Mike makes the staff work on Oscar Sunday due to a screw-up of Paul's. The staff reminisces about their favorite movie moments to pass the time.

When Carter is unexpectedly called to a late-night meeting, Charlie's left in charge of entertaining Spencer, a 16-year-old boy whom Carter sponsors through the ""Big Brother"" program. Having already had a date planned, Charlie has no choice but to bring Spencer along for the ride. Meanwhile, the Mayor is racked with guilt which is causing him insomnia.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Mike prepares to have sex with Heidi Klum for the first time. After ""it"", Heidi asks Mike to keep their relationship a secret. James receives his Aunt Sarah's ashes in the mail; his Aunt Sarah was a cow. Mike daydreams while making a statement to the press and accidentally reveals his relationship with Heidi; she breaks up with him. Paul's new fan creates problems for Aunt Sarah (take a wild guess).

Carter, Nikki and Mike go deer hunting in a fundraising attempt. While Mike is gone, Stuart becomes Stacy's boss for the day. And, with Claudia's help, Paul campaigns for a raise.

Mike discovers that his childhood pal, Nate Scott, has more in common with Carter than meets the eye, and finds it difficult to deal with this revelation. Meanwhile, Paul instructs Stacy in the finer art of being a cheapskate.

Paul has moved to Harlem and is annoying Carter and Janelle because he thinks that he's black. The Mayor is preparing to run the Olympic torch around City Hall, but can't because the Nigerian speed walker supposed to deliver the torch to him has disappeared, lost in the city. Mike struggles with the fact that he can't live without his job, while trying to take a vacation. Nikki finds a ringer to pose as her boyfriend, for them to have dinner with Mike. Stacy spills the beans to Mike about Nikki's feelings for him.

Stacy's staying with Carter and Stuart while her apartment is fumigated. Her partying cramps their style. Trying to outdo NASCAR driver Jeff Gordon and NBA player Jayson Williams, the Mayor promises his kidney to a young boy. Unfortunately, his doesn't match--but Mike's does. Meanwhile, Mike's playing the jealousy game with Nikki and promises to donate his kidney to the boy in hopes that she'll break up with Arthur for him. But when she offers him a chance to speak up about his feelings, he's anesthetized for his surgery and can't say anything.