Born into a motorcycle racing family, Bostrom is the son of Dave Bostrom and the nephew of Paul Bostrom, both accomplished dirt track racers. He began his own career in the same discipline, winning the AMA 600 Dirt Track National Championship in 1993. He moved onto road racing circuits in 1995.
His brother Eric Bostrom is also a professional motorcycle racer.
Bostrom made an immediate impact in AMA road racing. In 1998, riding for Honda, he won the AMA Superbike national championship without winning a single race during the season — a statistical rarity that spoke to his consistency across the full campaign. The following year, racing a Ducati in the domestic series, he visited Laguna Seca Raceway as a World Superbike wild card and won one race and finished second in another, signalling that his abilities extended beyond the domestic stage.
After his World Superbike stint from 2000 to 2002, Bostrom returned to American Honda for the domestic AMA Superbike Championship in 2003 on the RC51, then stayed for 2004 on the brand new CBR1000RR Fireblade, finishing fourth in the standings in both years. He later partnered Neil Hodgson at Ducati for the 2006 AMA Superbike Championship, before Ducati's withdrawal from the series at season's end prompted a move to Yamaha.
In 2007, Bostrom joined the Graves Motorsports Yamaha team for a rebuilding season in AMA Superstock, finishing second in points. The following year he switched to the Supersport class and led Graves Motorsports to the AMA Supersport Championship, his second national crown. At the 2009 season opener — the Daytona 200 — he won the 600cc race while also contesting the full Superbike class on a 1000cc Yamaha.
Bostrom made his first full World Superbike season in 2000 on a factory Ducati. The 2001 campaign was a genuine revelation: riding a factory L&M Ducati, he won six races — including five consecutive victories — to finish third in the final championship standings. It stood as one of the more eye-catching single-season performances by an American in the series. However, 2002 brought a sharp decline; he failed to win and results worsened progressively across the season.
He made one further attempt at the world stage in 2005 with the Renegade Honda team, but struggled throughout. He qualified slowest of the 28 international entries at the Qatar season opener and managed only scattered top-ten finishes, ending the year fourteenth overall.
In 2011, Bostrom made his MotoGP class debut as a wildcard entry at the United States Grand Prix, riding a Honda for the LCR Team. At 37 years old, he became the oldest rider to make their MotoGP-class debut in the modern era.
Beyond two wheels, Bostrom competed in AMA Supermoto, winning the AMA Supermoto Championship in 2003 and taking the gold medal at the inaugural X-Games Supermoto event — a field that included European Supermoto Champion Eddy Seel and supercross legend Jeremy McGrath. He won despite nearly crashing with five laps remaining.
In 2014, Bostrom was part of a four-man team that won the Race Across America cycling relay event, competing alongside Dave Mirra, Micky Dymond, and Dave Zabriskie.
Bostrom's 2001 World Superbike season remains the peak of his international career, and his three AMA national titles across Superbike, Supersport, and Supermoto illustrate his adaptability as a racer. His Laguna Seca wildcard performances in 1999 demonstrated that he was capable of competing with the best in the world on specific circuits. He is remembered as one of the more exciting American motorcycle racers of his generation, combining natural attacking speed with a willingness to compete across multiple disciplines.