Depending on who you ask, Questlove is either Jimmy Fallon’s bow-tied sidekick, or the drummer and cofounder of the legendary hip-hop ensemble the Roots, or a producer of hits like the Hamilton cast album, or the host of a weekly Pandora radio show, or a music professor at New York University, or simply one of those one-word names—like Cher or Drake or Moby—who show up in your pop-culture consciousness one day and never leave. To the man spinning in his swivel chair backstage at 30 Rock, it doesn’t matter much.
“Being underestimated has always been my calling card,” says the 47-year-old maestro, gesturing to a live feed of Fallon rehearsing in the Tonight Show studio. “When I first got here, someone said it was like seeing Miles Davis busk in the subway.” He was glad for the insult. “I go into things hoping you underestimate me,” he says. “If people have lower expectations, that’s the best way to experience my projects.” He once got into an argument with a record executive and said, “You’re not going to miss us. You don’t even know my real name.” The exec replied: “OK. You got me there.”
Questlove, for the record, is really Ahmir Thompson, born in Philadelphia but raised on the road by parents who were traveling musicians. At age 13, after perfecting his skills playing buckets on the street and becoming a musical director, he enrolled at Philly’s High School for the Creative and Performing Arts (Boyz II Men were in his year). He and classmate Tariq Trotter founded the Roots before they even graduated—and went on to collaborate with almost every heavy hitter in the music industry—earning near universal respect and 14 Grammy nominations.
Beneath all the success—and the most recognizable afro on the planet—is a creative drive that extends far beyond his own music, fueled by idiosyncrasies and obsessions, including what he describes as a shamefully deep knowledge of Soul Train trivia, an unlikely love of Crazy Ex-Girlfriend, and an insistence on seeing a play three or four times before trying to understand it. Questlove is a creator who identifies as a musician, but as a rule he likes to surround himself with artists of different disciplines—and prefers never to be the smartest person in the room.
With New Yorker writer Ben Greenman, he’s put all that he’s learned about inspiration into a new book—his fourth—called Creative Quest, out in April, which is packed with patient, deliberate breadcrumbs intended to help people get unstuck creatively. Drawing from his own experience with artistic frustration, he writes passionately about the benefits of travel and what he calls being “actively away.” Creativity, he says, is “not about taking breaks or pauses or naps. It’s about excursions. It’s about departures.”
It’s an approach he discovered on his first-ever vacation, shortly after joining Fallon in 2010. “I was a hobo for four days from New York to San Francisco,” he says, recounting a train trip that took him from New York to Pittsburgh, through Chicago and Salt Lake City, and on to the West Coast. “Just the best trip of my life. Looking out the window and getting lost.” For him, it wasn’t about getting to San Francisco—it was about arriving there as a new man. “Do you know that 90 percent of my dreams are train-based?” he laughs. “I’ve been stuck in the same dream for the last 20 years. Sometimes I do the train travel thing to find completion.”
Appropriately enough for a man who calls himself Questlove, he also knows he’ll never get all the answers. “If a question comes into perfect focus,” he says, “answering it isn’t creative anymore.”