Questlove Reflects on the Power of Vulnerability and Being a Trailblazer: ‘I Gotta Be the Change I Want to Be’

More than 30 years into his career, Questlove is still open to change.

The Roots frontman and multi-hyphenate has performed in Jimmy Fallon’s in-house band for over a decade, was a producer on the “Hamilton” cast album, is an adjunct professor at NYU, hosts a podcast and has written eight books.

Since 2020, Questlove has also directed four documentaries. It was that endeavor that he was initially most opposed to: “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.”

Questlove sat down with Variety‘s Jem Aswad to discuss embracing vulnerability and being a changemaker at the Variety Experience and Culture Summit: The IRL Advantage presented by OUTFRONT.

Questlove said he would have called Prince his North Star when he first entered the industry. Now, with the “residue” of his Earth, Wind & Fire documentary still lingering, he said he feels like a new artist. “I’m still learning what the Questlove brand is,” he said. “I joke that this is Questlove 3.0 happening right now.”

“Earth, Wind & Fire (To Be Celestial vs That’s the Weight of the World)” was released in June. Directed and produced by Questlove, the documentary explores the band’s career and that of its founder, Maurice White. While creating the documentary, he read many of the books White read during the band’s genesis, which inspired his current approach to creativity.

Questlove recalled the “too cool for school” attitude he saw in artists like Miles Davis and his own mindset on his records as protecting vulnerability. “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.”

Questlove’s first documentary project, “Summer of Soul (…or, When the Revolution Could Not Be Televised),” about the 1969 Harlem Cultural Festival, came out in 2021. “You can’t discount the timing of everything,” he said of the film’s arrival after the initial lockdown and protests following the murder of George Floyd. He said people saw the film because they were curious, but “they didn’t realize how important it was to celebrate joy.”

His next project, “Sly Lives! (aka The Burden of Black Genius),” focused more on the tendency he noticed in Black creatives to self-sabotage after becoming successful. Then came the Earth, Wind & Fire documentary, which he made because he “wanted to make a film that lets us focus on our dreams.”

Still, Questlove didn’t think he was the right person for the job of documentarian prior to “Summer of Soul.” “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 himself as someone who will use history to attract audiences, but will put things in his films to make the audience reckon with their present.

While he has ventured into filmmaking, Questlove has not left music behind. The Roots Picnic held its 18th iteration 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 serve as — among other things — the live walk-up music for guests. Some celebrities send requests for their entrance song, but Questlove said, “the magic of the show is what I choose your walk-on song.”

The best thing about “The Tonight Show,” Questlove said, is that it allows the band members to be present with their families. “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.”