Born and raised in Southern California, Jason Lee took up skateboarding at age 13. By 18 he was on the professional skateboarding circuit, where he wowed legions of young fans and popularized a move called the "360 flip." Inspired to tap into the commercial aspect of the sport, Lee and a friend started the twin companies Stereo Skateboards and Stereo Sounds Clothing. In the early 1990s, Lee took his tricks in front of the camera, appearing in several music videos - including one for the Sonic Youth song "100%," directed by Spike Jonze. Lee got his first taste of straight acting the next year, when he turned up alongside Jonze as a teenage drug customer in Allison Anders's Mi vida loca (1993).

Lee's movie career began in earnest when he landed a lead role in Kevin Smith's Mallrats (1995) (at his very first audition, according to Smith). While the film was almost universally panned, Lee received high marks from critics and audiences for his turn as "cynical sidekick" Brodie Bruce. Smith was so pleased with Brodie that he wrote a part for Lee in his next film, Chasing Amy (1997): Ben Affleck's cranky roommate and comic book partner Banky. Lee won an Independent Spirit Award for his performance.

After appearing in several indies and a made-for-TV movie, Lee crossed over into mainstream circles with Kissing a Fool (1998). Starring opposite David Schwimmer and Mili Avital, he played a writer who works through his last breakup by writing a book. In 1999, Lee landed two significant acting gigs: one as the demon Azrael in Kevin Smith's Dogma (1999), and another as the eccentric young billionaire Skip Skipperton in Mumford (1999). He then went to work on Cameron Crowe's Almost Famous (2000), in which he plays a member of the fictional '70s band Stillwater.