5. Duesenberg Model J

Years Of Production: 1928-1937
Cost: $1,000,000 to $4,400,000, depending on the engine
Famous Owners: Jay Leno, Al Capone, Gary Cooper, the Duke of Windsor, Prince Nicholas of Romania, Queen Mary of Yugoslavia, King Victor Emmanual III of Italy, King Alfonso XIII of Spain
Complex Says: There was once a time when the most technically advanced luxury car in the world was made in Indiana. Everyone from Al Capone to Old World royalty loved the car for its power, speed, luxury, and intimidating Gothic styling. If Herman Munster was the emperor of Transylvania, he'd drive one of these.