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Terry Zwigoff began his film career accidentally in 1978, when he found a rare 1920s recording by an unknown Chicago blues musician. A musician and record collector, Zwigoff was so impressed by this old 78 that he began what was to become two years of detective work to discover who the artist was and what his life had been like. Louie Bluie, a documentary film which premiered at Sundance in 1985, was the result.

His second film Crumb, about the cartoonist Robert Crumb and his two brothers, was a complex meditation on family, art, success and failure. The film won virtually every award for documentaries in 1995, including the Grand Jury Prize at the Sundance Film Festival as well as citations from the New York and Los Angles Film Critics and the Directors Guild of America. Over 100 film critics hailed Crumb as one of the Top Ten Films of 1995.

Zwigoff turned to fictional features in 2001 with Ghost World, adapted from Daniel Clowes' comic book about two female teen misfits, played by Thora Birch and Scarlett Johanssen, and added an aging, antisocial record collector (Steve Buscemi) to the story. The film won AFI and Golden Globe awards for Buscemi and Birch, and a Best Adapted Screenplay Academy nomination for Zwigoff and Clowes. Ghost World appeared on over 150 Top Ten Lists for 2001.

He followed with the offbeat comedy Bad Santa (2003), which starred Billy Bob Thornton as a dissipated, womanizing crook posing as a department store Santa, executive produced by Joel and Ethan Coen . Thornton was nominated for a Golden Globe for his performance, and the film was highly praised and a commercial success.