[h=2]5. 1958 Cadillac Eldorado Brougham[/h] Source: Darin Schnabel/RM Sotheby’s

By 1958, the Continental had been returned to the Lincoln lineup. It was just as well, because that year Cadillac responded with the Eldorado Brougham, a $13,074 dream machine that was one of the most luxurious, exclusive, and advanced cars in the world. With space-age features like a self-leveling air suspension, power seats with memory, dual-level climate control, and cruise control, the Caddy was in many ways decades ahead of the competition. With only 304 cars built in ’58, it was the car to have in the late 50s. Sinatra loved them so much that he owned several, with one appearing alongside him in 1960s’ Ocean’s Eleven. Bonham’s sold one ex-Sinatra Brougham in 2009 for an undisclosed sum. It had been expected to fetch as much as $375,000.