Overview
Paul's cheap dentist puts braces on James instead of removing his infected tooth, causing problems in James' date with the new mail girl. The city's raffle to raise money for the Big Buddy program is screwed up when Paul skimps on the raffle tickets. Stuart and Carter blackmail Caitlin to decrease their workload.
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4 - 1Catcher in the Bronx September 21, 1999
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4 - 2James and the Giant Speech September 28, 1999
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4 - 3All the Mayor's Men October 05, 1999
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4 - 4These Shoes Were Made for Cheatin' October 12, 1999
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4 - 5Rebel Without a Chair October 19, 1999
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4 - 6The Mayor May Not November 02, 1999
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4 - 7The Great Debate November 09, 1999
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4 - 8How to Bury a Millionaire November 16, 1999
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4 - 9The Thanksgiving Show November 23, 1999
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4 - 10The Doorman Always Rings Twice November 30, 1999
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4 - 11Mustang Mikey December 07, 1999
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4 - 12My Dinner with Caitlin (a.k.a. Christmas 1999) December 21, 1999
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4 - 13A Tale of Two Sisters January 12, 2000
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4 - 14Casino February 02, 2000
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4 - 15The Marry Caitlin Moore Show February 09, 2000
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4 - 16Suffragette City February 16, 2000
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4 - 17Mike's Best Friend's Boyfriend February 23, 2000
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4 - 18The Pig Whisperer March 08, 2000
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4 - 19Uneasy Rider March 22, 2000
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4 - 20About Last Night April 19, 2000
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4 - 21Don't Get on the Bus April 26, 2000
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4 - 22Airplane! May 03, 2000
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4 - 23An American Deputy Mayor in Paris May 10, 2000
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4 - 24The Commitments May 17, 2000
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4 - 25Goodbye (1) May 24, 2000
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4 - 26Goodbye (2) May 24, 2000