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During this time he met and befriended a struggling comedian named Adam Carolla.Kimmel began his television career as the comedic counterpart to Ben Stein on the game show Win Ben Stein's Money, which began airing on Comedy Central in 1997.He suggested that if the Detroit Pistons defeated the Los Angeles Lakers, "they're gonna burn the city of Detroit down …and it's not worth it." Officials with Detroit's ABC affiliate, WXYZ-TV, immediately announced that that night's show would not air on the station.After this, Jimmy's sidekick, Guillermo, appeared in a spoof of The Bourne Ultimatum, which starred Damon.He was then chased down by Damon, who was cursing about Kimmel being behind all this., causing Kimmel to describe himself as "the three-headed dog the stars must pass on their way to No-Dancing Hell". So I just wanted to say, I'm sorry, I apologize.” Despite the apologies from ABC and Kimmel, protests continued.
Kimmel also produced and co-wrote the feature film Windy City Heat, Festival Prize winner of the Comedia Award for Best Film at the 2004 Montreal Comedy Festival.
In 1999, during his time with Win Ben Stein's Money, Kimmel co-hosted (with Adam Carolla) and co-produced (with Daniel Kellison), Comedy Central's The Man Show.