One of the intimidating things about getting older is the realization that no matter what you do, one day, you’re going to end up as that poor schmuck on the wrong side of the generation gap. One day you’re the voice of a generation and the owner of the quickest-selling album of all time, the next you’re recording an album of ukulele songs. Unless, of course, you happen to be one of the ten people we’ve catalogued below, who have the irritating tendency to somehow get cooler as they get older. Some of them started out as massive dorks, mind. Read on after the jump.
Forty-five years ago, David Bowie was a somewhat fey, paisley-shirted singer/songwriter preparing to record a dreadful novelty song called “The Laughing Gnome.” But by the time the 1970s rolled around, he was well on the way to being the coolest man alive, and apart from Tin Machine, a curious flirtation with drum ‘n’ bass, and that video with Mick Jagger, he’s barely put a foot wrong since – through Ziggy Stardust to Aladdin Sane, the Thin White Duke and beyond. These days, he’s got the suave elder statesman role nailed down – and he gets to wake up next to Iman every morning. In a Soho penthouse. Bastard.