia's having a hard time dealing with her kiss with Charlie so he asks her out. Their first date is a nightmare. Meanwhile the mayor and his staff take the subway to prove that the mayor is in touch with the people. The train gets stuck in a tunnel screwing up Charlie's plans for a second date. Meanwhile Paul tells an exclusive cafe that Carter is Cuba Gooding Jr. to get reservations. |
| Guest Cast and Crew : Beth Riesgraf | Director : Ted Wass | Writer : Tim Hobert | |
| Air Date : Feb. 21, 2001 | Rating ➦ ★★★★★★★ |
| Episode 17 - [Rain On My Charades] |
| Details : The mayor's daughter Meg returns and inspires Caitlin to be more spontaneous and free. Paul Stuart and Carter give Charlie advice about compromising with Julia. This leads to Charlie deciding he's ready to commit while Julia decides she's not. |
| Guest Cast and Crew : Alyssa Milano | Branden Williams | Joanna Going | Seth Meyers | Director : Ted Wass | |
| Air Date : Feb. 28, 2001 | Rating ➦ ★★★★★★★ |
| Episode 18 - [You've Got Male] |
| Details : Stuart is hired to write a porno movie. Charlie and Caitlin compete for a donation from a wealthy male chauvinist. After Paul poses as the Mayor's son for a golf tournament he becomes confused when the Mayor actually begins paying attention to him. |
| Guest Cast and Crew : Alex Kapp | Sam McMurray | Director : Ted Wass | |
| Air Date : Apr. 25, 2001 | Rating ➦ ★★★★★★★★ |
| Episode 19 - [Minor League] |
| Details : Charlie tries out for a minor league baseball team trying to relive his high school glory days. Caitlin encourages the pitcher to go easy on him. The mayor receives a death threat so he gets a bodyguard. After discovering that his job requires him to come into contact with the mayor so often Paul receives a bodyguard also. Rags spends a day at the office. |
| Guest Cast and Crew : Blake Clark | Josh Braaten | Bob Costas | Director : Ted Wass | Writer : Bill Callahan | |
| Air Date : May. 02, 2001 | Rating ➦ ★★★★★★★★ |
| Episode 20 - [Science Friction] |
| Details : Caitlin falls hard for a rich young sexy philanthropist. The Mayor is threatened when Charlie temporarily takes over as acting Mayor and Paul becomes addicted to Carter's nicotine gum. |
| Guest Cast and Crew : Roy Firestone | Jack Knight | Scott Wolf | Director : Ted Wass | |
| Air Date : May. 09, 2001 | Rating ➦ ★★★★★★★★ |
| Episode 21 - [Brotherly Love] |
| Details : 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. |
| Guest Cast and Crew : Scott Wolf | Director : Ted Wass | Writer : Hadley Davis | Writer : Bonnie Schneider | |
| Air Date : May. 16, 2001 | Rating ➦ ★★★★★★★★ |
| Episode 22 - [A Shot In The Dark Part 1] |
| Details : Charlie and Caitlin fight as she plans to go to the Caribbean for a week with Tim on the night of a police ride-along. On the ride-along Charlie is shot...by Paul. Charlie fakes the severity of his injury to get Caitlin's attention. Charlie and Caitlin almost kiss but Tim interrupts. Meanwhile Carter and Stuart worry that they bicker like an old married couple and the Mayor hires an old prep school buddy who is now a bum. |
| Guest Cast and Crew : Kelly Monaco | Jack McGee | Scott Wolf | Adam Wylie | Director : Ted Wass | |
| Air Date : May. 23, 2001 | Rating ➦ ★★★★★★★★ |
| Episode 23 - [A Shot In The Dark Part 2] |
| Details : Charlie and Caitlin double date with Tim and Charlie's crazy ex. However Tim dumps Caitlin who calls Charlie to come over. They kiss; he freaks out and just wants to be friends but reconsiders and shows up on her doorstep later. The mayor remembers why he and Chad didn't get along in the first place. |
| Guest Cast and Crew : Vanessa Marcil | Scott Wolf | Jenna Fischer | Chad Cox | Serah D'Laine as Jenny | Director : Ted Wass | Writer : Tim Hobert | |
| Air Date : May. 23, 2001 | Rating ➦ ★★★★★★★★ |