The Mayor of New York City needs the help of his staff, especially his Deputy Mayor, to keep the media off his back and make sure things are running smoothly.
Charlie Crawford (Charlie Sheen) spends his first day in office as New York City's Deputy Mayor. The Mayor has trouble adjusting to office life without Mike. (S5, E01)
Randall needs dental work, but his long-time dentist drops dead during the procedure. Carter & Stuart deal with a bike messenger who keeps stealing their parking spot. (S5, E02)
Thanks to Caitlin's meddling, the press discover that Charlie never graduated school due to a missed exam. Stuart is jealous of Carter's friendship with Caitlin. (S5, E03)
Caitlin makes an appearance as a guest host on a talk show. The Mayor takes a much-needed holiday. Stuart and Paul are put in charge of an archaeological dig. (S5, E04)
In need of a religion refresher, Randall and Charlie accidentally wreak havoc on Claudia's religious education class and her future. Caitlin has a personality crisis. (S5, E05)
The staff's hastily-made float goes awry at the Thanksgiving parade. Paul convinces his mother that he is dating Caitlin, so she won't be upset that Claudia left him. (S5, E06)
Charlie's one-night stand with Caitlin's yoga friend Samantha doesn't go the way he planned. Carter, Stuart and Paul compete for a trip to New Orleans with the mayor. (S5, E07)
An overworked Charlie beats Mayor Winston at racquetball, crushing his ego in the process. Paul campaigns to get a raise. Stuart hires an actor to go out with Carter. (S5, E08)
Randall, Carter, and Charlie try their hand at working in a fast-food restaurant. Stuart tries to impress new secretary Angie by posing as a biker. (S5, E09)
Paul struggles to find the best joke for the mayor's Christmas card. The mayor's attempt to be more involved at the office backfires. (S5, E10)
Paul moves into a college dorm room. Charlie sets up Caitlin on a blind date with a bumbling optimist. Randall tries to make amends after parking in a disabled spot. (S5, E11)
The Mayor's new girlfriend clashes with Charlie over who should write an upcoming speech. Carter and Stuart brawl during a hockey game. (S5, E12)
Paul, Carter, and Stuart goad Charlie into playing poker with them, not knowing that he is a reformed gambler. Caitlin helps the Mayor become more self-sufficient. (S5, E13)
Charlie calls a college buddy to defend Randall in a lawsuit after he ruins a model's coiffure at a charity fashion show. Carter coaches Paul in the art of wooing. (S5, E14)
Caitlin hires an image consultant to determine why the Mayor's approval rating with women has plummeted. Stuart's past comes back to haunt him. Guest stars Rosie O'Donnell. (S5, E15)
Charlie gets trapped in a stalled train before his date with a woman he's desperate to impress. Carter's weird neighbour Kurt hits on him. (S5, E16)
To the Mayor's horror, his visiting daughter Meg makes some big life changes. Charlie blows off a date with Julia to attend a sporting event with Stuart, Carter & Paul. (S5, E17)
Charlie fulfills a dream of playing minor league baseball, but Caitlin intervenes in order to get him back to work. Randall receives a death threat from an unlikely source. (S5, E19)
The media's reaction to the Mayor's ex-wife's tell-all book leads to his humiliation & a press boycott. Caitlin dates a philanthropist who's turns out to be a sci-fi nerd. (S5, E20)
Charlie and Tim compete for Caitlin's affections. Carter hires his sister to work at City Hall and goes to extreme lengths to keep their relation a secret. (S5, E21)
Part 1: Caitlin & Charlie have their first real row. While on a police ride along, Charlie is shot. Carter and Stuart's friendship takes the next step. (S5, E22)