27) Dale Jarrett
The Daytona 500 is NASCAR’s answer to the Super bowl, so it’s a pretty big deal. For any stock car driver, this is the dream. Jarrett not only won this trophy, but he won it on three occasions. These victories make up a small fraction of his 32 career wins in the Cup Series, putting him inside the top 25. Jarrett comes from a big racing family and was able to carve out his own legacy, despite still being overshadowed by his father- who we will learn about later.
26) Rex White
White was inducted into the NASCAR Hall of Fame in 2015 and was an early star in the Cup Series, racing from 1956 to 1964. In only 233 starts, he was a constant presence at the top of the leaderboard and won 28 times. Additionally, he finished in the top five almost 50% of the time, and in the top ten nearly three-quarters of the time. He won the Cup Series in 1960, impressively surpassing other top drivers like Richard Petty, Ned Jarrett and Junior Johnson.