Price$27.5 million
Auction: RM Auction, Monterey, Calif 2013

Poor NART. How do you think it felt to sell for roughly $10 million more than the third place car and not be atop the charts? The original estimation for the car was about $14M and $17M, but it hit $16 mill on the second bid, so it was clear early on that this was going to be a special auction.

NART stands for North American Racing Team, and only 10 of these beautiful specimens were built. The Spider popped up in The Thomas Crown Affair in 1968. Canadian buyer Lawrence Stroll played an instrumental role in creating Tommy Hilfiger.