Photo Credit: Barrett-Jackson

Tied with the previous Boss is this deliciously black 2008 Shelby GT500KR, or more specifically, GT500KR number one. This car marked the return of the KR moniker and debuted at a time when the country was crazy for Shelby Mustangs new and old. That helped push this car to a sold price of $550,000 at Barrett-Jackson’s 2008 Scottsdale auction, as did the charity aspect with all proceeds from the sale going to the Juvenile Diabetes Research Foundation.