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Tim Bennett was raised in Detroit, Topeka, Hobbs, and Phoenix.
At age 12, he sold his first joke to The National Enquirer.
He attended Central High School and played bass in The Flatworms alongside singer/songwriter Andrew Creighton.
Bennett studied at the University of Arizona, where he performed in a college sketch comedy group that included members such as Graham Elwood, Paul Goebel, Michael Hartigan, Peter Murrieta, Jim Bruce, John Patrick Nelson, Bob Rubin, Timothy Gassen, Marlowe Weisman, Ted Sroka, Nicole Randall Johnson, Alex Baze, and Micah Wright.
In the early 1990s, he worked at The Second City in Chicago in various roles including box office staff, archivist, home theater installer, stage manager, assistant director, creative consultant, and as a writer and director of short films and TV pilots for the improvisational theatre.
His initial Hollywood appearances were as background talent on Melrose Place (1992) and Party of Five (1994).