[2] He became a late model champion at Berlin Raceway in Marne, Michigan before joining the American Speed Association (ASA) in 1990.

In 1993, Benson made his Busch Series debut at Michigan International Speedway, driving the No.

He won his first career race at the SplitFire 200 and finished sixth in points, winning Rookie of the Year honors.

He failed to qualify for one race at the Food City 500, but won the 1996 NASCAR Winston Cup Rookie of the Year title.

In August, he dominated the Brickyard 400 before a problem on the last pit stop ended his chances for victory.

He won his second career pole at Michigan and finished outside of the Top 10 by one point to Ken Schrader.

At the start of the 2000 Winston Cup season, Benson found himself without a sponsor when he signed on to join Tyler Jet Motorsports to run the No.

During the race, Benson and crew chief James Ince gambled on a late pitstop when they took only two right side tires and fuel, to come out with the lead with 43 laps to go.

Benson finished sixth in the third race at the Las Vegas Motor Speedway, and was eleventh in points.

On November 3, he started 26th in the 43 car field at the Pop Secret Microwave Popcorn 400 at Rockingham.

Valvoline decided to release Benson in favor of rookie driver Scott Riggs after the season was over.

2004 started off with Benson signing on with Phoenix Racing to run the full 2004 Busch Series schedule.

Benson won his first and only career Busch pole at Rockingham, but a rules violation relegated him to last place when the green flag dropped for the race.

He was poised to win at Bristol in the spring until Benson was caught up in a late race incident between Kevin Harvick and David Stremme.

Over the next few months Benson ran one Busch race for Matt Kenseth and Robbie and John Reiser.

He won his first Craftsman Truck Series race at the 2006 Con-way Freight 200 at the Michigan International Speedway.

Benson won his fifth race of the year at the Casino Arizona 150 at Phoenix International Raceway.

He finished the season in third place with four wins: the Toyota Tundra Milwaukee 200 at Milwaukee Mile, the O'Reilly 200 presented by Valvoline Maxlife at Bristol, the Missouri/Illinois Dodge Dealers Ram Tough 200 at Gateway International Raceway, and the Ford 200 at Homestead-Miami Speedway.

36 Toyota Camry in the Cup Series on the same weekend; he did so at the final two races of the year (Phoenix and Homestead-Miami).

In addition, to date he joined a list of only 6 drivers to ever win at least one championship in more than one of the three main title series (Bobby Labonte, Brad Keselowski, Kevin Harvick, and Kyle Busch are the others, and they have won championships in the second tier and Cup Series.)

His second, third, and fourth wins came at the Built Ford Tough 225 at Kentucky Speedway, the Power Stroke Diesel 200 at O'Reilly Raceway Park, and the Toyota Tundra 200 at Nashville Superspeedway.

27 Toyota Camry fell through, it was announced that Benson and Mike Skinner would share driving duties for the No.

On December 8, 2008, Benson announced that he would be joining the Red Horse Racing team to drive the No.

On June 13, 2009 Benson was burned in a fiery crash in an ISMA Supermodifieds race at Berlin Raceway.

[6] For the 2010 season, Kyle Busch Motorsports intended to field a truck for Benson, but did not to secure the necessary sponsorship.

Benson served as a mentor to Kyle Busch Motorsports' drivers Brian Ickler and Tayler Malsam.

Turn One Racing announced in 2011 that they intended to field a truck for Benson in 2012, but the deal fell through due to sponsorship issues.

[8] Benson is retired from NASCAR, but still races a supermodified for car owner Brad Lichty on the ISMA tour.

In 2023, Benson was announced as a competitor for the SRX Series in a one-off appearance at Berlin Raceway.

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