NASCAR: The 14 Greatest Moments Of Tony Stewart’s Career

8. 1999 Winston Cup season

In 1999, Stewart started out as a nobody in the NASCAR world, with only a few impressive Xfinity Series races under his belt. But with the aforementioned second-place starting spot in his debut Daytona 500, the NASCAR garage was aware that this kid had speed. They just weren’t prepared for how much speed he actually showed in 1999.

Stewart went on to become the most successful rookie since Davey Allison in 1987. Aside from scoring a pair of poles at Martinsville and Bristol, he would score a grand total of five front-row starts in ’99. He would also win three races (Richmond, Phoenix, Homestead), 12 top-fives, and 21 top-10s. Those results netted him fourth-place in the final points standings, and he would go on to win the Rookie of the Year award.