1. Questlove was a sputtering, nervous mess when he first met his idol, Prince.
Q-Tip introduced Quest to Prince at a nightclub in downtown NYC, but the drummer was more than a bit stunned when he realized his idol knew who he was:
Words, finally, appeared in the gurgling. “Yeah,” I said. “Just that…you are…knowing who I…be.”
Q-Tip translated. “He’s amazed that you know he’s alive.”
“Right,” I said. “That you be knowing me. That, I, I mean you, I mean. You know. That the thing is.” At this point, Q-Tip shot me a glance. It was the look you give a guy in a plane when it’s going down. Time to hit the silk. “I’m going to go,” I said, and I went.
2. After his parents threw away (and even broke!) his records from artists they thought were inappropriate — Prince, The Time, Vanity 6 — Questlove recorded them onto cassettes and hid them inside his drums.
3. Hearing D’Angelo for the first time changed Questlove’s life.
He was frustrated with what R&B had turned into, lacking “authentic passion” and “soulless.” But then he heard D’Angelo’s Brown Sugar:
It changed my life. Here was a singer who connected with me as deeply as the best hip-hop. It was the first album, of course, the sensibility that powered the songs, the ability to locate the heart of the best soul music. It was out of step with the times but in a way that made it seem like he was stepping into uncharted territory.
But he had actually passed up the chance to work with him! After being offered to play on the song “Shit, Damn, Motherfucker,” Quest passed, having sized up D’Angelo previously when he’d come by the studio, thinking “eh, another corny R&B guy.”
“I had no clue that he was going to be the second coming,” he writes.
4. The Roots’ residency on Jimmy Fallon is the direct result of a human pyramid.
The drummer had initially been set on declining Jimmy Fallon’s invitation to have The Roots become his house band. But after he invited Fallon to one of their shows, that all changed. Fallon had been hanging backstage, and after just ten minutes, Questlove came back from an interview and saw something he never thought he’d see: Jimmy “with almost the whole band — Tariq, Tuba, Owen, Frank, Kamal, and others — making a huge human pyramid.”
The group was laughing; in general, the band had been enjoying themselves and having more fun those days. “Jimmy brought all of that to a boil, in the best sense,” Questlove writes, “and I couldn’t help but laugh at how silly they all looked. Oh, shit, I thought to myself. We’re stuck with this guy, aren’t we?”
5. Kanye West’s performance of “Jesus Walks” for Dave Chappelle’s Block Party was the moment Questlove felt a changing of the guard.
We were shooting a performance of “Jesus Walks,” and Kanye wanted to come in with a marching band. I remember a welter of political and artistic thoughts crowding my mind. I thought about how presidential he looked and how the black kids were responding to him, something I had ever really focused on in our own audience. I remember having a kind of out-of-body experience and investigation of the thought of my own artistic death. “Am I dead already?” I wondered. […]
I remember […] thinking to myself, “Oh, I see. This is where I get off.” I saw the rest of the plot stretched out before me. Kanye was going to be the new leader, and I was fine with that.
6. According to Quest, the single most influential moment in the history of hip-hop was the Stevie Wonder episode of the Cosby Show.
“Why do I say that this episode changed hip-hop forever?” Questlove asks. “Simple: it was the first time that 99 percent of us who went on to be hip-hop producers saw what a sampler was.”
He marks that as the moment he got sucked into hip-hop production; it was the first time he’d seen a sampler, just as it was the first time for so many other legendary producers, like J Dilla and Just Blaze. But they weren’t sure of exactly what it was.
At that point, it was just something cool on a sitcom, and in response to it, in awe of it, an entire generation of talented, ambitious black kids leaned forward in their chairs to the point of falling out.
7. He was initially hesitant to work with Jay-Z because he felt he was the “antichrist to a certain kind of hip-hop fan.”
When The Roots were offered the chance to be Jay-Z’s backing band for his MTV Unplugged performance, Questlove admits that he was initially skeptical, even though he was a fan: “Admiring him was one thing — but collaborating with him? That seemed like it could be a real train-wreck of cultural signifiers: his big-money, above-the-title hip-hop, our legit indie reputation.”
But after working together on Unplugged, he discovered that Jay turned out to be one of the “easiest people to work with” that he’s ever encountered. They were two music nerd peas in a pod.
8. The Roots began, as most bands do, in part to impress a girl.
Amel Larrieux was the “beautiful, kind” girl in high school (who later became a star herself, in a group called Groove Theory), and 18-year-old Questlove wanted to impress her. So, naturally, he told her he was performing with his then-acquaintance, Tariq, at the talent show, even though they had nothing planned. Luckily, they gathered up a band made up jazz kids and experimentalists, and that marked the pair’s first live performance, where Ahmir “Questlove” Thompson and Tariq “Black Thought” Trotter performed as Radio Activity.
And he later took Amel to the prom. Awww!