The Last Word: Questlove on Why He Doesn't Drink, Idolizing Dave Chappelle

Roots drummer and 'Tonight Show' bandleader also talks impostor syndrome, Prince's genius, new book on creativity and being a "super-dweeb"

"I still don't know if I am truly creative," writes Ahmir "Questlove" Thompson in the introduction to Creative Quest, his new book exploring what it means to be a creator. "At times I feel like I'm a way better student than I am teacher or maker." Despite winning three Grammys with the Roots and counting author, DJ, designer, producer and culinary businessman among his varied pursuits, music's most affable multihyphenate writes with a deep humility and constant curiosity toward the mindsets of those he admires.

Backstage after a Tonight Show taping, Thompson explains why he wanted to write a book blending his own history of artist collaborations with advice on how to generate ideas, how to deal with failure and how technology has affected the creative process. "I'm asked all the time, 'What advice would you give?' And I hate doing that whole, 'Just stick to your dreams, da-da-da-da-da,'" he tells Rolling Stone, sounding more animated than annoyed. "It's a self-help book for music and art heads."

Part manual, part manifesto, part music-nerd history, part textbook – "I would like this to be a gift that parents give their college students," he says – the book is an indispensable resource for anyone looking to understand the impulse, psychology and spark behind creative ideas.

Who are your heroes?
My dad [doo-wop singer Lee Andrews] taught me everything I know about the music business. But if you're talking about who I look to and worship in my daily life, the Father is Don Cornelius, the Son is Prince and the Holy Ghost is Michael Jackson. The first thing I do every morning is watch an episode of Soul Train. Why? I don't know. Because I can. There's always some Prince surprise around the corner. And the last three interviews on my podcast are heavily Jackson-related.

"I jumped in the river and there's piranhas and sharks, but I have a 500-foot lead on them."

What's the best advice you've ever received?
[Drummer] Bernard Purdie was doing a session for my father in 1975. Dad said, "Bernard, tell my son how you keep food on the table," and he says, "The two and the four." I didn't understand the jargon then, but I know it now. Which is why whenever parents make me meet their four-year-old and the [kid's] looking at me like, "Who the hell are you?" I just say, "You're not going to get this now, but trust me, you'll understand this 20 years from now."

My dad was always a rigorous, bandleading disciplinarian when it came to keeping it in the pocket. That stuck with me. In some ways I've become my dad, especially with the Roots. All of our arguments have to do with numbers. Also, my dad always said, "Son, remember: They can't get you if they can't put anything in you." That's probably the reason I don't drink. I think he had these fears of me partying at a bar and picking up a random person.

What advice would you give to a teenage Questlove?
If the Questlove Jacob Marley figure could go back in time and tell 19-year-old me that you were about to face the hardest 25-year fight of your life, would he still stay in the race? It's like, "I got good news and I got weird news. The good news is you guys are going to be in the industry. You're going to make it. The weird news is that you'll probably be closer to 50 before you get the moment where you can just be like [exhales]."

[Over the years] I had panic attacks over [other people getting] undeserved Rolling Stone covers. I remember, "How the fuck they get five mics [in the Source]?" I threw tantrums; I threw glasses. Many times, I quit. But there was always the hope that one day you were going to make it. I jumped in the river and there's piranhas and sharks, but as far as I'm concerned, I have a 500-foot lead on them.

Was there a career moment, though, when you thought you "made it"?
I knew when I had a DJ gig for the Super Bowl in 2010. I asked my DJ manager, "Wait, how much are they going to pay me for this?" and my manager joked, "Hey, we should make this your new price." I was like, "No!" My thing was always, "Go super under because all I want to do is have something to do after a show." I never wanted to be the guy that just slams on the table like, "Give me six figures," to a club that I knew can't afford that. My manager's like, "Dude, doing these $5 DJ gigs for nine hours is not going to further you along. Trust me on this one."

What first drove you to play hours-long DJ sets?
There's a lot of boredom on the road once you get off the stage at midnight and there's girls and there's Patron there. So I made sure that I was accounted for between the hours of 12:30 and four in the morning. I don't want to start a cocaine habit. DJ'ing was my cocaine.

Why did you want to include a chapter in your book about how to deal with failure?
There have been a lot of pie-in-the-face moments. "Oh, you're Questlove and you're an icon and everyone loves you." But I cry over record reviews and have done horrible projects. It's important to let people know.

I was a little dismayed once Will Smith joined Instagram [laughs]. I have this failure thing on lockdown [claps]. I'm going to be the first person to be like, "Yes, you must fail!" And then Will Smith came with, "Failure is great," and I was like, "Ah, fuck!"

Do you ever get impostor syndrome?
Every day of my life. I was trying to explain to my girlfriend recently: "Look. You know how you look at me as this dweeby nerd that gets on your nerves? You do acknowledge that there are some people on this Earth that hold me in a higher superman regard, but you're stuck with Clark Kent." A lot of us are afraid that we'll get found out as normal. The reason why bodyguards and velvet ropes really exist is mainly because a lot of celebrities don't want you to know how normal and regular they are.

After Things Fall Apart came out and this whole new world opened, there were still questions to answer, like, "Ahmir, why are you still driving that Scion?" I was on a date last year and the girl looked at me like I disrespected her. She's like, "You're driving a Kia Soul? Why?" I was like, "Well, it's boxy, but it's also Afro-friendly and my hair won't be flat when I get out the car. You do know about me, right? You know I do regular guy shit like shopping at Ralph's at three in the morning."

"I cry over record reviews and have done horrible projects. It's important to let people know."

When I interviewed the Revolution, to hear that Prince was doing his laundry and making sandwiches while making "When You Were Mine" in his house. ... He's literally recording a life-changing record and running upstairs [to finish laundry]. I would rather kill all expectations and let you know from the get that I'm a super-dweeb.

What are the most important rules to live by?
Get out of your own head. When I write about that, I'm trying to explain being in the alpha state where you do things so naturally that you don't overthink it. Some people over-prepare stuff and overthink things; some people don't do their homework and just wing it and are under-prepared. But there's that middle place where it's so natural to you that you just don't think about it.

I know I'm coming off like that weird guy that I used to always roll my eyes at whenever I saw people talking about metaphysics and now I've become that person. But my peers overthink shit and call me at four in the morning, like, "I can't!" Panic is just people's default. They don't trust the Force. I'm dismayed that U2's "Get Out of Your Own Way" didn't hit bigger.

You write that your response to seeing someone else's creative innovation is to be "overcome by a kind of paralysis." What was the last thing that made you freeze?
[Dave] Chappelle did a four-hour private show at the Comedy Store at NBA All-Star Weekend. Chappelle is in his mid-1960s free-jazz Coltrane phase. Especially now, when people are finding some of his work problematic. Just to see him have so much confidence ...  He spent 30 minutes talking about pumpkin juice. Thirty minutes! I am thoroughly amazed at anyone who is so confident in the science of their work.

He knows that he is Mel Blanc plus Richard Pryor. He has his whole science thing down from the [impersonates Chappelle] intonation of his voice that reminds you of Mel Blanc and Bugs Bunny. He always does this thing where he'll take a cigarette and not light it and put it to his mouth. He's hypnotizing. He analyzes the science [of comedy] and he'll go out and test it. It's so fearless to me. The best part was, the last three hours? All misses. [Chris] Rock was rolling his eyes like, "Alright, man. Tell Dave, let's go to the restaurant" and I was like "No, man! That's the best part!"

"Bodyguards and velvet ropes exist because a lot of celebrities don't want you to know how normal they are."

Hypothetically, the creators of Black Mirror ask you to create an episode. What's it about?
I'm obsessed with time travel so it's a time travel episode with an African American, but I need them to have two options: They can either travel to an alternate universe in which there's no civil unrest or civil injustice. So if I go back to the 1600s, slavery doesn't exist. However, you're not allowed to take the knowledge that you have with you in present day, so I can't invent the basketball or [know to] make friends with four guys from Liverpool, England, and be their manager. But, if you choose that option, you only get 80 years on Earth and you will have Benjamin Button syndrome and can't get old.

Or, you can take the 10-year test and go back to whatever time period and have to deal with the social consequences, but there's going to be a price to pay. If you can manage to survive those 10 years, you can convince the Beatles that you can be their manager [laughs]. It's the challenge of staying alive.

How far do you think the Roots would've gone if you'd stayed with your original name, Black to the Future?
[Laughs] One and done. One album and that's it. Those [kind of] group names never ...  yeah. But [some crate-digger] would've paid $500 for that one record.

What's the best and worst thing about success?
The best thing about success is I don't know if I have it yet. The worst thing about success is I'm still grasping to get some [laughs].