20. Shelby GT – $600,000
Back in 1966, Shelby teamed up with Hertz rental company to make 1000 black and gold GT350 fastbacks. Pretty soon, GT350 H was a legend among the people looking to rent a race car, race it through the weekend and return it on Monday. There were reports of vehicles returned with race numbers on the side and the holes drilled to install race roll cages (via Motor Trend).
Eventually, Hertz stopped offering sports cars, but the legend was born. 41 years after the original GT350 H, Shelby introduced the GT model. The first one of those new Shelby GTs was offered for sale at the Barrett-Jackson auction in 2007, and it fetched a whopping $600,000, with all of the funds going to Carroll Shelby’s Children’s Foundation.