Hamilton quit school at the age of fourteen[2] and began his racing career at Nashville Speedway USA, now Fairgrounds Speedway, racing on the weekly circuit at the legendary track, where he won back to back Late Model Stock Car Championships in 1987 and 1988.

In 1988, Hamilton won an unprecedented four races, in three different divisions, in one night, at Nashville Fairground Speedway.

Hamilton began to be noticed within the NASCAR ranks after racing in a special four-car "Superstar Showdown" at Nashville in 1988 against Cup Series drivers Sterling Marlin, Darrell Waltrip, and Bill Elliott.

Hamilton made his NASCAR debut in the Busch Series in 1988 at Charlotte Motor Speedway driving the No.

He made his Winston Cup debut in a "Days of Thunder" car owned by Hendrick Motorsports.

He matched his 11th-place points finish in 1990 with Filmar Racing, when he was picked up by Tri-star Motorsports to run Winston Cup full-time beginning in 1991, driving the No.

68 Country Time Lemonade-sponsored Oldsmobile, posting four Top 10 finishes and narrowly defeating Ted Musgrave for Rookie of the Year.

He spent the rest of the season in the Cup and Busch Series, posting two Top 10s for Akins-Sutton Motorsports.

The next season, he finished a career-best ninth in the points standings and won his first race at Phoenix, the first for Petty Enterprises since 1983.

He then signed with Morgan-McClure Motorsports in 1998 and in their eighth race together, he won from the pole, leading 378 of 500 laps at Martinsville Speedway.

He posted three Top 10s in 2002 but suffered a broken shoulder late in the season, causing him to miss several races.

4 Dana Dodge Ram Hamilton picked up two wins in his first year on the circuit and finished sixth in points.

[5] He took part in the Craftsman Truck Series race that night, before starting therapy the following Monday.

51 and "Rowdy" decals, a tribute that Busch continues today in late model and truck racing.

Hamilton returned to the track for the race at Kentucky Speedway, overseeing his team's operations.