Questlove is stumped.
Sitting in his deluxe apartment in the sky one recent Tuesday night, the Roots drummer is eating an Impossible Burger, no bun, on a bed of roasted cabbage. Something catches his eye midconversation and his chewing slows down. He is visibly flummoxed.
A 1974 episode of "Soul Train" is streaming on the giant flat-screen above his dining nook, complete with vintage commercials for Afro Sheen. Questlove, who wrote a book about "Soul Train," estimates he watches five episodes a day. But now he breaks from polite conversation, distracted by an impossibly funky groove being laid down by a group of 10 impossibly funky-looking dudes.
"I'm curious, do I remember this episode? I should know this song but I don't. It's not Rance Allen..." Questlove trails off. "I thought I knew these episodes like the back of my hand. They finally stumped me."
He rewinds a bit. Don Cornelius announces into his skinny mic that the band we're about to hear is on the Sussex label and they're called the 9th Creation. (Look for "Skin It Back" on YouTube. We can wait.)
"Oh, that's cool as shit!" Questlove exclaims.
Producer, DJ, drummer, professional foodie and amateur comedian, Ahmir "Questlove" Thompson has made a career out of knowing what's cool as shit. His knowledge of pop music—not just the songs, but their historical context; not just the deep cuts, but the engineers on those deep cuts—would make Britannica blanch. But just as he finds himself stumped by "Soul Train" tonight, he comes across over a series of conversations as slightly stumped in general these days. He is, by his own admission, stuck in a little rut. Which is maybe OK because ruts are like grooves. And grooves are his thing.
In interviews at his home and backstage in the "Yacht Rock" dressing room at "The Tonight Show With Jimmy Fallon," where the Roots are the house band, Questlove speaks at length about creativity. His fourth book, "Creative Quest," written with Ben Greenman, comes out April 24 and is an unorthodox exploration of the creative process. Malcolm Gladwell explained how it takes 10,000 hours to master something. But Questlove asks, what exactly do we do in those hours?
The challenge was to provide a peek at his outlook on creativity without delivering a prescriptive one-size-fits-all approach. "If the book teaches multiple people to do things the same way, that's a Pyrrhic victory," says Greenman, Questlove's co-writer on all of his projects. "What's nice about Ahmir's approach is that there are enough entry points—comedy, science, food—and each has a slightly different shape. I hope people will have a certain productive discomfort. Questions aren't answered, but they're asked."
Despite his very public career, Questlove is slightly dreading the speaking engagements that will soon come with his book tour. Ever the sideman, he says he's uncomfortable speaking as "the wise old sage." He'd rather remain a student. But work begets work.
"This is a turning point. This is the most I've said no" to new work, he says. "I'm still knee-deep in work, but trust me, I was forehead-deep in work before."
Questlove is a little tired, you guys.
And no wonder: He is also developing a cartoon for kids with Amazon, based loosely on the story of the Roots, which he describes as " 'Muppet Babies' but all females from South Philly." He is also working on a series for AMC based on Shea Serrano's best-selling "Rap Year Book." He is also (a lot of sentences about Questlove start with "he is also") the host of Pandora's "Questlove Supreme" interview podcast and has projects in the works for both Broadway and the Rock and Roll Hall of Fame, plus one or two other, top-secret off-the-record endeavors. All the while, the Roots are due to release their 18th album this fall. Questlove estimates they have 140 songs in the can. They're struggling to find the perfect 12.
"Forty-five is a hell of a time to start trending," he jokes.
But if that all sounds like a lot, this is actually what it looks like when Questlove scales back. In his new book, he tells a story about a "hush-hush" party he was hired to deejay last year. It was meant to be a triumphant set. His best gigs are awe-inspiring and educational, omnivorous and funky, eclectically hip but also booty-rockin'. "He moves through time and space in pop culture and music like nobody else," says Evan Pollock, the creative lead on "Questlove Supreme." "He shepherds you through that narrative."
But the 2017 party was a bust. They wanted the current hits. The host made him redirect his set to play crowd-pleasers. And the crowd was pleased. But Questlove felt deflated.
"That took a lot of air out of my sails. I spent three months not really deejaying," he says today. "Everyone will say I'm being melodramatic. I think my feelings are valid."
Last summer, he took up Hollywood macher Shep Gordon's invitation to visit him in Hawaii to unplug a bit. For the first time in decades, Questlove did nothing for four solid days. Well, not nothing: He rewatched most of "Friends." (He points out that Lin-Manuel Miranda famously read "Hamilton" on the beach—and then wrote a certain play about it. Questlove, who co-produced the "Hamilton" soundtrack, jokes that maybe he'll do a "Friends" hip-hop musical.) What he does know is that he didn't like being so idle.
"I definitely rebooted, but it scared the shit out of me. That was my fear: If you ask me to stop, I might stop forever. I couldn't believe I let four days go by. I guess you fight what's good for you," he says. Still, it sparked something in him (or maybe it muffled something): For the first time in his career, he says, "I see an exit plan."
Every year around this time, Questlove typically cleans house and creates a whole new DJ set to last the year. He likens it to when a comedian, like his friend Chris Rock, has to toss out old material once it gets too familiar. Rock just released a Netflix special, so now he has to go back to square one.
"This is my favorite Chris Rock. He doesn't know what to do," says Questlove. Rock spends his days tooling around his New Jersey neighborhood, going to the mall, calling Questlove to ask what he should stream next. "He has to start from scratch. I'm at that point as well." Only, he can't seem to get unstumped.
"I'm doing the math. In 2019, basically 1998'ers are 21," says Questlove. "I just start dreading. Wow, another generation that won't know 'Don't Stop 'Til You Get Enough,' that won't know what a Wu-Tang Clan is. My whole thing is including the history of music. But now as time goes on, I'm going to have to move the bracket up more." Even Pharrell is old-school now, he says, except maybe "Happy." And so, increasingly Questlove is creating parties for families with his "Breaks for Kids" series. It's an opportunity to introduce a new generation to classic jams while they're still impressionable.
Questlove's creative driver has always been about nostalgia in some sense. He was born during a wave of nostalgia: His father was Arthur Lee Andrews Thompson, who enjoyed some fame as the frontman of Lee Andrews and the Hearts, a '50s doo-wop group. Young Ahmir would make his onstage debut at Radio City Music Hall 30 years later at 12, playing drums for his family band's oldies revue.
Growing up in a middle-class musical family in West Philadelphia in the 1980s instilled in Questlove a determination to never land on his own oldies circuit. "Sometimes, there would be six gigs a month. Sometimes one gig," he says. "Their whole thing was like, 'We're keeping you in private school so you can make it in life and not scrounge like we're doing.' But that period, like '84-'87, maybe the gas was on, maybe it wasn't. Maybe the electricity was on, maybe it wasn't. No water? Go to grandma's house. That instilled a never-again chip in me, which made me relentless."
Questlove attended the Philadelphia High School for the Creative and Performing Arts at an especially fertile moment. His classmates included jazz bassist Christian McBride, guitarist Kurt Rosenwinkel, jazz organist Joey DeFrancesco, singer Amel Larrieux and the members of Boyz II Men.
"We were all a little weird," says Questlove's classmate Fern Glazer (née Sternberg), a writer. "But there were people—like Joey, like Boyz II Men, like Ahmir—you just knew they were bigger than that place." Another thing that stood out was his relationship with Tariq Trotter, who, as Black Thought, co-founded the band with Questlove that would become the Roots.
The two have been collaborating for 30 years now, through 17 albums and as Jimmy Fallon's house band since 2009. The Roots are an anomaly in hip-hop: a full band of instrumentalists, informed by the soul of the '70s, unapologetically political and prolific, relentless road dogs for their first two decades, high-profile underground kids with just a kiss of ultra-mainstream success. (In Questlove's guest bathroom, there is a broken Grammy perched atop the toilet, awarded to the Roots and Erykah Badu for Best Rap Performance by a Duo or Group in 2000.)
Signing on as the house band for Fallon's "Late Night" and then "The Tonight Show" bought some lasting security for a no-longer 20-something Questlove. "Once we got our first mediocre review for 'The Tipping Point' [in 2004], that sparked an 'Oh shit, I could lose this; I could be on the oldies circuit' feeling," he says. It took a few years before "The Tonight Show" came calling, and at first, "I didn't necessarily see it as an answer. I saw 'The Tonight Show' as a very quiet way for us to die. Keep the bills paid, keep the families and the kids close to us. I never thought it would be a new lease on life." (Unlike several of his bandmates, Questlove is unmarried and has no kids, though he has a serious girlfriend.)
Working with Fallon has exposed him to new artists he wouldn't have otherwise worked with. "If I weren't at 'The Tonight Show,' I would probably be the old guy complaining. Which is natural," he says. "I love Rich the Kid. Tyler [the Creator] is one of my favorite people ever. He made his debut on this show. There's a slew of acts—Little Dragon, Dirty Projectors—had it not been for the show, I would probably have not known."
And it's allowed him to try new things. For years, Questlove had put all of his eggs in one basket: music. The Roots. His side projects with artists like D'Angelo, Badu, Common, Fiona Apple, John Mayer and others. But increasingly, he was looking to other outlets. He found one in comedy, another in food.
By 2012, he was co-hosting a stand-up comedy show and curating "Shuffle Culture" events at the Brooklyn Academy of Music. (Shuffling is a dominant metaphor for Questlove. Put your whole music collection on random. See what happens. Put your friends on random. Put your food on random.) He launched a catering service called Quest Loves Food that morphed into food salons he hosted at his penthouse. He'd invite top chefs from around the world and hold court in his apartment with them and guests like Björk and Padma Lakshmi. Those salons became the foundation for Questlove's third book, "Something to Food About," in which he interviews chefs about their own creative processes.
"He came to our restaurant religiously on the first day of a new menu," says Daniel Humm, chef and co-owner of Eleven Madison Park, recipient of three Michelin stars and once ranked best restaurant in the world.
Questlove has deejayed at Humm's parties, including the night Eleven Madison Park closed last June for a four-month renovation.
One Humm party in particular Questlove characterizes as "Eagles-, Zeppelin-level debauchery. And I've seen some shit. I never thought in my life the most debaucherous shit I've ever seen would be at Eleven Madison. But once you buy 500 bottles of 1987 champagne, all bets are off. It turns into Sodom and Gomorrah." Questlove, who is not a big drinker, says he bounced when too many liquid refreshments had been spilled on his gear.
Still, the excursion beyond music is worth it. "A meal at Eleven Madison was the equivalent of, for three hours you got to own a Rembrandt, and once it's done, there's no evidence of it," he says.
Questlove still squirms at the mantle of leader, driver of culture or, for that matter, brand in his own right. "Am I a teacher or a student?" he asks, a common refrain of his. "I've always been in the passenger seat of pretty much everyone's creative journey. Jimmy takes the weight, Tariq takes the weight, D'Angelo takes the weight. I'm in the passenger seat."
It's a cop-out, of course. The curator gets to hide behind the playlist of other people's work. Todd Haynes' biopic of Bob Dylan, "I'm Not There," resonates with Questlove, who wanted the audiobook for his memoir "Mo' Meta Blues" to be done in a similar vein, with multiple actors playing him at different stages in his life. He's not there. He doesn't have to take the weight.
But the weight has a way of finding you when you're on TV every night. "I'm not naïve to the point I don't realize that there are cool-hunters out there who are looking for the stamp of approval. Why I'm the level of cool or why my opinion matters to people is baffling," he says.
He's passed on myriad sponsorship opportunities that didn't fit. He recently turned down a national fast-food chain that approached him after a taco-related tweet (he tweets a lot; his Instagram feed is a delight). To his chagrin, his managers made him reject a walk-on role on "Sharknado 4" (he loves Shark Week). Sometimes, it works out, though. The band recorded an anthem for the 2015 NBA Finals and revamped Dee-Lite's "Groove Is in the Heart" for Target, for example.
"We model a lot of his business activity around things that he's passionate about," says 20-year Roots manager Shawn Gee. "Even the business of deejaying didn't start with a business plan or an idea to build out this entity and make money. It wasn't driven by commerce. He started at the beginning of his career with the Roots, and for several years, he didn't get paid for deejaying; it was an act of passion. We collectively built a business around it."
Stella Artois came to the band with a pitch that made sense to them. In 2016, the Anheuser-Busch InBev brewer approached the Roots ahead of its "Host One to Remember" campaign. The group was tasked with creating two versions of one song, called "Bittersweet"—one tune bitter and the other sweet—and then performing them at a dinner party.
"So in my mind, one is complete minor, the other is in the relative major," says Questlove. "There is a big giant creative component of creating and curating a song at a dinner party that really interested the shit out of me. Plus, it took us out of our comfort zone."
The fact is, even afraid of the comfort zone, even slowing down, Questlove is pretty comfortable.
"My comfort zone is half artist, half suit. It works for me," he says. "I'm a suit in the way that Billy thinks that Kevin is a suit on 'Entourage': 'suit' being a four-letter word. I'm totally that."
At a recent "Tonight Show" rehearsal with Tracy Morgan, as the comedian went off on wild tangents, the job of reining him in fell to Questlove.
"He's ranting one-liners. 'Everyone's my biological father!' And, 'Get her pregnant!' " says Questlove in a spot-on Morgan impression. "At some point after the 12-minute mark, I'm like, 'Can we start the song now?' He's all, 'Come on, Quest. What, you a suit now?' Sometimes I do catch contemporaries staring at me like, 'Did you change?' There is no selling out. There is such a thing as responsibilities. My days of 4 a.m. sessions are over."
Just before dinner that Tuesday night, he certainly doesn't seem like a suit, though. His big shambly body, in jeans and an oversize blue button-down, is slouching over a box of records in his home office. His famous Afro is braided tightly and neatly to his scalp in cornrows.
He's digging through stacks of vinyl that his record buyer recently sent to him. Just a kid and his record collection. He puts on one long-sought-after rarity that he recently found. It contains a cheesy cover of the Beatles' "Hard Day's Night" that his friend the late producer J Dilla sampled. (Out of respect for the DJ code, we've sworn not to reveal the source. But we did cop our own copy off Discogs.)
Questlove drops the needle and surprises even himself: yet another song Dilla sampled (a cheesy cover of a Simon and Garfunkel tune). His eyes, the right one slightly lazy, get wide behind his glasses.
"Fuck, I'm so mad right now. How did I miss this?!" he says. He snaps a quick video that he sends to a friend in Portland, Oregon. "My girl asked like, 'Yo, how much did you pay for that?' Dude, it's gold. She's like, 'I don't get it.' I mean, I know it's not the stuff hip-hop dreams are made of."
But creativity can be found anywhere. "The thing with Dilla," he says, "is that he taught us that, more than anything, you don't have to find the obvious record that has the obvious drum break in it."