How much does fear drive your creativity, even at this point of your career?
Questlove: I get afraid when it's over. When we turn in an album, that's when I'm afraid because now you've got to go back down to ground zero. When we finalize a Roots Picnic, like even though Philly is finalized, I'm already dreading next year. Because in my head, it's like, "Fuck man, we're not gonna top this. How are we gonna top what we did last year?" I'm cool with seeing it through at Baltic and Mediterranean properties, but by the time it gets around to Pennsylvania, Boardwalk, and Park Place, when it's near the end, that's when I get scared because I'm like, "You're gonna have to do this again."
If you follow Chris Rock's Instagram stories, he's going through that right now. The Netflix thing is over and he's the type of guy who's very restless. He knows that [Dave] Chappelle is out there. He knows that Kevin Hart is occupying the space. For him to at least remain in the Holy Trinity -- between him, Chappelle, and Hart -- he's gonna have to come relentless. Michael Che is around the corner. There's a few cats that's around the corner, waiting to take one of their spots.
It's very interesting watching Chris. There are four examples of people who I saw creating something pre-November 2016; they started early- to mid-2016, got to November, and the whole Trump narrative forced them to stop and rethink. Of the four, only one of them decided to stick to their guns and stay with what they were going to present. And as a result, this particular person took an ass-whoopin'. In the Trump environment, their particular art was viewed more as tone deaf. Chris was one of the people who had to throw everything away that he'd been working on all summer, pre-November 2016, and start all over again. And at that, he had eight weeks to really come up with something. It forced him to talk about his personal life. Default Chris Rock would have talked about Trump losing the fight to Hillary. The times determine what you put out.
When our manager Rich died, I was scared like a motherfucker. Me and Tariq always sat in the passenger seat; Rich always drove the car and he was the perfect referee. This now means we're gonna have to grow up and be men. It took a few years to get over the funk of not recording one note. Now we're in a space where we can't stop recording. That was another thing Rich was good at: once we got to 100 songs, he'd say, "All right, time to hone it in. Let's pick the best 13." With Tariq, especially after the freestyle shit that he did, he has a whole new lease on life and is writing four new songs a day. We're overloaded and we don't know how to stop. My manager's mad as shit. [Laughs.]