8. Mercedes-Benz 540K Spezial Roadster

Years Of Production: 1936-1940
Cost: $8,200,000
Famous Owners: William Randolph Hearst, Bernie Ecclestone
Complex Says: After WWII, motoring changed. The designs of high-end cars shifted away from exuding the kind of elegance that the $540,000 Spezial Roadster does. Taking this as your ride of choice will not just prove that you have more than $8 million in disposable income. It will make you look like your name should be preceded by "Baron von."