Chicago, 1955: Hugh Hefner’s fledgling magazine Playboy – he was going to call it Stag Party but changed his mind – founded just two years earlier was a runaway success.

Having begged, borrowed and even mortgaged his furniture to get the magazine off the ground, Hef felt it was time to celebrate with a new Cadillac Eldorado.

In 1955 Hef felt it was time to celebrate with a new Cadillac Eldorado

Eventually he’d have a private plane staffed by gorgeous babes in skintight leather outfits, but the Caddy was one of the first real symbols of Hef’s success.

(Scrape up $1,300 and you can read all about it in his limited edition, six-volume autobiography from Taschen.)