10 Musicians Who Just Keep Getting Cooler As They Get Older

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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.

David Bowie

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.

John Cale

In fairness, John Cale was never uncool – he was always the coolest Velvet, even back in the 1960s – but unlike Maureen “Vote for the Tea Party” Tucker and Lou “Grumpy Old Man” Reed, he’s stayed that way. He’s still performing – if you saw him do Paris, 1919 at Primavera, we hate you – and also still making fascinating, innovative records. And shit, who dyes their hair pink at the age of nearly 70? (We’re also keen for pretty much any excuse to mention his killer cover of LCD Soundsystem’s “All My Friends” – so here it is again.)

Alison Goldfrapp

Like Cale, Alison Goldfrapp was never uncool per se, but when she first emerged onto the scene – providing the vocals for “Pumpkin” on Tricky’s classic debut Maxinquaye, and then releasing her own debut Felt Mountain – she seemed interesting if somewhat anonymous, someone who’d rather let her singing make the statements. That all changed with Black Cherry, when she magically transformed herself into a flamboyant fashionista with a penchant for humping her theremin. Since then, her fashion sense has encompassed everything from a clown suit to a giant peacock feather, all carried off with an inimitable panache.

Peaches

You could never accuse Peaches of shying away from the spotlight – not when the cover of her debut album featured a close-up shot of her pink-hot-panted crotch. But as she’s evolved from potty-mouthed electroclash dominatrix to full-fledged crossover star, she’s used the increased exposure and artistic freedom her status has afforded her to push the envelope in a number of ways – challenging gender perceptions, making crazy film clips, and wearing a coat made of human hair. And, just as importantly, like Goldfrapp she’s also pushing back against the enduring perception that women somehow lose their sex appeal as soon as they enter their mid-40s. And that‘s cool as fuck.

Mike Patton

Back in the 1980s, Flea and Anthony Kiedis apparently hatched a plot to kidnap Patton and shave off his hair so he had to develop his own style instead of aping Kiedis all the time. And we have to say, they had a point – we never liked Faith No More much in the early days, simply because of the fact that Patton came across as a bit of a tool. The days of having Kiedis-esque long hair and pulling silly faces are long gone now, though – these days, Patton’s a dapper gent with a penchant for classy suits and fascinating musical projects. His voice sounds better, too.

REM, generally

It’s strange looking at old photos of REM and seeing how much the band has changed over the years, and particularly the two members named Michael. Sure, Peter Buck was always kinda cool, and Bill Berry never changed much – but look at Michael Stipe and Mike Mills! Stipe has evolved from terminally shy, floppy-haired nerddom into shaven-headed alt-rock godhood. As for Mills, well, the pudding-bowl haircut and wire-rimmed prescription specs have also long since disappeared, although apparently even his own band mates had a collective “WTF” moment when the hitherto reserved bassist suddenly grew his hair and started wearing Nudie Suits circa Monster.

Grace Jones

We remain firmly convinced that Grace Jones remains quite capable of happily breaking us into small pieces if we dared not include her on this list.

Jarvis Cocker

Jarvis’s unrepentant geekishness is, of course, a huge part of his appeal. Pulp endured 15 years of stylish anonymity before they finally hit it big in the mid-’90s with His N Hers, Different Class, and This Is Hardcore, wherein Cocker proved that a lanky man with huge spectacles and a good line in vintage shop suits could be cooler than you could possible imagine. Since then, he’s only grown more stylish with age – and he’s clearly shared his fashion sense with his absurdly cute son Albert, pictured right. (By the way, there are more vintage Jarvis photos here, if you’re interested.)

Mark E. Smith

The Fall’s main man has made a career out of being a curmudgeon who doesn’t give a fuck what anyone thinks – he does his own thing, and doing so is all he cares about, and he’s exactly the same now as he was when The Fall first emerged 30 or so years ago. It seems to us that this is pretty much the definition of cool, so it makes sense that the older and more curmudgeonly he gets, the less of a fuck he gives, and the cooler he gets.

Compay Segundo

A posthumous nomination, but honestly, apart from the grand old man of the Buena Vista Social Club, how many other people have found global stardom and had a legitimate claim for being one of the coolest people on the planet… at the age of 90? We’ll be happy just to get anywhere reaching our ninth decade, let alone look nearly as sprightly as Compay did.