Questlove Embraces Financial Freedom No More ‘Taking Every Job’

It’s easy to think that Questlove has never been busier than he is right now. Between getting ready for his Roots Picnic music festival in June, his day job at The Tonight Show (where his band the Roots is the house band), running his publishing company AUWA (his first book for kids, The Rhythm of Time, will be released on April 18 by Putnam, an imprint of Penguin Young Readers), and his many movie projects, he has a lot going on. But the artist with many skills now has less to do.

He thinks that between 2015 and 2017, he had about 19 different jobs, one of which was teaching music at New York University. “It gave the press a lot to talk about,” he laughs to PEOPLE. But with girls you like? In no way.

“They would say, ‘If you take this job at NYU, we won’t be able to be together,'” he remembers. “As a child, I lived in fight-or-flight mode, living from week to week, check to check. I thought I had to take every job that came my way.” Questlove didn’t start to see things in a new way until the pandemic. “The universe told me to stop and listen to what my heart was telling me.”

“You go for what makes you excited,” he says of his present view. During the lockdown, he wrote The Rhythm of Time and finished Summer of Soul, a movie about the 1969 Harlem Cultural Festival, which he calls a celebration of “Black joy.”

In 2022, the film won the Oscar for Best Documentary, which he says took him from “hiding in plain sight” to a new level of fame. “Playing the shy, humble Clark Kent role doesn’t help anyone,” he says. “When I saw how happy Summer of Soul made people, I knew I had to do something.” “I have to be the change that I want to see.”

Questlove Embraces Financial Freedom No More 'Taking Every Job'
Questlove Embraces Financial Freedom No More ‘Taking Every Job’

Questlove ‘Taking Every Job’

“[Questlove] has become more than just a musician,” says John Mayer, who has known him for a long time and worked with him. He is a historian and a teacher for young people.” Ahmir Thompson is the son of singers Arthur Lee Andrews and Jacquelin Thompson.

While on tour with his parents, he got his first taste of the stage. “They didn’t believe in babysitters—they weren’t popular until the 1980s,” he says. “I had to go to work with them when they played in bars from 8 pm to 2 am. Also, they wanted to keep an eye on me, so they made me play the shaker and cowbell on stage when I was 6 years old.

After the drummer broke his arm in a motorbike accident when he was 12, he got to play at Radio City Music Hall with his dad’s band. He says, “They took me to Macy’s and bought me a suit jacket. I was my dad’s bandleader and played the drums for the show.”

“All he had to do to make me happy was give me $150 and some records.” After high school, Questlove and his friend Tariq Trotter, who is now known as Black Thought, formed the Roots. Organix, their first record, came out in 1993, but it wasn’t until “You Got Me,” which they made with Erykah Badu, that they became well-known in the mainstream.

In 2009, they got a job on Late Night With Jimmy Fallon, which gave them security and a bigger audience. “That was our first real break,” says Questlove. Since then, the Roots, which has had more than 20 different players over the years, have been with Fallon, even when he moved from Late Night to The Tonight Show in 2014.

“From high school until a month before Late Night, we spent 250 days of the year on the road,” says Questlove. “We were together too much, and two tour buses were my manager’s only solution at the time.” We used to make jokes about the tour bus for Gryffindor and Slytherin.

That’s how we lived, and even though we only saw each other during shows, it kept the group calm. Fallon gave us the chance to grow up for the first time in our lives. He jokes that the band all went to therapy together, which he says is “a real thing, not just for Metallica.”

“As Tariq and I grew up, the shows got more fun to watch.” When the pandemic stopped production of The Tonight Show in the studio, Carson worked from a friend’s farm in upstate New York, where he found a new spark of creativity. He says, “It was my chance to be 8 years old again.”

“I got to dream, make up stories, and play without worrying about whether or not I would make it.” He was moved to start writing The Rhythm of Time, a story about a seventh-grader who loves rap music and finds himself in Philadelphia in the 1990s.

“I’d always wanted to write the book I wished I’d had when I was a kid: a time-travel story about a music geek.” He says, “But I never took it seriously because I didn’t know enough scientific jargon.” Summer of Soul had a hard time getting used to all the attention when he started to win awards at festivals last year.

“I would think, ‘Oh man, everyone hates me now,'” Questlove says. “At first, they were excited, but now they just say, “He’s here, you know he’s going to take it.” “I started to think, ‘This is why I don’t deserve this.'” Then, at the Oscars, he did something unexpectedly weird: he won right after Will Smith slapped Chris Rock onstage.

He says, “I didn’t even know what was going on until maybe 90 seconds in.” “When you’re up for an award, you’re not in your right mind.” It took me about two months to understand everything that had happened.” Questlove used to keep his awards (he also has six Grammys) in his bathroom, which he called a “performative humble act.”

But now he has a different point of view: “I had to look myself in the eye and tell myself, ‘You won this Oscar.’What do you want to do with the rest of your life? “Are you going to hide or are you going to step up to the challenge?”

Questlove wants every project he works on today to have a “teachable lesson,” whether it’s about addiction in his upcoming documentary about singer Sly Stone or about class differences in a planned live-action version of Disney’s Aristocats.

The singer says he wants to take a real break, which may even surprise him. But, as he points out, that day isn’t likely to come until 2027, after these two movies and four others are done. “Then I’ll be satisfied,” he says. “I definitely want to slow down and enjoy life, find love, start a family, and all that, but I’ve come too far to drop the ball now.”