1933 Ford Three-Window Coupe (Jeff Gordon)

You can’t mention NASCAR without mentioning the name Jeff Gordon. He was one of the most decorated drivers in NASCAR history. His unique approach to racing and fan relations helped cultivate the future of the sport. But Gordon also has a massive net worth and he has spent a considerable part of that money on custom cars (via Motor Trend).

His most notable acquisition is the 1933 Ford Three-Window Coupe. The Three-Window Coupe was one of the most notable Ford models ever built. Gordon owns an all-black one with a lot of chrome treatments and performance.