Questlove, the Coolest Man on Late Night, Is Still Nervous Around Girls

Jimmy Fallon's bandleader cruises around LA, hangs out with Sasha Grey and crushes on Alison Brie

December 7, 2011 11:00 AM ET
Questlove with his record collection
Peter Yang/August

The following is an excerpt of the Questlove feature in the December 26th, 2011 issue of Rolling Stone, on stands December 9th.

Everyone has a favorite Questlove-is-amazing story. Erykah Badu remembers the time he was sick as a dog, drumming at a marathon session past 4 a.m., when he literally nodded off behind the kit. He woke up when he dropped a stick, but still didn't miss a beat. Jay-Z remembers the time they were rehearsing for his Reasonable Doubt concert at Radio City and Questlove (real name: Ahmir Thompson) was learning a new song, counting out the drum parts, and having a conversation all at the same time. ("It was the most amazing thing.")

Jimmy Fallon's might be the best. "Bruce Springsteen came on the show," he says, "and we were going through his old set lists from the Seventies. Bruce goes" – he slips into a perfect Springsteen – " 'Oh, "Wiggle Waggle"! Roots, do you know "Wiggle Waggle"?' And the Roots are like, 'Um, no, we don't know "Wiggle Waggle."' We talk for three more minutes, and as we go to commercial... the Roots start playing 'Wiggle Waggle'! In the time it took to get to the commercial break, Questlove had found it on the Internet, downloaded it and taught it to the rest of the band. Bruce was so excited – it was like Christmas morning. He jumped up: 'Oh, man! "Wiggle Waggle"!'"

With Thompson, even the most unpromising night out has a way of turning into a parade of random cameos. After a DJ set on a recent night in LA, he heads up to Hollywood to meet his friend Sasha Grey, the porn-star-turned-Entourage regular. They met a few years ago when Grey was in a Roots video, and have remained buddies. He meets her outside the Upright Citizens Brigade comedy club, where she just finished judging an improv show. They're standing on the sidewalk being snapped by paparazzi and deciding where to get food when Thompson gets a text from Community star Donald Glover: Did I just drive past you? He says he's on his way to a party and that everyone should come. But Thompson doesn't know if he's up for it; the party is at actress Alison Brie's house, and Thompson has a major crush on her. "That girl is my Kryptonite," he says. "She's gonna have me talking like Back to the Future: 'I'm your density.'" She's been on Fallon before, but he was too nervous to talk to her.

But eventually he's swayed. Up in the Hollywood Hills, Glover answers the door. Danny Pudi, who plays Abed on the show, is also there, along with a few other friends and a Mumford & Sons-ish bluegrass band. Brie takes drink orders, but Thompson demurs; when she disappears into the kitchen, he explains that it's not that he doesn't drink – it's just that his drink taste is kind of embarrassing (e.g., Kahlúa and cream), so he prefers to keep it to himself.

A mini jam session breaks out, with Thompson sitting in on drums and Brie laying down some mean freestyle rhymes. As the night winds down, he gets a few minutes of small talk with her, but in the car on the way home, he's kicking himself. "It's hard, man. As long as my brain is functioning, I'm all types of confident. But there comes a moment where you're just like, 'Oh, shit, oh shit, oh shit...' Now I'm calm and cool and feel like myself again – back to speaking complete sentences. But I had a hard time telling myself to inhale."

He shakes his head. "The last thing I expected to do was wind up in a jamboree singalong trying not to pine over somebody. Strange night."

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