NASCAR Winston Glass Rookie of the entire year in 1996, won championships in the Busch and Craftsman Pickup truck Series. He raced in the American Speed Association, making its First year of the entire year award in 1990. After becoming a member of the Craftsman Pickup truck Series, he was called Most Popular Drivers from 2006 through 2008. His dad John Benson, Sr. drove in a number of modified trips. He was leading the 2000 Daytona 500 with 4 laps to visit before he was handed by race champion Dale Jarrett.