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.
s04e01 - Catcher in the Bronx
s04e02 - James and the Giant Speech
s04e03 - All the Mayor's Men
s04e04 - These Shoes Were Made for Cheatin'
s04e05 - Rebel Without a Chair
s04e06 - The Mayor May Not
s04e07 - The Great Debate
s04e08 - How to Bury a Millionaire
s04e09 - The Thanksgiving Show
s04e10 - The Doorman Always Rings Twice
s04e11 - Mustang Mikey
s04e12 - My Dinner with Caitlin (a.k.a. Christmas 1999)
s04e13 - A Tale of Two Sisters
s04e14 - Casino
s04e15 - The Marry Caitlin Moore Show
s04e16 - Suffragette City
s04e17 - Mike's Best Friend's Boyfriend
s04e18 - The Pig Whisperer
s04e19 - Uneasy Rider
s04e20 - About Last Night
s04e21 - Don't Get on the Bus
s04e22 - Airplane!
s04e23 - An American Deputy Mayor in Paris
s04e24 - The Commitments
s04e25 - Goodbye (1)
s04e26 - Goodbye (2)
In New York's City Hall, Mike Flaherty, the deputy mayor, has to protect the slightly moronic mayor, Randall Winston from those who want to ruin his political career, and from himself, cause he is constantly making an ass of himself and Mike has to try and make sure that his little escapades are either not made public or have very little negative effect on the mayor. Helping Mike is Carter, probably the least quirky member of the mayor's staff and Nikki and James. Stuart and Paul are two members of the staff who cause just as much problems. Mike's secretary, who joined the show during the second season was Stacy. Mike's girlfriend during the first season was Ashley, but the character was dropped, his next girlfriend, during the following season was Laurie, and during the third season it was Nikki, and in the fourth season it was Caitlin Moore, the mayor's campaign manager. Michael J. Fox would leave the show after the fourth season. During the next season, the new deputy mayor would be Charlie Crawford.