The Bugatti Veyron is up there in the "You don't need a car this expensive, you only bought it because you couldn't think of anything better to do with your excess money" category. Ask this again if Apple gets into the industry.
1. 1936 Bugatti Type 57C Atlantic - $43.7 million (2010) Head and shoulders above all of the cars in the list. It is so rare that only three examples plus their prototype were ever built. This buyer was anonymous but Ralph Lauren is one of the other two very lucky owners.