Known as the "Silver Fox", he debuted on the Grand National racing circuit in 1960 and earned Rookie of the Year honors that same season. He went on to win the NASCAR Championship in 1966, 1968 and 1969. Pearson ranks as one of the greatest of all NASCAR drivers and his duels with Richard Petty are legendary. Between August 8, 1963 and June 12, 1977, they finished one/two on sixty-three occasions, with Pearson coming out on top with thirty-three victories. Their most famous encounter came at the 1976 Daytona 500 when the two were running bumper-to-bumper on the final lap. They slammed hard against each other's front fender and both hit the wall. Petty's damaged car spun off the track just twenty-five yards from the finish line and the engine quit running and he could not get it to restart. All Petty could do was sit in his famous #43 and watch as Pearson's wrecked #21 limped across the finish line to claim victory.
Pearson won the "Most Popular Driver" award in 1979 and 1980. After twenty-six seasons in racing, he retired in 1986. He finished his career in second place behind Richard Petty on NASCAR's all-time win list with 105, and second in all-time pole positions. Considering his 105 wins, it should be noted that while driving for the Wood Brothers, the team ran only selected races throughout the season.
- In 1990, Pearson was inducted into the International Motorsports Hall of Fame.
- He was named one of NASCAR's 50 Greatest Drivers in 1998.
- He was inducted in the Motorsports Hall of Fame of America in 1993.