“You can leave the lights off,” Ahmir “Questlove” Thompson says. It’s 9:45 a.m. in New York, and the seemingly tireless musical polymath — and cofounder, with Tariq “Black Thought” Trotter, of hip-hop collective The Roots — is in desperate need of a power nap. A whirlwind summer has finally drained his battery.
This summer alone, The Roots hosted the 16th edition of their blockbuster Roots Picnic headlined by Erykah Badu and Jay-Z — in his first major solo performance in seven years, and his only one this year outside of his Yankee Stadium shows; Thompson premiered his critically acclaimed Earth, Wind & Fire documentary; the group returned to the Montreux Jazz Festival more than three decades after its debut there and performed for the opening of the Obama Presidential Center in Chicago — all on top of its 17-years-running gig as Jimmy Fallon’s late-night house band. “I’ll probably look at 2026 as our best bucket-list summer we’ve ever had,” says Thompson, 55.
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For more than three decades, Thompson and his longtime creative partner Trotter have inspired each other to keep the same childlike sense of discovery that took root when they first met as big-dreaming teenagers at the Philadelphia High School for the Creative and Performing Arts. Starting with their 1999 breakthrough, Things Fall Apart, The Roots have released a string of acclaimed albums and picked up three Grammy Awards — and while the group’s lineup has changed over the years, Thompson and Trotter have remained the constants that both anchor it and continually expand its reach.
“The brand is greater than its parts,” adds Trotter, 52. “It’s a beautiful thing, and it’s something you’re only able to achieve over time.”
The Roots have certainly mastered the art of longevity, enjoying a rare degree of creative freedom and commercial success along the way. They have also endured profound loss, including the death in 2014 of the group’s longtime producer and co-manager Richard Nichols. But in the years since, The Roots rediscovered the creative spark that first brought them together. With the guidance of longtime manager and Live Nation Urban president Shawn Gee, Thompson and Trotter tell Billboard they are preparing to release the long-awaited Endgame, The Roots’ first studio album in more than a decade.
With the project nearing completion, Thompson and Trotter say that Endgame is a return to the free-flowing jam sessions that once defined The Roots’ creative process. The group is still chasing the feeling that captivated them as teenagers: pure curiosity.
Thompson (left) and Trotter of The Roots photographed July 15, 2026 in New York. DeSean McClinton-HollandYou guys have been together since 1989. In a genre where even some of the greatest groups eventually break up, what has made the bond between you so strong?
Tariq “Black Thought” Trotter: We’ve been together for such a long time. What else would I consider at this point, right? Long before I met my wife or thought about having children, this relationship, band and dynamic existed. This is something that stood the test of time. There’s no shortcut to that.
Ahmir “Questlove” Thompson: Our first gig, the Montreux Jazz Festival, we were a last-minute addition. This was ’94. For it to come full-circle 32 years later and we did [it] this [past July], I kept saying, “Wow. We’re the same two high school kids who had a janky four-track recorder and a Casio SK-1 trying to figure out how to take two rocks and make fire. And here we are.” We’re still those 15-year-olds maintaining that [love for the music]. Every time I see units and guys saying, “We gotta go solo,” I’m sure it’s the Michael Jordan, Michael Jackson effect of the highlight reel. But we’ve learned that groups and collaborations are probably the wisest way to set a legacy. The solo thing is an illusion because you still need people on the team to do that. That’s what kept us together.
Trotter: We’re still very much fans of the game, and the curiosity is still there. We’ve had so many “We’ve arrived” moments that it’s so hard to count. Everything feels like a new beginning.
How have you guys maintained this level of prestige while never compromising your creative principles?
Trotter: By compromising. (Laughs.)
Thompson: We’ve always trusted the focus group aspect. You can just gauge people’s reactions to things, but also, when you create something, do you get goose bumps hearing it? Does something excite you? And probably the standards have changed. We get better with rejection. I take that less personal now, and it helps me come back with something better. We still care about the product at the end of the day and contrary to popular belief, we still care about success. We’re a business now. We’re still creating and that should count for something.
You guys have expanded The Roots far beyond your music — whether it’s [online community] Okayplayer, The Roots Picnic or your gig with Jimmy Fallon. How have you ensured music stays at the center of everything, even without dropping albums constantly?
Thompson: I’ve learned that we’re in the creativity game and not necessarily the music game. When we [became Fallon’s house band] in 2009, that’s when I observed that all talents are transferable. This doesn’t mean [that] if you’re good at driving an 18-wheeler truck, tomorrow you’ll be able to fly an Air Force pilot jet but just observing and seeing how creators create or being able to spy on Martha Stewart at The Tonight Show and see what kind of sandwiches she’s making or watching comedians punch up a joke empowered us.
When did you realize The Roots had grown into something much bigger than just making records?
Trotter: The last couple of years at The Roots Picnic in Philly. The fact that we’ve been able to expand. We began doing the festival where The Roots would sometimes do two, three sets during the course of the day to keep moving the dial forward. Now we’re at a place where the ecosystem it brings to the city of Philadelphia, the scale it’s grown to, and the fact that there are die-hard Roots Picnic attendees who aren’t necessarily Roots fans — that represents something.
Thompson: I learned that lesson in 2000. The beginning of Okayplayer was The Roots’ website. One day [former group member] Rahzel was on the discussion board and said, “I see this like a playground or a mall, and you guys own a bunch of stores. You can rent out a store to Erykah [Badu], D’Angelo, etc.” Once we ramped up in 2000 and [D’Angelo’s] Voodoo came out, I was a little weirded out. I was like, “Why are people coming in here and they don’t even know this is our coffee table?”
Trotter: Like, how you gon’ diss me on my own s–t? (Laughs.)
Thompson: Right. If there was one regret I had, there was a good hot minute where our site was the destination for almost every journalist to write these stories. It would have been social media. At one point, it became a social system for music minus us. I felt some sort of way about that for at least two years and realized that’s almost the meaning of life. Once you create something and leave it, it can run on its own without your [help].
Trotter: You want your kids to be self-sufficient. This is definitely that way with The Roots Picnic. I think that’s the American dream. Now that I get that’s what real legacy is, then I’m fine with it. The rule is just show up and be ready.
Trotter DeSean McClinton-Holland Thompson DeSean McClinton-HollandDo you think there’s still room for popular hip-hop driven by lyricism and live instrumentation?
Trotter: Absolutely. I think that’s where the most potential lies, right? There’s space for everything to exist. There’s definitely a place where lyricism and true musicianship are going to be more than enough. Is that the consensus or the standard? Not at all. It’s a personal preference. If you’re into lyricism and your musicianship is where it needs to be, that’s just for you and whoever you work with. And then if you invest so much into it that you take it personally when it’s not received as such, yeah, then that’s when people hit these hard bumps in the road and don’t feel like it’s safe to create. I think all that factors in.
Jay-Z chose The Roots Picnic for his first major performance in seven years. How did that moment compare with your Unplugged performance with him on MTV in 2001?
Thompson: This was probably more fun. With Unplugged, we were really just feeling each other out. What [Roots Picnic] taught me was that he’s a regular guy like us. This time around, he was overly enthusiastic about the 30th anniversary [of Reasonable Doubt], which I wasn’t ready for. I thought he was just going to be at a level where he’ll have his folks call me and I’ll put something together. He’s hitting us up at 7 a.m. like, “What we doing?”
There were points where I didn’t seem excited enough, and he was like, “Are you in this?” So I was like, “Let me come up with some ideas and stuff.” But the big takeaway of putting both [performances] together is the importance of legacy and the history of it all. There was a period where I looked at our catalog and thought, “Maybe 30 years from now, somebody will see how much painstaking work we put into this.” It made me want to look at our work with the same reverence because oftentimes when things are in the 20-year cycle, it’s so hard to get people to celebrate themselves. We still struggle with calling this game [an] art form or seeing it as art as opposed to survival.
You’ve worked with Jimmy Fallon for well over a decade now. What has late-night tv taught you about continuing to evolve as musicians?
Trotter: Remaining like water as creatives and performers in the game. The cue-card guys have to be ready for whatever. Cameras 1, 2, 3 have to be ready. A stand-up comic is coming out there, and you may have all your bullet points in front of you and think you have it all figured out, but you have to remain malleable in that performance. The people who stood the test of time are the ones that give a damn about what they do and who consider whatever they do as an art form. If you’re a videographer, that is your art. Being up there every day and getting to interact with the cream of the crop of all these different genres, fields and places they have to offer is contagious.
Thompson: I know it’s a hell of a flex to say, but no Olympic-level athlete or sports champion really gets to that place unless they put time in the gym. Between ’94 and 2008, I would be shocked if you can at least mark us having rehearsal 15 times. No. 1, our shows were mammoth, sometimes two-and-a-half-hours-long. There’s sound checks and constant jam sessions, so we were always in a constant state to play, but we never rehearsed.
Trotter: We kind of pride ourselves in that.
Thompson: That always prepared us to be ready at any given moment, but there is something to be said about going to the woodshed and practicing your craft. So I consider The Tonight Show 11 musicians doing eight to 10 hours a week in the gym because the thing is, our shows have been better than they’ve ever been. And yeah, any job can get monotonous, but we’ve never not played 10 hours a week — minus the pandemic — since 2008. Being in a position where we have to write eight-second themes is a very, very hard thing to do and also just observing how rhythm and timing work, how punch lines and setups land, all that we can apply to where we are now. This is definitely our Beatles in Hamburg, Malcolm Gladwell period.
Trotter: Ten thousand hours be damned. We’re past that.
Trotter (left) and Thompson. DeSean McClinton-HollandThis story appears in the Aug. 22, 2026, issue of Billboard.
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