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. Kimmel left Win Ben Stein's Money in 2001 and was replaced by comedian Nancy Pimental, who was eventually replaced by Kimmel's cousin Sal Iacono. The Man Show's success allowed Kimmel, Carolla, and Kellison to create and produce, under the banner Jackhole Productions, Crank Yankers for Comedy Central (on which Kimmel plays the characters "Elmer Higgins", "Terrence Catheter", "The Nudge", "Karl Malone" and himself) and later The Andy Milonakis Show for MTV2. 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.
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