More than three decades into a multifaceted career, Questlove remains eager to evolve. The Roots frontman, who has served as the bandleader for Jimmy Fallon’s late-night show for over ten years, has expanded his creative footprint to include producing the “Hamilton” cast album, teaching as an adjunct professor at NYU, publishing eight books, and hosting a podcast.
Since 2020, he has also helmed four documentaries, a path he initially resisted. Speaking with Variety’s Jem Aswad at the Variety Experience and Culture Summit: The IRL Advantage, Questlove admitted he had to overcome his hesitation. “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.
Now referred to by the artist as “Questlove 3.0,” this new chapter was catalyzed by his work on “Earth, Wind & Fire (To Be Celestial vs That’s the Weight of the World),” released in June. The documentary explores the band’s history and that of founder Maurice White. In preparing for the project, Questlove read many of the books White consumed during the band’s early days, which reshaped his own creative philosophy.
He reflected on the “too cool for school” personas adopted by artists like Miles Davis, noting that such attitudes often serve as a defense mechanism to protect vulnerability. Warned of the dangers of emotional suppression, Questlove stated, “We’re going to implode as a world if we don’t learn what emotions are and how we can use our vulnerability.”
His documentary journey began with the 2021 release of “Summer of Soul (…or, When the Revolution Could Not Be Televised),” which chronicled the 1969 Harlem Cultural Festival. Questlove acknowledged the significance of the film’s timing, arriving after the George Floyd protests and pandemic lockdowns. He observed that audiences were drawn to the film out of curiosity but ultimately needed its message celebrating joy.
His subsequent projects continued this exploration, with “Sly Lives! (aka The Burden of Black Genius)” examining the tendency among Black creatives to self-sabotage after achieving success. Questlove emphasized that he did not originally identify as a filmmaker. “I didn’t know I was a storyteller,” he recalled, noting that others encouraged him to take the role. He now views his approach as using history to draw audiences in while embedding content that forces them to confront their present reality.
Despite his focus on film, Questlove has maintained his musical commitments. The Roots Picnic celebrated its 18th anniversary in May with Jay-Z headlining. He stressed that the festival is carefully curated rather than simply repeated, fostering a strong sense of community.
On “The Tonight Show Starring Jimmy Fallon,” Questlove retains control over the band’s performance, particularly the walk-on music for guests. He noted that the best aspect of the long-running show is the time it allows band members to spend with their families. Highlighting the group’s longevity, he said, “The Beatles broke up after seven years, and we’re going on year 35 and we’re still like the best of friends.”
His point about vulnerability is spot on, but I still miss the early Roots jam sessions.
‘Questlove 3.0’ sounds like a superhero suit upgrade. Did he mention his favorite Earth, Wind & Fire track?
I never realized how much Questlove produces. That documentary work is seriously transformative.