Bowyer began racing at age five in motocross. Over the next eight years, he racked up more than 200 wins and numerous championships. He began street stock racing at Thunderhill Speedway, Mayetta, Kansas in 1996. He took home the Modified championship there in 2002. Bowyer won 18 races and placed 32nd in the Modified race at the Thunderhill Speedway in Mayetta, Kansas. He also captured the 2001 Modified championships at Lakeside Speedway (Kansas City) and Heartland Park Topeka. In 2002, he began racing in the NASCAR Weekly Racing Series, having 9 poles as well as 12 wins and 32 top five finishes on his way to a second-place finish the NASCAR Weekly Racing Series national points standings. He also was named the 2002 NASCAR Weekly Racing Series Midwest Champion following a second Modified championship held at Lakeside Speedway and a Late Model championship at the famed I-70 Speedway in Odessa, Missouri, his first attempt to race on asphalt.In 2003, Bowyer raced a full season in the NASCAR AutoZone Elite Division Midwest Series with a top-ten finish in his 11 races. Bowyer also made his first ARCA races in 2003 and caught the eye of famous car owner Richard Childress after leading 47 laps and placing second in his debut at Nashville Superspeedway driving for Scott Traylor from Kansas City.After the second-place finish, Childress called Bowyer by phone and offered him a job. Bowyer believed he was making fun of him and then hung up. Childress called back soon afterward and with a not-too-happy tone he still made an offer to Bowyer
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