In an industry of conformity, Questlove remains a hip-hop iconoclast

“I'm in the lion's den,” Questlove blurts out before I can ask the first question, with a laugh that confirms he’s being eaten alive online.

Our interview, arranged one month prior, is supposed to be part of a routine promo run for the release of The Roots drummer and bandleader’s new book, Hip-Hop is History. But when our scheduled time to talk rolls around, it happens to fall in the same week that his thoughts on the present state of rap have generated some unintentional press. In a late-night Instagram screed, he’d responded to the Kendrick Lamar vs. Drake battle, and all the hype surrounding it, by declaring, “Hip-hop is truly dead.”

It was either the perfect pitch for a book that chronicles rap’s recorded history through Questlove’s hyper-subjective lens, or a publicity nightmare. Whatever the case, it generated plenty of predictable discourse: “What the Hell is Wrong With Questlove These Days?” read one headline. Hyperbole or not, Questlove’s IG post garnered such a hot response for the same reason that reading his book — or having a conversation with him — is so compelling. In an industry of conformity, he remains a hip-hop iconoclast, and a self-professed “dweeb,” who’s never been afraid to drum to his own beat. “You're probably the only person that's going to get the official word,” he tells me, explaining why this will be his first and only deep dive on what was so triggering about the biggest hip-hop beef of the 21st century. “I'm not trying to do a mea culpa post-tour of explaining myself.”

The concern that emanates from Questlove goes deeper than rap. It’s rooted in a reverence for Black life and Black genius, and the understanding that both get compromised beyond recognition on the regular. That fact animates his life’s work as a multihyphenate with so many seemingly disparate side hustles, the latest of which includes a forthcoming documentary on Sly Stone to complement the memoir Thank You (Falettinme Be Mice Elf Agin), published on Questlove’s own imprint, AUWA, last year.

In this sprawling interview, we talk about what made him lose (and regain) his passion for hip-hop, why he and Black Thought are finally returning with a new album from The Roots after a decade, and how self-sabotage is an unfortunate byproduct of Black success — even for a book-publishing, documentary-directing, hip-hop ambassador with an Oscar to his credit. I started by asking him about the Hip-Hop 50 tribute he curated in 2023, which caused him so much stress he lost a tooth.

This interview has been condensed and edited for clarity.

Rodney Carmichael: In the intro of your new book, Hip-Hop is History, you talk about putting together the Grammys’ tribute for the 50th anniversary of hip-hop last year, and how you had to become, like, a master negotiator to get these legendary artists to say yes.

Questlove: Well, how I wound up on an operating table. Yes.

With so much bad blood between rap and the Grammys, what convinced you to put yourself in the line of fire like that, knowing that there would be criticism no matter how it went?

I saw this as a seat at the table moment. Here's the thing: For us to walk through life — and by us, I mean Black people — it's a constant journey of living in fight or flight. There's never a period where you actually feel safe, or I can drop my guard for half a second. That said, you often have choices to make. And for a lot of us, especially in Generation X, you kind of walk through things knowing that you're going to have to be part of the long-game journey.

Everything that I'm doing in this life, I'm doing knowing my mission. I know it sounds lofty, and some could say it's a naive outlook, but I generally would like to leave the world better than when I came in it. And not in this 1980s, “We Are the World,” let me heal the entire world [way]. I believe if I can really affect 500 people, maybe 5,000 people, even 50,000 people, then at least I planted a seed.

I realized, maybe 10 years ago, that my 40s were creeping up on me — that one day, I'm going to be the adult in the room. And there's really nothing glamorous about that path. There's nothing sexy about it.

Especially not in hip-hop.

And just in general. In the last 15 years, I've been the guy that's always on the sideline like, “Who's going to be the person to make the change?” And the universe always points to me like, You're going to have to be that person. Of course, I could start making self-evident reasons for why I shouldn't be that person — I'm no stranger to imposter syndrome or self-sabotage; I'm more aware of it now than I was — but I was, like, You're not famous enough to be that leader, or, You don't have enough hits under your belt. So, long story short, if not me, then who?

When things hit a crescendo in the Kendrick versus Drake battle, you wrote what kind of felt like an obit for hip-hop in response. Are you in a place where you can read that Instagram post?

Sure. I said, “Nobody won the war. This wasn't about skill. This was a wrestling match level, mudslinging and takedown by any means necessary — women and children and actual facts be damned. Same audience wanting blood will soon put up R.I.P. posts like they weren't part of the problem. Hip-hop is truly dead.”

When did you realize that what you said maybe was not quite being received in the way that you intended?

All right, here's the deal. I wish people would make up their minds. I'm in this weird middle place — and I talk about this a lot in my books. I live in the zone where I'm somewhere in between “Dude, you changed my life!” and “You ain't s***!” Every day. So it's a constant balance, and you don't know what the reaction is going to be.

As you outline in the book, one of the foundations of hip-hop is competition. We’ve had some classic battles and some classic beefs that tell the story of how this art form evolved. What made this battle feel different — and maybe even tragic — to you? What did you feel was at stake?

I was there at the Source Awards when the s*** really hit the fan in 1995. And I was there in 1997. That was a “What now?” moment for hip-hop — Tupac and Biggie, embroiled in a battle. I've never seen a battle in which it ends well.

We're living in a polarizing time. We're living in a time right now where World War III can easily break out at any moment. We're living in a time when civil war can break out at any moment in the United States. We're living in a time where the uncertainty of something jumping off is just in the air. You know what I'm saying? For me it's like, I've seen this movie before — and I'm triggered. The aftereffect of Tupac and Biggie was just a 30-year travel into darkness.

And this is not to say that quality has gone down. Look, of course I don't think hip-hop is dead. If an MC like Little Simz, which people rarely talk about … I don't think people give enough attention to Griselda: Westside, Conway and Benny. Or even, like, Tobe [Nwigwe], Mick Jenkins, Errol Holden, even Denzel Curry. There's so much quality, dope stuff out there that just goes unnoticed and unchampioned.

So much of the book is you admittedly playing catch-up to each era of hip-hop innovation. First, you kinda cram to understand it, then you finally accept it, and eventually you grow to appreciate it. But there's always something at your core that you're resisting. Is it change in general? Is it the slide into commercialism over time? Are you a hip-hop conservative? What is it that you tend to be resisting when you initially hear something that you don’t like?

As an adult, I at least know where my default level lies. When something is jarring and rubs me the wrong way or doesn't make sense, then I'm smart enough to know this is the next phase of what's happening, creatively. When something stops you in your tracks and is just out the norm, it does that to you. The night that [pioneering radio DJ] Lady B premiered "Rebel Without a Pause" by Public Enemy — it's, like, July of 1988 — we’d never heard a song like that in our lives. Sonically, that song encapsulated all the angst and the furor that we all felt.

But then I remember when The Chronic came out by Dr. Dre, and everybody was enamored with it, and I kept saying, “Wait a minute — if you just take the vocals away, any R&B singer could sing on top of this.” I had it in my mind that hip-hop had to have a certain sonic dirtiness to it — the kind of sonic dirt that the Jungle Brothers were using on their first album, Straight Out the Jungle — a very lo-fi, dirty sound. My question to my peers who ragged me because I didn't like The Chronic was, isn't this what we're against? This is us trying to be mainstream radio. It took me 15 years to finally give in and be, like, that damn Dre’s a genius — because as a DJ, when you play a Dr. Dre production, the mixing of it is so immaculate and so perfect that it's made for that environment.

When Yeezus came out, I instantly was, like, “self-indulgent” — I was panning it because my first listen to the album was on my MacBook Pro speakers, which, I'm borderline certain that’s not how Kanye wanted me to hear that record. Now turn to him at Madison Square Garden, and my seats were right on the speakers. It was like the equivalent of a sonic colonic, that's how much bass was coming out of those subwoofers. Suddenly I was, like, “Oh, this is why he doesn't have drums on the record.” I realized that Kanye intended this album to be heard in a stadium.

Oftentimes, when I just don't feel comfort, usually that means it's going in the right direction. So perhaps my disdain for where we are right now — I still do not want to see bloodshed, so I kind of stick by my position — but I will also say that hip-hop is still finding itself, still defining a generation and all those things. And with today's music, you’ve just got to adjust to it.

It feels like you've spent a lot of your life wincing when hip-hop refused to take the high road. When it's evolved in ways that you saw as regressive, has it ever made you question your place in it?

I believe, above anything, when I leave this earth and you’ve gotta figure out what to put on my byline, I call myself a creative. And sometimes you have to leave something to appreciate it. When J Dilla passed away, I didn't want to throw the baby out with the bathwater, but hip-hop really wasn't the same for me after he left. I started to take interest in other things that still kept me creative.

I never, ever left hip-hop. Was I as passionate about it? I don't think anyone has the same passion for anything. It's almost like your life partner: Those first seven months, you're obsessed with that person. And then, 20 years down the line, there's another degree to that relationship that defines it; the adhesive that holds it together might not be as passionate as at first. The way that I felt about hip-hop in ‘88, when every week a new album was changing your life, I don't feel that way now. But I definitely know that there's people that have that same passion as I did.

So, do I truly feel like hip-hop is dead? No, I don't. However, I do believe that the landscape and the rules have changed. And some of its participants don't know it.

What’s changed for the worse?

Creating on defense. I don't know if that's a fun thing. I think all these [Kendrick vs. Drake] songs are defensive, because it's, like, you’ve got to prove — not even to yourself, but to the world’s definition — your worthiness of being here. And then what's underneath that hood? I gotta prove my manhood. Or, I gotta prove I'm smarter than you. Or, I gotta prove I'm more successful than you. I gotta hit your weak spots, drive-by shooting style — I don't care who I hit.

I’ll ask you, what’s your opinion of it?

Of the beef, overall? I think what you're describing right now sounds like what a lot of rappers are driven by — even when they're not beefing. Think about how many artists’ songs you hear where they’re obviously speaking to some unknown, anonymous nemesis.

Like who’s the Sucker MC that Run-D.M.C. is rapping about?

Right, you know what I'm saying? It seems like there's this perpetual battle. I don't know if it's the man in the mirror that cats are battling, or … 

So, André 3000, when New Blue Sun came out, we were having a conversation about where he was, creatively, and what motivates him and all that stuff. He’d said something to the tune of, he's only motivated when someone doubts him. And my first question was, “Dude, have you met yourself? Who's doubting André 3000?” He's, like, “Well, that's exactly the point.” And I said to him, “So are you playing provocateur right now? Is this your version of the wet willy? Are you …”

Trolling us?

Yeah. I kept probing: “I don't know anyone who doubts you. You're so critically acclaimed. Do you believe us when we tell you that you're a genius?” I'm forgetting his immediate response, but the fact that he left a seven-second pregnant pause told me that he might have imposter syndrome issues, issues with how we built him up to be one of our gods. So I said, “If we come out the gate and say, ‘Yo, man, this album absolutely 112,000% sucks,’ or, ‘You're a horrible rapper’ — then you would have felt motivated to go back in to prove that you are indeed the man?” And I believe he was leaning towards a yes. So the teachable lesson is, let's just pan André 3000 so he can come back. [laughs] No, I'm playing. I get that this is a blood sport. But I also know and have witnessed and experienced creativity when it didn't come from this need to prove oneself.

Well, you asked me what I think about it, and I want to answer your question. As entertaining as the music is at times, I don't like seeing Black men battle each other for the sake of what feels like commerce. I don't like the “I'll destroy you by any means” thing that happens on a world stage. It feels like there was a particular time in hip-hop where we were all in the kitchen.

We were in our bubble together.

Yeah, Black folks at the kitchen table.

Well, yeah, the mainstream press was not talking about “The Bridge is Over.” I don't ever once recall seeing “Takeover” or “Ether” in Time magazine. It's different when it's in the social media hypersphere.

It feels like it becomes this celebration of Black pathology — or an attempt to label it as such — by those outside the culture. So that part of it, I don't like. But I also never want to get into any kind of respectability politics, where we feel like we’ve gotta button our shirt up to the top button when everybody’s watching.

Right, so if I do have a regret, had I known that my word would have been clickbait — I'm very much against performative respectability politics and [clears throat]: “One should not curse!” I hate that person. The whole pound cake thing. I loathe it. And that's why I'm kind of eye-rolling, ‘cause now I've just been placed in that particular [context]. Because I've also gotten praise, like, “Yeah, Quest, I agree with you!” And then I'm, like, wait a minute, you're also the person that thought that hip-hop was trash to begin with. Don't let my rant be your excuse to justify why you always thought that hip-hop was trash.

In an interview with HipHopDX, you said The Roots have been working on your next album for six years — and that interview was two years ago. Are you still working on that album?

One of the prime reasons activity stopped in terms of an actual Roots product was the transitioning, the death, of our manager/producer — the adult in the room — which was Richard Nichols, the gentleman that's been the Billy Preston/George Martin to our Beatles for our entire career. When he died of leukemia in 2014, that kind of put Tariq [Trotter, aka Black Thought] and I in a position. We’d always been used to being in the back seat while he drove. Even in the communication, I’d go to Richard, like [whispering], “Yo, man, I don't like that verse. Could you make him do the s*** again, please?” Tariq would go to him, “Yo, man, I ain't feeling that track. He gotta do something different with the bass line or something.”

He was the middleman.

Exactly. Most groups kind of implode. The Beatles imploded after nine, 10 years. And that's The Beatles. Tariq and I are in our 37th year together as friends — 31 as business partners. Both he and I had to do a lot of growing up: levels of therapy, levels of self-help, levels of communication more than anything. This is maybe our third or fourth reset.

And this is not to say that we were inactive: We were actively making an album, since 2015. Ideas always come when you are not actively doing music for a long time. When I was working on the movie and working on a book and working elsewhere, suddenly you start getting these ideas again. You're trying to ignore it — like, I had to concentrate on just writing this book or scoring this film or whatever. And then inspiration always hits you, like the temptation of going outside of your relationship. From, like, 2018 till maybe six months ago, every idea was better than the last idea. So there's maybe a collection of 300 songs and demos that were just mind-blowing, one after the other. At the top of this year, I put the flag down and said, let's commit to these 14 songs, and promise that no matter how many other ideas we get, these 14 songs come out at the end of this year.

Are you saying The Roots are putting out an album this year? Or is this going to go down like that HipHopDX interview?

No, no, I promise not to kick the can down the road. I'm not going to say a few months from now. But, yes, we are finishing this record.

In an interview that he did shortly before passing, Richard Nichols laid out The Roots’ artistic mission as, “How can we help define what it means to be a Black person in the 21st century?” In some ways, as this conversation is proving, that almost seems antithetical to what hip-hop has become. Is that still the goal for you, and for y’all?

It's the goal for me, personally. Especially having spent two years doing this Sly Stone [documentary]. Without giving too much of it away, it's less about Sly Stone's life than about trying to answer the question, why do we self-sabotage?

Do you see him as a tragic figure more than a heroic figure? What is your angle going to be?

When I started this project, I asked my mother, what do you think happened to Sly Stone? And everyone's take is always the same, which is what incenses me about Nancy Reagan’s “Just Say No” campaign. My mom's answer was basically, he was someone that became a superstar and was super-talented — and then he chose drugs. And it's not that. We're trying to tell Sly's story using the empathy angle.

I chose Sly because of Sly's level of success, post-Civil Rights era — post-King, post-Kennedy, post-Jim Crow, post-Reconstruction, post-slavery, post-our experience in America. What happens when you get everything you want? And we can apply this to the hip-hop hustle ethos. Why do we still find ourselves self-sabotaging? Why are we choosing cocaine? What are the reasons? Why do we need to self-medicate on cocaine, or alcohol, or food, or gambling, or overworking, or sex, or cutting ourselves, shoplifting. Like, there’s so…

So many vices.

Right. My question in this project is to find out, is Black success as burdensome as Black failure?

Some of the people that I’ve tested this theory on say, “More than Black people go through this. I go through this every day.” But you don't have the generational obligation to save everyone. If you're given a winning lottery ticket to save yourself, and you can only save yourself, you will be miserable — because you're instantly going to think about, you know, there's a community. There’s a relationship we have where I [equals] we, and your success is my success. Can you take your cousins with you? Can you take your best friends from high school with you? Can you take your family with you? Can you trust people?

I battle with it every day. I'll go to an event in which I'm one of the lone Black people, and I instantly start telling myself, Oh, man, you're selling out. Do you belong here? Should you belong here? Are people shaking their heads like, “See, you don't belong in these spaces”?

This is like survivor's guilt, but taken to the next level.

Yes, and this is why we self-sabotage. That’s what I'm trying to unpack — centuries of trauma that survivors feel, centuries of burdens that people feel when they're designated “one of the good ones.” Trust me, I'm quadruple-aware that there's this perception of, “Questlove, he's one of the good ones.” And that's a mark of shame for us —it's almost like I need to let motherf*****s know that I come from West Philadelphia, you know? So it's a lot to unpack, man.

You are kind of an anomaly in a lot of ways — you're this obsessive music nerd who's driven by critical acclaim more than commercial success.

Used to be [laughs].

Well, you’re also an artist who obsesses over what it takes to make a pop hit. Would you be willing to sacrifice one for the other? Is that a choice that you could live with? Is that something that you're trying to do in this next Roots album, potentially?

So you already found one of my Achilles' heels. This is what's taken the record so long. Something happened in the pandemic: After two weeks of losing my mind — Am I coming or am I going? Am I living or dying? Who died this week? — I found a way to be creative. Because I needed to be creative in order to not go out my mind.

I started DJing. But it was different in the pandemic: I'm not DJing to make people dance in their living rooms. I'm trying to comfort people. If anything, my song choices during the pandemic were closer to the music that I actually like. I express this in several of my books — the war between what I think is good music versus bad music, what I think is effective versus non-effective. I think I've clocked somewhere between 20 and 30,000 Gladwellian hours of DJing, which has now made me extremely aware of how a song works and how a song doesn't work.

When we first started The Roots, the genesis of the energy that Tariq and I created together was based on doing stuff off the top of our heads: We just went on the streets and started playing. And somehow, that aesthetic bled over to how we create music. Those first five or six Roots albums are a result of just messing around. It was the whole naivete of, I don't know what a real hook is.

I hate to disappoint people, because I think that people tend to think that we had a stance that we're not creators of commercial music. I assure you that it is way harder to write “Where Did Our Love Go” or “September,” by Earth, Wind and Fire, or “Shake It Off” by Taylor Swift. It's harder to write what we dismiss as bubblegum pop music. I can knock out 12 Miles Davis' Bitches Brew, On the Corner, artistic, left-of-center songs in my sleep, mainly because I don't know the science of how music works and why pop songs work. Now, I'm so aware of it — I've DJed so much in the last five years that it's starting to affect all of my creativity.

So this is going to be a very different Roots album.

It's a way different Roots record.