Season 5 (2000)

Hello Charlie
7.0

October 18, 2000 • 22m

Charlie Crawford is late for his first press conference as the new deputy mayor. He later runs into trouble trying to settle a tol...Read more

Smile
7.0

October 25, 2000 • 22m

Charlie tries to get the mayor to a dentist before an important photo shoot. Caitlin hires a new male assistant only because he's ...Read more

The Spanish Prisoner
7.0

November 1, 2000 • 22m

Caitlin causes a misunderstanding when she believes that Charlie is taking a Spanish class to improve relations with the Latin Ame...Read more

The Bone Collectors
7.0

November 8, 2000 • 22m

Caitlin auditions for the job of co-host on ""Live with Regis."" Stuart and Paul work together supervising after bones are discove...Read more

Blind Faith
7.0

November 15, 2000 • 22m

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...Read more

Balloons over Broadway
7.0

November 22, 2000 • 22m

Paul convinces his mother that he is dating Caitlin, so she won't be upset that Claudia left him. Charlie tries to prove to Caitli...Read more

Lost and Found
1.0

November 29, 2000 • 22m

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.

All the Wrong Moves
7.0

December 6, 2000 • 22m

An overworked Charlie causes problems after beating the mayor at racquetball. Paul's annual request for a raise is approved by the...Read more

The Burgers of Wrath
7.0

December 13, 2000 • 22m

Mike has been in Zimbabwe for three weeks, so Paul teaches Caitlin about celibacy. Stuart convinces Angie that he's a biker guy. W...Read more

Toy Story
7.0

December 20, 2000 • 22m

Paul struggles to find the best joke for the mayor's Christmas card. Carter convinces Caitlin to volunteer with him at a retiremen...Read more

The Perfect Dorm
7.0

January 10, 2001 • 22m

In an attempt to get over Claudia, Paul decides to move into a college dorm. Caitlin tries dating, after ending her relationship ...Read more

Hey Judith
7.0

January 17, 2001 • 22m

Caitlin sets the mayor up with her neighbor, Judith, who becomes way too much of an influence on the mayor. Carter helps Stuart pr...Read more

The Gambler
7.0

January 24, 2001 • 22m

Paul, Stuart and Carter rope reformed gambler Charlie into their poker night, and are responsible for his subsequent gambling bend...Read more

In the Company of Dudes
7.0

February 7, 2001 • 22m

When a supermodel sues the mayor, Charlie hires his old college friend to defend him. Charlie finds himself torn between two frien...Read more

The Image Maker
7.0

February 14, 2001 • 22m

Carter discovers an old love letter written by Stuart. He decides to set Stuart up with the addressee of the letter, a woman who t...Read more

Trainstopping
7.0

February 21, 2001 • 22m

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...Read more

Rain on My Charades
7.0

February 28, 2001 • 22m

The mayor's daughter Meg returns and inspires Caitlin to be more spontaneous and free. Paul, Stuart and Carter give Charlie advice...Read more

You've Got Male
8.0

April 25, 2001 • 22m

Stuart is hired to write a porno movie. Charlie and Caitlin compete for a donation from a wealthy male chauvinist. After Paul po...Read more

Minor League
8.0

May 2, 2001 • 22m

Charlie tries out for a minor league baseball team, trying to relive his high school glory days. Caitlin encourages the pitcher t...Read more

Science Friction
8.0

May 9, 2001 • 22m

Caitlin falls hard for a rich, young, sexy philanthropist. The Mayor is threatened when Charlie temporarily takes over as acting M...Read more

Brotherly Love
8.0

May 16, 2001 • 22m

Charlie attempts to interfere with Caitlin and Tim's burgeoning relationship. Meanwhile, Carter hires his sister to work at City ...Read more

A Shot in the Dark (1)
8.0

May 23, 2001 • 22m

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 rid...Read more

A Shot in the Dark (2)
8.0

May 23, 2001 • 22m

Charlie and Caitlin double date with Tim and Charlie's crazy ex. However, Tim dumps Caitlin, who calls Charlie to come over. The...Read more