No. 5 – Fireball Roberts
Roberts came his closest to winning a NASCAR title in 1950 when he finished second in the final standings. Roberts won 33 races during his 15-year career. Of those 33 wins one was at the Daytona 500. Winning Daytona is an accomplishment all by itself and for some it might be the next best thing after winning a championship.
Roberts was also a two-time winner of the Southern 500. In 1998 Roberts was named to NASCAR’s list of the 50 Greatest Drivers, which was deserved. In his 206 career NASCAR races Roberts finished inside of the top-10 122 times. For those who can’t do complex math in your heads (much like myself), that means that Roberts finished inside of the top-10 in almost 60 percent of the events he raced in.