17: Jeff Gordon
There aren’t a lot of names that resonate with racing as much as Gordon’s does. He went from relative obscurity to becoming one of the most popular drivers of all time. After a lengthy career, what’s a NASCAR star to do? Well, for Gordon, it meant becoming a top executive at Hendrick Motorsports and announcing on NASCAR TV. Both career choices have become highly lucrative for the retired stock car racer.

Gordon was always a people person, and his outgoing personality made him an instant star. Although Gordon misses the limelight and the adrenaline rush, we’re sure he is happy to retire from the grind. Elite racing is intense motorsport with a lot of danger and risk, something that doesn’t equate to pleasant golden years.