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- Season 4 overviewSep 21, 1999-May 24, 200026 episodesSeason 4 episodes1. Catcher in the Bronx Sep 21, 1999
- Mike must hire a campaign manager for the Mayor's Senate run.
- 2. James and the Giant Speech Sep 28, 1999
- Caitlin tries to fire James and take over his speech-writing duties; guest Nipsey Russell.
- 3. All the Mayor's Men Oct 5, 1999
- Mike plans an internal break-in to obtain background files on staffers at City Hall.
- 4. These Shoes Were Made for Cheatin' Oct 12, 1999
- Mike tricks Nikki into going into couples counseling; the mayor is challenged by eighth-graders.
- 5. Rebel Without a Chair Oct 19, 1999
- An interviewer for a gay magazine misinterprets Mike's comments about his closeness to the mayor.
- 6. Mayor May Not Nov 2, 1999
- Former Sen. Alfonse D'Amato advises Mayor Winston, who considers giving up his bid for the Senate.
- 7. The Great Debate Nov 9, 1999
- Mike targets a wealthy political donor (Amy Irving) to help the mayor's bankrupt Senate campaign.
- 8. How to Bury a Millionaire Nov 16, 1999
- The mayor falls into an adjacent pit during a rescue operation to free a trapped baby.
- 9. The Thanksgiving Show Nov 23, 1999
- Mike and Caitlin pose as a couple to win an endorsement for the mayor.
- 10. The Doorman Always Rings Twice Nov 30, 1999
- Mike deals with an angry doormen's union; Paul opens a politically themed restaurant.
- 11. Mustang Mikey Dec 7, 1999
- Mike and Caitlin take the mayor's convertible for a joy ride.
- 12. My Dinner With Caitlin Dec 21, 1999
- Mike invites Caitlin to his Christmas party but doesn't expect her to bring a date.
- 13. A Tale of Two Sisters Jan 12, 2000
- Mike goes on a date with Caitlin's sister; Stuart takes up art.
- 14. Casino Feb 2, 2000
- Mike must raise $500,000 when a ticket glitch in a raffle results in hundreds of winners.
- 15. The Marry Caitlin Moore Show Feb 9, 2000
- Mike hires a British director for the mayor's political advertisements.
- 16. Suffragette City Feb 16, 2000
- Caitlin's new romance with her ex-husband bothers Mike; Carter exposes anti-gay discrimination.
- 17. Mike's Best Friend's Boyfriend Feb 23, 2000
- Mike suspects Carter's new boyfriend is coming on to him; Paul tries to impress a reporter.
- 18. The Pig Whisperer Mar 8, 2000
- Angry farmers protest the mayor's latest proposal; Stuart's girlfriend had a fling with Paul.
- 19. Uneasy Rider Mar 22, 2000
- Mayor Winston seems unaffected by his father's death; James believes Caitlin is attracted to him.
- 20. About Last Night Apr 19, 2000
- The staffers drown their sorrows in a bar while the president visits the mayor.
- 21. Don't Get on the Bus Apr 26, 2000
- Sparks fly between Mike and Caitlin during the mayor's listening tour.
- 22. Airplane! May 3, 2000
- Mike continues to pursue Caitlin despite her engagement; Carter heads a hunger strike.
- 23. An American Deputy Mayor in Paris May 10, 2000
- Mike pursues Caitlin to Paris to declare his love before she marries Trevor.
- 24. The Commitments May 17, 2000
- Mike tries to prove that his attraction to Caitlin goes beyond the physical level.
- 25. Goodbye May 24, 2000
- Mike decides to take the fall for a mob scandal in order to protect the mayor.
- 26. Goodbye May 24, 2000
- Mike Flaherty (Michael J. Fox) leaves City Hall and his job as deputy mayor.