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He played Skip Skiperton, an eccentric software tycoon, in the little-seen comedy. Many more would see Lee in his next picture, the 1970s rock-star epic Almost Famous. "Most of the meager charms of the chaotic romantic farce, " wrote New York Times critic Stephen Holden, "spring from the deft comic contortions of Hollywood's ultimate nerdy sidekick, Jason Lee. His attempts to reverse his karma are aided or thwarted by his dense brother, Randy (Ethan Suplee, who had a small role in Mall-rats ).
Indie-rock video director Spike Jonze cast him in the video for "100 percent, " a song by New York City alt-rockers Sonic Youth.
Actor in films, including: Mi vida loca—My Crazy Life , 1993; Mallrats , 1995; Chasing Amy , 1997; Enemy of the State , 1998; Kissing a Fool , 1998; Dogma , 1999; Mumford , 1999; Almost Famous , 2000; Vanilla Sky , 2001; Jay and Silent Bob Strike Back , 2001; Heartbreakers , 2001; Stealing Harvard , 2002; Dreamcatcher , 2003; A Guy Thing , 2003; Jersey Girl , 2004; The Incredibles (voice), 2004; The Ballad of Jack and Rose , 2005; Drop Dead Sexy , 2005; Monster House (voice), 2006; Clerks II , 2006.
Retired from his career as a professional skateboarder, Lee was initially reluctant to take the small-screen job when it was offered to him, having carved out a solid niche as a film actor with memorable roles in such movies as Mallrats and Vanilla Sky.
His next project was in another film by Smith, Chasing Amy , in which he played Banky Edwards, best friend to Ben Affleck's Holden Mc Neil.
The pals' comic-book authorship success and friendship is threatened thanks to Holden's crush on Joey Lauren Adams's character, who may or may not be gay.