Like many American road race champions, Bostrom hails from a family of successful dirt-track racers, and launched his career in the same fashion by winning the AMA National 600 Dirt Track Championship in 1993. Early road racing successes include the 1998 AMA Superbike title, a win as a wildcard at the 1999 Laguna Seca World Superbike round, and 6 wins as a full time World Superbike rider in 2001 aboard a factory Ducati. Returning to the AMA, Bostrom took the 2008 Supersport title with the Graves Motorsports Yamaha team. His MotoGP debut came at age 37, where he contested the Laguna Seca round on Toni Elias\' second bike, lapping quicker than the full time rider, though he retired from the race.