1. 1937 Cadillac Phaeton 5859
The Cadillac Phaeton 5859 is the epitome of a classically styled car. The custom built beauty was — and still is — a sight to behold, although it was out of the price range of most customers when it debuted during the Great Depression. The Phaeton 5859 was primarily designed from blueprints sketched by designer John Hampshire, and it went on to inspire the design of one of Cadillac’s concept cars from the 2010s. That this car’s style lead to the creation of a concept that came nearly 75 years after it speaks to how outstanding the Phaeton 5859 is. This one of a kind car sold for $962,500 at auction.