Bowyer began racing at the age of five in motocross. He went on to capture over 200 wins and numerous championships over the next eight years. In 1996, he began racing street stocks at Thunderhill Speedway in Mayetta, Kansas, and won the Modified championship there in 2000. Bowyer racked up 18 wins and 32 top-five finishes on his way to capturing the 2001 Modified championships at Lakeside Speedway in Kansas City, Kansas and Heartland Park Topeka. In 2002, he began racing in the NASCAR Weekly Racing Series, posting 9 poles, 12 wins and 32 top-five finishes en route to a second place finish in the NASCAR Weekly Racing Series national point standings. He was also crowned the 2002 NASCAR Weekly Racing Series Midwest Champion after another Modified championship at Lakeside Speedway and a Late Model championship at the famed I-70 Speedway in Odessa, MO, his first attempt at racing on asphalt.