Price: $16.39 million
Auction: Gooding & Company, Monterey, CA 2011

This 0666 TR is the first 250 Testarossa ever built. Unlike many other first models, however, this car has earned its worth. It boasts a very legit eight-year racing history at the world's most prestigious tracks and was piloted by the greatest names in motorsports. It must have been one hell of a bidding war, but this piece of automobile culture was worth every pretty penny.