1954 Mercedes-Benz W196 Silver Arrow ($29.6 million; 14 made in total) (8/10)

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A car that was quite ahead of its time, calibrated with fuel injection, a 1954 Silver Arrow was recently sold at auction for $29.6 million. There are only 10 known to still exist. Adding to its worth is that the 1954 Silver Arrow was driven by the iconic Grand Prix champion Juan Manuel Fangio.

1955 Jaguar D-Type ($21.8 million) (7/10)

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