In 1998, Starr made his Truck Series debut driving the No. 9 Chevrolet Silverado for Reher-Morrison Racing in five races. His best finish was an eighteenth at his home track at Texas Motor Speedway. The following season, he competed in the Truck Series full-time. Driving primarily for Tagsby Racing, he also competed for Team 23 Racing, Conely Racing, Morgan-Dollar Motorsports, and McGlynn Racing, and was able to finish 22nd in the standings. Sagby closed its doors at the end of the season, leaving Starr without a full-time ride. He drove most of his races for Conely part-time, as well as for Ware Racing Enterprises and TKO Motorsports, his best finish twelfth at Texas, where he also qualified on the outside pole. That season, he made his Busch Series debut at Talladega for Day Enterprise Racing, finishing 42nd. After running one race for TKO at Daytona International Speedway, he ran four races for Team Menard, finishing no lower than seventh.