Questlove on Vulnerability: 'I Gotta Be the Change I Want to Be'

More than three decades into his career, Questlove says he still feels like a new artist. "I'm still learning what the Questlove brand is," he told Variety's Jem Aswad at the Variety Experience and Culture Summit: The IRL Advantage, presented by OUTFRONT. "I joke that this is Questlove 3.0 happening right now."

The Roots frontman has spent over a decade in Jimmy Fallon's in-house band, produced the "Hamilton" cast album, teaches as an adjunct professor at NYU, hosts a podcast and has written eight books. Since 2020, he has also directed four documentaries — an endeavor he says he initially resisted most.

"I had to do a lot of work to realize that — I know it's cliché — I gotta be the change I want to be," he said.

What changed his approach to creativity?

Questlove's latest film, "Earth, Wind & Fire (To Be Celestial vs That's the Weight of the World)," was released in June. Directed and produced by Questlove, it traces the band's career and that of its founder, Maurice White. While making it, he read many of the books White read during the band's genesis — reading that he credits with inspiring his current approach to creativity.

The "residue" of that project still lingers, he said, and it has reshaped how he sees himself. Early in his career, he would have named Prince as his North Star.

Why does he keep returning to vulnerability?

Questlove recalled the "too cool for school" attitude he saw in artists like Miles Davis, and recognized in his own records a mindset of protecting vulnerability. He framed the stakes in broad terms.

"We see it in our politics. We see it in our creativity," he said. "We're going to implode as a world if we don't learn what emotions are and how we can use our vulnerability."

His documentaries follow that thread. "Summer of Soul (…or, When the Revolution Could Not Be Televised)," his first, examined the 1969 Harlem Cultural Festival and opened in 2021. "You can't discount the timing of everything," he said of its arrival after lockdown and the protests following the murder of George Floyd. Audiences came out of curiosity, he said, but "they didn't realize how important it was to celebrate joy."

His next film, "Sly Lives! (aka The Burden of Black Genius)," focused on what he saw as a tendency among Black creatives to self-sabotage after success. He made the Earth, Wind & Fire documentary, he said, because he "wanted to make a film that lets us focus on our dreams."

How did he discover he was a storyteller?

Before "Summer of Soul," Questlove did not think he was the right person for the job. "I didn't know I was a storyteller," he said. "I'm out there like, 'Well, search for a real storyteller,' and they're like, 'Dude, you're that storyteller.' Once I realized it, it became a passion."

He described his method bluntly: he uses history to attract audiences, but puts things in his films that make viewers reckon with their present.

What is he doing outside film?

Music remains central. The Roots Picnic held its 18th edition this May, headlined by Jay-Z. The festival has grown, but "we're not just rubber-stamping," he said. "We are curating the festival. We're playing with some of the acts, and people really feel like a community."

On "The Tonight Show Starring Jimmy Fallon," The Roots perform the live walk-up music for guests. Some celebrities send requests for their entrance song, but Questlove holds the line: "the magic of the show is what I choose your walk-on song."

The show's greatest benefit, he said, is that it lets band members be present with their families — and stay together. "The Beatles broke up after seven years, and we're going on year 35 and we're still like the best of friends," he said. "We're still as silly as we were in high school, and still fun. If you're not friends with your partners, then all this is for naught."

With four documentaries behind him since 2020 and the Earth, Wind & Fire project still fresh, Questlove 3.0 suggests the reinvention is only beginning.