Born in Miami, Florida, Bobby Allison got his career started at age 17 while still in high school. Although he was from Miami, he became a member of the “Alabama Gang” after the success of countless wins in Alabama along with Donnie Allison and Red Farmer. Bobby Allison went on to become the most successful driver of the gang and retired with 84 wins and one Cup championship.
He is the oldest driver to win the Daytona 500, winning the race at age 50. Owing to a successful career, Allison was inducted into NASCAR’s Hall of Fame in 2011. Nowadays, the retired Bobby is promoting rail safety for the “Keep on Living” campaign.
Jeff “The Mayor” Burton- 306 Races
In 1988, Jeff Burton began his racing career in the Busch series. He drove a car owned by his father, number 69. His first win happened nearly 10 years later in 1997 when he won the Interstate Batteries 500 at Texas Motor Speedway. Jeff Burton has had 21 wins in the NASCAR Sprint Cup Series.
His most memorable NASCAR moment was when he won at the Coca-Cola 600s in 1999 and 2000. Nowadays he seldom races, but like many other former racers, he’s never too far from the tracks. He works as a sports commentator for NBC Sports in their NASCAR coverage.
Matt Kenseth- 181 Top-Five Finishes
Matt Kenseth developed an interest in cars when he was just 13 years old after his father bought him a car. In 1988, 16-year-old Matt Kenseth started stock car racing at Madison International Speedway. 29 years later, the racer retired from full-time racing.
During his full-time career, he competed in 288 races for the NASCAR Xfinity Series and 665 races for the Monster Energy NASCAR Cup Series. He led over 11,756 laps and had over 300 top 10 finishes. Outside of NASCAR, Kenseth is a huge fan of the heavy metal band Metallica and is also a diehard supporter of the Green Bay Packers.
Tim Flock- 37 Pole Positions
Born into a famous stock car racing family, Tim Flock made a name for himself as a NASCAR racer. His racing career spanned from 1949 to 1961, during which he won 39 races, made 187 starts and had 37 starts in the pole position. Although his winning percentage was only 21 percent, in the racing world this is actually very impressive and high.
In fact, it’s the best winning percentage ever. For this reason, and a good reason, Flock was inducted in the NASCAR Hall of Fame in 2014. Flock, unfortunately, didn’t live to see this honor, as he passed in 1998 from liver and throat cancer.
Tony Stewart- 49 Wins
Every sport needs bad boys for some extra drama and entertainment. Tony Stewart, AKA “smoke” was one of NASCAR’s “bad boys.” He won three Cup championships in 2002, 2005, and 2011. Noted for his fearless and sometimes reckless driving as well as attitude problems, Stewart is the only person to win both a championship in NASCAR and IndyCar.
Stewart got his start in competitive go-karting and won his first championship at the age of 8. Stewart won at least once in every season that he raced. In 2011, Stewart won the Cup as both an owner and driver from Stewart-Haas Racing. He threw in the towel in 2016, having competed in 96 races over 14 years.