Apparently, Hef named his empire after the recently defunct Playboy Automobile Company – and his interest in American cars doesn’t end there, as the picture above attests. But he’s also a big Mercedes fan: he’s known to have owned a 300 SL Roadster, as well as a pair of 600 Pullmans. The latter, rather unsurprisingly, came complete with champagne coolers, central partitions, rear privacy curtains and reclining rear seats.
With an eye for voluptuous curves, Hef would perhaps be instinctively drawn to an E-type, or maybe a pretty Ferrari Dino. Then again, there’s every chance he’d let his eccentric side run wild by choosing this Zimmer (no giggling at the back please) Quicksilver, coincidentally of the same vintage as his wife, Crystal.