Benson was born 27 June 1963 in Grand Rapids, Michigan. He is the son of Johny Benson, Sr., who competed in on Winston Cup race in 1973.

Johnny, Jr. was the 1993 American Speed Assn (ASA) champion. He was in his first Busch Series race in 1993 and won the 1995 championship race despite winning only 2 races that season. Following this, he moved to the Winston Cup in 1996 and was named Rookie of the Year. He placed 11^th in points and again in 2001 and won his first Winston Cup race in 2002 at the North Carolina Speedway race. He was dropped from his team after the 2003 season to appease the team sponsor Valvoline. He has run part-time in the Nextel Cup, the Busch Series and others.