1962 Ferrari 250 GTO Berlinetta ($38.2 million; 39 made in total) (10/10)

List item

Auctioned by Bonhams in 2014, the first 250 GTO to be sold in many years and one previously owned by the French Formula One great Jo Schlesser, sold for $38.2 million in Carmel, California. Why did it cost this much? The Gran Turismo Omologato is rated as one of the best Ferraris of all time, and this particular model—the Berlinetta—is one of the first cars to have disc brakes.

1957 Ferrari 335 Sport Scaglietti ($35.7 million) (9/10)

The Tasty Espresso Martini alternative: The Dominicana Cocktail (7/26)