Episode 1666 - Questlove

Summary

WTF with Marc Maron Podcast: Episode 1666 - Questlove

Release Date: August 4, 2025

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Introduction and Background

In this episode, Marc Maron engages in an in-depth conversation with renowned musician, producer, and filmmaker Questlove (Ahmir Thompson). The discussion delves into Questlove's multifaceted career, his contributions to music and film, and the personal challenges he faces as a celebrated artist.

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Questlove's Career and Achievements

Marc begins by highlighting Questlove's impressive resume:

• Founding Member of The Roots: Questlove co-founded the legendary hip-hop band, The Roots, known for their innovative approach to music.
• Grammy and Oscar Wins: He is a six-time Grammy winner and won an Academy Award for the documentary Summer of Soul.
• Emmy Nominations: Questlove is nominated for three Emmys, including for his documentary Sly Lives AKA the Burden of Black Genius.

Marc Maron:
"Quest is one of those guys that you're like, where do I start? And he kind of goes, you just kind of sit down and he'll take it from there." (Timestamp: 01:58)

Questlove:
"Thank you, man." (Timestamp: 86:57)

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Exploring Sly Lives AKA the Burden of Black Genius

Marc praises Questlove's documentary, emphasizing its depth and the way it uses Sly Stone's story to explore broader themes in music and culture.

Marc Maron:
"he kind of goes into his work, his psyche, his time, it's the people around him. It was kind of amazing how big he was." (Timestamp: 05:00)

Questlove:
"It's all sourced. He started out as the classical prodigy and choir church leader by the age of six." (Timestamp: 66:27)

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Personal Reflections and Challenges of Success

Both Marc and Questlove discuss the emotional and psychological burdens that come with success. Questlove shares his experiences with anxiety and the internal conflicts that arise from public recognition.

Marc Maron:
"But what's weird is that he, in 62, as a radio DJ, will basically raise the counterculture tweens that we will later know as hippies. So all those hippies that you see in, like, the Summer of Love, 67, 68, they're in 1962. They're 12 and 13 listening to Sly on the radio." (Timestamp: 66:52)

Questlove:
"I'm having a lot of anxiety because so much is going on and you know, I'm not at that level where I'm winning Oscars or anything. But it's uncomfortable for me and I just talked about it for the podcast." (Timestamp: 71:40)

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The Intersection of Art and Commercial Success

The conversation shifts to the balance between artistic integrity and commercial success. Questlove reflects on the challenges of maintaining authenticity while navigating the business side of the entertainment industry.

Dale:
"I used a story to tell my story because, you know, I figured we might as well show the first domino falling." (Timestamp: 77:18)

Questlove:
"At some point you have to delegate. At some point you have to manage, you know, the situation so you can execute how you want to execute." (Timestamp: 80:57)

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Mental Health and Therapy

Questlove opens up about his mental health journey, discussing how therapy has helped him manage the stresses of his career and personal life.

Questlove:
"I've done enough work in therapy to talk myself off of like many a ledge." (Timestamp: 72:21)

Dale:
"It's hard to bask in the glory of comfort when even now, like, what slide go through." (Timestamp: 51:10)

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Legacy and Influence

Both guests reflect on their legacies and the impact they've had on their respective fields. Questlove acknowledges the influence of his peers and the importance of honoring musical pioneers like Sly Stone.

Questlove:
"I'm so glad we got it in, man." (Timestamp: 86:57)

Dale:
"Hip hop is Warhol's version of taking everything that's before you and recontextualizing." (Timestamp: 79:39)

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Conclusion and Final Thoughts

The episode concludes with mutual appreciation and acknowledgment of each other's contributions to art and culture. Marc emphasizes the heavy weight of success and the ongoing quest for personal fulfillment.

Marc Maron:
"Who are we? Do we deserve it?" (Timestamp: 87:14)

Questlove:
"It's important for me to know this because, you know, right now I am pivoting to scripted." (Timestamp: 84:15)

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Notable Quotes

• Marc Maron:
  "Everything then becomes nostalgia. Everything becomes just a YouTube video." (Timestamp: 05:30)

• Questlove:
  "The podcast brings people, you know, an intimacy with, with talented people that ranges the full spectrum of experience." (Timestamp: 82:46)

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Key Takeaways

• Artistic Integrity vs. Commercial Success: Balancing personal creativity with the demands of the industry remains a central theme.
• Mental Health: The psychological toll of fame and success is a significant concern for artists.
• Legacy Building: Both Marc and Questlove are focused on creating meaningful and lasting contributions to their fields.
• Interconnectedness of Genres: The discussion highlights how different musical genres influence and transform one another over time.

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This episode offers listeners a profound exploration of Questlove's career, the complexities of success, and the enduring impact of influential artists like Sly Stone. It's a candid and introspective conversation that resonates with anyone navigating the intersections of creativity, fame, and personal well-being.

Transcript

[Marc Maron]

Folks, we've waited 15 long years for King of the Hill to return to our screens. And now the classic series has arrived on Hulu. Newly retired Hank Hill and his wife Peggy return to their Texas home from the Middle east and realize things look a little different. Bobby's all grown up running a German Japanese fusion restaurant in Dallas and still fumbling through his feelings for Connie. Boomhauer continues to be a hit with the ladies as he takes his business online. Bill's really let the years get to him. And D is, well, you know, Dale is just Dale. Arwen sure has changed as Hank and Peggy try to find their bearings again. But one thing's for sure, the alley guys are right where Hank left them, beers in hand. And Alamos on ice. Same hill, new day. Yep. A whole new season of King of the Hill is now streaming on Hulu and Hulu on Disney plus for bundle subscribers, terms apply. Okay, folks, today's episode is sponsored by Squarespace. Which is the best way to showcase your stuff online. Your art, your podcast, your crafts, you. By helping you make a customizable website. Now, using blueprint AI, build your whole website in just a few steps. Then choose whatever features you want to get the most out of your site. Just like we do with wtfpod.com check out squarespace.com WTF for a free trial. And then use offer code WTF to save 10% off your first purchase of a website or domain. That's squarespace.com WTF offer code WTF. All right. Okay. Yeah, let's do it. All right. Let's do this. How are you? What the fuckers? What the fuck, buddies? What the fuck, Nicks? What the fuck wits? What the fuck? Oh, Kratz.

[Questlove]

What's happening?

[Marc Maron]

I'm Marc Maron. This is my podcast. Welcome to it. How's it going out there? How is it going out there? Oh, my God. New York was fucking crazy. I did so much shit there. So many different media hits. Old timey media hits. I went to CNN in the morning and it was almost like there was no one there. It was kind of depressing. The building was kind of empty. Then I went over to the Hearst building and did a thing for Esquire and a thing for Men's Help. Same thing. The building just seemed empty in these offices. Just a lot of empty desks. It was just. I guess that's just where things are at. Was kind of saddening. But oddly, that Hearst building is pretty amazing. And that Hudson Yard building, too, was where CNN is. And some other stuff I think HBO's down there now too. Pretty stunning buildings I've gotten kind of. Sometimes I lock in to buildings I lock into public spaces. And I gotta tell you, man, I can't shut up about Kit Kemp. Yeah, I will tell you about it, I guess in just a second. But today on the show I'm gonna talk to Questlove. He's the co founder of the Roots. He's a six time Grammy winner and a best documentary Oscar winner for Summer of Soul. He's nominated for three Emmys this year, including one for his documentary Sly Lives AKA the Burden of Black Genius, which I watched and I gotta say, it was great. It was great. You know, Quest is one of those guys that you're like, where do I start? Where do I go? But he kind of goes, you just kind of sit down and he'll take it from there. But that Sly Stone documentary was mind blowing. You know, Quest just used him as a portal to explore an entire time period and the impact Sly had on all of music. And you know, as time goes on and a guy gets the reputation of being a fuck up or a guy that just burned it all down, which so I. Did you forget that the phenomenon of Sly Stone was much bigger than the few songs you might know. And the way Quest kind of goes into his work, his psyche, his time, it's the people around him. It was kind of amazing how big he was. And everything just kind of goes by the wayside, you know, everything becomes nostalgia. Everything becomes just a, a YouTube video. Everything becomes, I don't know, just sort of like, hey, that's behind us. I guess a lot of comics are doing this Riad Comedy Festival brought to you by the people that brought us 9 11. Okay. I guess that's nostalgia. Getting their check signed by the guy who buzz sawed a journalist and put him in a piece of luggage. Yeah, I mean, you know, look, right? Money's money, right? I don't know, does anything matter anymore? Back to business, folks. Back to business. I was talking about Kitkamp, first of all. I can't shut up about Kitkamp. And sometimes I get very. I get kind of connected to public space or private space or whatever, but I guess she co owns the Fermdale Hotels and I stayed at the Crosby in New York and I love that fucking hotel. It's a little pricey for me, but we got the HBO rate and they kind of picked up part of it. And I just. The times I've been there. One time DreamWorks put me up there And I stayed at a suite. And I never understood interior design until I stayed at that place. I mean, it was just everywhere you looked, it was just mind blowing. I feel like I've talked about her before, and I don't know that there's any reason to talk about her. I mean, she doesn't need promotion, but every time I stay at one of her hotels, like the Crosby, I just wander around going, like, look at these chairs. It's a totally different fabric on this one than the other one. The walls, the wall treatments have fabrics. Everything's different colors. It seems like it wouldn't match, but it's fucking genius. The aesthetic is, like, totally unique, but grounded in something kind of traditional, almost English. But the colors and the fabrics and the wall treatments and the things on the wall and the chairs and the fucking table. I'm like, I'm having people go over there. I swear to God, when I was over there, Bowen Yang came by because I interviewed him. You'll hear that. But after we talked him, like, let me show you around the hotel. Like, it was like my fucking house. Every room is different. The headboards, the wall treatment, the fabrics on the couches. I can't even look. I'm not telling you to stay there. Just look her up. Look up Kit Kemp Hotels and just look at those interiors and tell me that your fucking mind isn't blown. Just tell me that. Would you Tell me it? This is an ad by BetterHelp. These days, it feels like there's advice for everything. Cold plunges, gratitude journals, screen detoxes. But how do you know what actually works for you? 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Okay, so the screening at the 92nd Street Y was great. A lot of fans came. I watched my special again on a big screen. Obviously the special is out now on hbo, and HBO Max seems to be getting a lot of good features feedback, which I'm happy about. I like hearing about it, but I do like. I like when real critics assess my work. People have really a depth of. Of analysis and thought and reference. I, I enjoy reading it. Even if it's not good. I generally learn something. There's a difference between a piece of criticism and a review. A review just picks these points. It's usually slightly stilted or not at all to the writer's point of view, but it's usually only a few paragraphs and you can you kind of tell what their angle is, even if it's a relatively good review, if they're just kind of, you know, going through the paces. But I will say this. The New York Times. Jason Zinnerman did a beautiful piece, not just about the. The special, but sort of about the weaving of the special with what I do on the podcast. And, you know, he's been sort of on top of my shit for a long time. He knows what I do, he knows my work, and he's been there for a long time. But this is a beautiful piece and a real honor to read it. Catherine Van Arendonck over at Vulture, she also did kind of a sweeping piece about me and the special, but knowing my work going back and sort of like making me even look at things a little differently, that's what I like about a good review. And the Atlantic did a very nice piece. Vikram Murthy, again, people who know my work, who think about my work, who can assess it over sometimes decades. I'm not just tooting my horn about good reviews, but these were thorough so I can learning someone else's point of view. When it's kind of laid out there and thoughtful, it's helpful to me. I don't know how it lands. I don't know how people frame it. I know the way I think it should be framed generally, but by watching it for the umpteenth time. Well, not that many, but probably the fourth or fifth time in a live audience on a big screen, that's when it starts to break down for me. I'm like, know. Then it gets nitpicky, you know, But I, I think it. I think it looked great. But afterwards, after the screening Jim Gaffigan moderated a conversation with me and that was fun. It was fun. And I believe, if I'm not mistaken, we are going to put it up for Thursday's show. So thanks for watching it. If you watched it, I know that the Theo Vaughn clip has gone viral. I don't. I'm. I love that bit. I imagine Theo can take it. I don't know. I thought it was pretty good. I thought it was a solid kind of acute busting of balls. But it was a joke and it was funny, so we'll see. But that seems to be getting out there to the right and wrong people. But all in all, when I got home on Saturday, I was wiped out. It was a long bit of press and a long week of press, and I was just kind of beside myself, starting to re. Obsess on, you know, my life on, you know, whatever's, you know, under my toenail, which I think is just a bruise, but I'm probably going to go in and look because people make me paranoid. But now I'm looking at right now. I'm pretty sure I dropped something on there, but I always think cancer.

[Jim Gaffigan]

Yeah.

[Marc Maron]

And my cats. And my cats. That's back to life. Pick your anxiety. Why not just enjoy it? Why not come home the day your fucking special premieres, it's on Friday. And not be a fucking anxious, exhausted, fucked up wreck of a person?

[Jim Gaffigan]

Huh?

[Marc Maron]

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[Questlove]

Man.

[Marc Maron]

That's a lot of. That's a lot of weight, but exciting. This is me talking to Questlove.

[Dale]

This is a full circle. I don't even know if you know how much of a full circle moment.

[Jim Gaffigan]

This is for you.

[Dale]

Yeah, for me. Because your obsession with the snl.

[Jim Gaffigan]

Yeah.

[Dale]

Ecosystem.

[Jim Gaffigan]

Yeah.

[Dale]

I kind of rode your wave into that. Even though, like, I. I believe you're. You're. This particular part of your podcast started, like, 2008. 2009.

[Questlove]

Nine.

[Jim Gaffigan]

Yeah. Yeah.

[Dale]

So I think between. Between the oral history book.

[Jim Gaffigan]

Yeah.

[Dale]

And, you know, a year before your podcast comes on, of course, like, I'm getting lured into the world. Yeah. I'm getting lured into what I call 30 Rock University.

[Jim Gaffigan]

Yeah.

[Dale]

And, yeah, I'll say that your podcast was a really major, major part of my. Like, it was an education. It was a crash course that I needed, and it helped. Oh. In ways you would imagine. Like. And if I'm really honest about it, I think the first person I wanted to know once I was done my part of the doc. You know, there's six docs done for.

[Questlove]

Snl for the music part.

[Dale]

Yeah.

[Questlove]

Is that nominated for an Emmy, too?

[Dale]

Yes, it's nominated.

[Questlove]

What was it, like, 50 years of SNL music.

[Dale]

I did 50 years of SNL music. Also got nominated for the Friday night music concert they threw.

[Marc Maron]

Oh, yeah.

[Dale]

Yeah. At Radio City. What's my third one for? Oh, my God.

[Jim Gaffigan]

Yeah.

[Dale]

They'll kill me, dude.

[Marc Maron]

That's.

[Dale]

Sorry, Disney. Yes.

[Questlove]

That thing is so good, dude.

[Dale]

Thank you. So. Yeah. But when I was finished, I. Even more than trying to impress Lauren and the. And the. Anyone in the 30 rock ecosystem.

[Jim Gaffigan]

Yeah.

[Dale]

I'm. I'm a part of your world, which are the people that are affected by the 30 rock ecosystem.

[Jim Gaffigan]

Yeah.

[Dale]

So I think in my mind I wanted to create something that lived up to the lore and the standard because all the obsessions you had, like, no one was happier about your finally getting to Lauren than I was. I feel like this even way better than you getting chosen in 95. Sure.

[Questlove]

Oh, yeah. No, the journey was something.

[Dale]

And like you, if I'm honest with myself.

[Jim Gaffigan]

Yeah.

[Dale]

I mean, of course I'll say that in 2008 because of the way the Roots operate. The Roots are essentially hip hop's version of Fish or the Dead.

[Jim Gaffigan]

Yeah.

[Dale]

We were a 290 year tour bus living hip hop jam band by our 18th year. You know, I always joke that if you can navigate through the Japanese subway system by yourself without like a label, like, you've been around too much.

[Jim Gaffigan]

Yeah.

[Dale]

Like that's how much we traveled the world where we could just show up by ourselves. Like it was nothing. Then, you know, around that time, we were just wondering, like, is there anything else for us? So when Jimmy had approached us about coming to 30 Rock, I. I kind of think my willingness to risk it all because by that point, year 18, we just got to a Nirvana place, if you will, like financially and. Right. You know, doing all right. Good money on it. Right, Exactly. And why would you, as soon as you get to the mountaintop, want to turn your back in, try something untested? And I think my decision was a very, very slow cook game to just be a musical guest on a show that I've been watching since I was five years old, but none of my. I played none of my obsession cards with. The only thing that gave me away was when the first thing I did was I arrived at Lauren's office with a giant bag of popcorn.

[Jim Gaffigan]

Yeah.

[Dale]

So instantly Jimmy's like, oh, he's a comedy nerd. Because he knows about the. If you know anything about Lauren's atmosphere during SNL season, you know that there's a popcorn machine in his office.

[Jim Gaffigan]

Yeah.

[Dale]

You know, so I brought him a bag of popcorn, which was instantly thumbs up from Jimmy. Like, oh, you, you belong here. But in my mind, I figured, okay, well, come here for a little bit. And eventually got to figure out my way to get up on the eighth floor. So it's kind of weird that I've been a part of SNL's whole system in every way possible, except for the one way I want to be.

[Jim Gaffigan]

Which is what?

[Questlove]

Performing.

[Dale]

Which is just a musical guest on the show. Like, we've, I've. We've backed Three acts on there. I mean, technically, I guess you could say. Yeah, technically. The Roots were the musical guests for the 50th anniversary. But I've been a punchline. I've been on a sketch.

[Jim Gaffigan]

Yeah.

[Dale]

A Weekend Update. I've been part of at least two. Lonely Island.

[Jim Gaffigan]

Yeah.

[Dale]

Cancel Bits or whatever.

[Questlove]

I've never played the next. The Roots.

[Jim Gaffigan]

Yeah.

[Dale]

That's. That's just only because I, you know, I was raised in a really weird household that didn't want me to watch television.

[Marc Maron]

But what was the reasoning on that?

[Jim Gaffigan]

Oh, God.

[Dale]

All right, so, you know, I was. I was impressionable as a kid. You. You remember the old Hawaiian Punch commercials?

[Questlove]

Sure.

[Dale]

Where Punchy.

[Jim Gaffigan]

Yeah.

[Dale]

The Hawaiian native.

[Jim Gaffigan]

Yeah.

[Dale]

Would go up to some poor, sad sucker of a tourist guy.

[Jim Gaffigan]

Yeah.

[Dale]

You know, hey, how about Nazi? So why I'm punching. He just punched his shit out of him with a bunch of fruit.

[Jim Gaffigan]

Yeah.

[Dale]

I. I love that commercial a lot. And unknowingly asked my mom to participate with me as Punchy and her as the. I was like, mom, bend down. Okay. Now I'm saying, how about no? I said, why don't you punch? You say. She said, sure. And cut to them taking the TV away.

[Jim Gaffigan]

That's it.

[Dale]

However, because my parents were musicians, I wasn't allowed to watch tv, but I was allowed to watch pbs, any educational shows. And if it were music, they would wake me up. This is how, like, liberal they were before the 80s. They did a total, like, Flanders Christian turnaround by 82. But from birth until 82, I was born in 71.

[Questlove]

They became born again.

[Dale]

Yeah, well, everyone did, you know. And Donna Summer became a Christian. Like, anyone that. My parents were, like, hip.

[Questlove]

It took a lot of coke to get down the summers there.

[Dale]

Well, yeah. I just think that once you're turning 40. In the early 80s, like, they believed in the original Make America Great Again. Like, right. We need to atone for our sins. Like, everyone became a Christian. Like, once you're saying secular. I hate that term. Once. Once you're a pop singer, whatever. You know, B.J. thomas was on it. Donna Summer was on it. Like the 700 Club or the PTL Club. And now I'm a born again Christian. So there was a. There was a uncool shutdown period that.

[Questlove]

Was called the post disco repentance.

[Dale]

Well, my parents were part of that. And so. But what they would do was in the 70s, like, they wake me up.

[Jim Gaffigan]

I.

[Dale]

You know, I'd have to go to bed every night at 8.

[Jim Gaffigan]

Yeah.

[Dale]

However, if the temptations were on the night show, the Jackson 5 on the Tonight show, most importantly, like Midnight Special will come on at 12:30 on Fridays. Don Kirstner's rock concert was on at 1:00am yeah. Most of Soul Train was a 12 in the afternoon experience for most of America.

[Jim Gaffigan]

Yeah.

[Dale]

In Philly it was a 1am Experience. And so they'd wake me up at 12:30. So I'd go and turn on SNL of which weekend update was like a two segment thing in the 70s. And then Jim Henson's Muppets and then the musical guest would do two songs. I'd watch those religiously. Soul Train comes on at 1 2am back in bed, up for church at 7. That was my life for the first like eight years. So I remember all those SNL.

[Jim Gaffigan]

Sure.

[Questlove]

The early ones.

[Dale]

Yeah. Like I just watched everything religiously from 75 on. So, yeah. I will say that next to you, I was probably your fandom for that institution match mine. That's why I felt like I have to come on this podcast just to get closure. Just to just the bond. Exactly. And get closure.

[Questlove]

But when you took the gig over there, like, you know, given that you guys were at the top of your game, I mean, was there sort of a band discussion that got heated?

[Dale]

It wasn't heated. The thing is that, you know, the Roots, Tariq and I started the roots in 87.

[Jim Gaffigan]

Yeah.

[Dale]

And we were grouping name only. And the thing was, like, at our high school was like fierce competition. Right. Every. Which high school is that? The Philadelphia High School of Creative. And this is what year I came in.87, graduated 89. So by, by this point, boys to men.

[Questlove]

So hip hop was competitive as hell?

[Dale]

Oh, very much so, yeah. Very much so. Like it? For me, that was one of the first public schools I went to.

[Jim Gaffigan]

Yeah.

[Dale]

Like previously before performing arts, my parents had me in these like college prep, you know, future Jeopardy Contestant.

[Jim Gaffigan]

Yeah.

[Dale]

Type of schools.

[Questlove]

Because he showed proclivity in the memorization area.

[Dale]

Exactly. I, I was, you know, the kid that uses the, the nine syllable world and it gets tossed in the trash can like a second later. Like, nerd. Yeah, yeah, no, that's. And I get taught that was me. So at the time, like anyone who's running jazz right now, like, went to my school, Boyz II Men, were pretty much at the at. Came out the gate as stars. So Tareka and I really didn't make noise until maybe two years after we graduated. We were busking on the streets of Philadelphia, got a deal.

[Questlove]

Busking how? Like, what was, what were you Playing.

[Dale]

So, okay, so my dad's plan was for me to either go to Curtis Institute in Philly or Juilliard or the New School for Jazz. And when I did my Juilliard new School audition, I took the train up. Tariq came with me that weekend. I had a friend that lived up there, so we spent the weekend in New York. And when we came back home. This is like the black version of the Bugle Boys jean commercial.

[Jim Gaffigan]

Yeah.

[Dale]

The world's most beautiful girl comes up to me and says, excuse me, are you the drummer in the Spike Lee Levi's commercial? And my dumb ass said, no, I'm not. And she was like, oh, okay. She walks away all sultry, and Tariq's looking at me like, why would you tell her that? You wouldn't. Like, you know, like, why did you get her number? She. Okay. Because Boyz II Men had chosen me to be in their very first video.

[Jim Gaffigan]

Yeah.

[Dale]

Their first single was Motown Philly. So I was in that video playing. Right. What I should have said was, no, you're thinking of. I had a very distinctive hairstyle similar to what the kid wore in the Spike Lee thing. So it was easy to get the two of them mixed up. But what she wanted to say was, are you the drummer in the Boys to Men Motown Philly video? And then she could have been wife and kids or whatever, but whole different life, right? Instead.

[Marc Maron]

She.

[Dale]

I said, no, she got off the train, and Tariq was just, like, ragging me all weekend, like, you dumbass. Dumbass.

[Jim Gaffigan]

Yeah.

[Dale]

So the next day, crash out at my crib. Next day, Soul Train comes on, and that commercial comes on, and we had the eureka, slow motion discovery. Like, why don't we do that? And so literally two hours later, I grab buckets in my drumsticks and we go to south street in Philadelphia, which is, like the East Village or What's the beach in California where everyone.

[Jim Gaffigan]

Venice.

[Dale]

Yeah, like, Venice Beach. Like, a place where population is. And counterculture.

[Questlove]

So you're playing the buckets.

[Dale]

I play the buckets. And he rhymed for about an hour straight. And if we don't make $120, then that's the only time we'll ever do that. Then it becomes. Hey, remember that time we.

[Questlove]

Yeah, we did that dumb thing.

[Dale]

Yeah. We went on South street, made 40 bucks each. Like, but we made $120. And it was like, we're rich. Like, that was date night money.

[Jim Gaffigan]

Yeah.

[Dale]

So then it was like, do we do this next week? And the difference between doing this next week Was. I told one of my friends in jazz class, like, yeah, man, I. You know, I went busking and whatever. He said, whoa. You did? Can I. Can I join you? Yeah, I don't care. Because he had a car. He had. Josh Abrams. He's like a big deal in the jazz world now. He had a large.

[Marc Maron]

I think I saw him.

[Questlove]

What's he play?

[Dale]

He's an upright bass player.

[Questlove]

Yeah. I think I saw him up at the. At Dizzy's Lounge.

[Jim Gaffigan]

He.

[Dale]

Yeah, Josh is a thing. Yeah, he's a thing. So he shows up to my house with his upright bass.

[Jim Gaffigan]

Yeah.

[Dale]

And I grabbed my buckets. He's like, whoa. He's like, why are you bringing your buckets? Get your real drums. And I'm like, man, my. My dad's going to kill me. He's like, well, your dad's away for the weekend. Like, he's not going to know. I was like, yeah, you're right. So then I took my drums out, and that's when the Roots as you know it now really started to exist. Because the second we did that, then suddenly the doors were open. Whereas, like.

[Questlove]

You mean guys who want to play.

[Dale]

Yeah. Like, we will, for the most part. We would play on south street for four hours.

[Jim Gaffigan]

Yeah.

[Dale]

And then it's guaranteed that somebody. There's five colleges in Philly, so somebody from Temple or Upenn or Drexel or St. Joseph will come to us, give us a card and say, hey, play our kegger for 75 bucks. A lot of.

[Questlove]

For jazz.

[Dale]

Well, a lot of. And this is the part that's sort of cringy. We would get a lot of. Well, I don't like rap music, but I like you guys. So it was kind of like a reverse Rudolph the Red Nosed Reindeer where we got to. The odd guy out gets suddenly to play. Like, our flyer was for J.C. dobbs. I looked at it. Nirvana will come to do that. And this is a club. This is like preteen spirit. Nirvana.

[Questlove]

Like Bleach.

[Dale]

Yeah. And like, literally the lineup is like the future of music right now.

[Jim Gaffigan]

Yeah.

[Dale]

We got to play clubs that your average Philadelphia, especially in hip hop, like, there was no outlet. So playing on the corners was like YouTube for us. Yeah, about a year of that. Then we get into the craziest bidding war ever, and we wind up choosing Geffen Records in 93.

[Questlove]

For the first record.

[Dale]

Yeah, for our. Well, I mean, but our first album was our demo. Our second album was like our major label debut.

[Questlove]

The demo was.

[Marc Maron]

That was Origin Organ Organics.

[Questlove]

Yeah, Organics and that was. Did you want that released?

[Dale]

We didn't know. Like, we. We made a single and we had like an eight hour session in the studio. We made the single in 45 minutes and it's like, well, what else? You got started making up songs and next thing you know, we just had an album's worth from our busking days. A gentleman named Jamal Atene Takuma. He's an avant garde. He's part of the kind of the blackrock collation of Vernon Reed. Living color.

[Jim Gaffigan]

Yeah, yeah.

[Dale]

Progressive jazz. He did some festival in Germany and got a. Had a budget which allowed him to bring musicians from around the world. So he's like, come to Germany. So we decided to really capitalize on this and turned those slew of songs into our first cd, which also turned into our demo for labels. So once we get back from Germany, it was just one gig. We made it like.

[Questlove]

It was like, oh, how many in the ensemble?

[Dale]

Initially, I'll say that core roots. By this point, we were a foursome. It's like a bass player, a drummer, and two emcees. Eventually became five people. A gentleman named Scott Storch, who, you know, pretty much wrote the. All the hits for the 90s, you know, for Eve and. Yeah, and everyone. He was our fifth member. So from that demo alone, got the attention of like eight record labels. And then we chose Geffen. And then something catastrophic happens in April, which is the death of Kurt Cobain kind of pushed us into panic mode because we chose Geffen1 for the. @ that time, they had like an unlimited budget. You know, it's like Nirvana.

[Jim Gaffigan]

Yeah.

[Dale]

Guns and Roses. Aerosmith.

[Jim Gaffigan]

Yeah.

[Dale]

They were making billions. And so they started a black label division. And first Aerosmith had went back to Columbia.

[Questlove]

And then was that like multi, that billion dollar deal forever.

[Dale]

And then it was obvious like Guns N Roses wasn't going to have a follow up. To use your illusion.

[Jim Gaffigan]

Yeah.

[Dale]

Anytime soon. And then April, Kurt Cobain happens. And my manager was like, I get the feeling that they're gonna drop the entire black department before this thing even starts. Yeah, if you remember the movie Ghost.

[Jim Gaffigan]

Yeah.

[Dale]

The way that Swayze convinces Whoopi Goldberg to go to the bank to close an account.

[Marc Maron]

We.

[Dale]

They had so much money that we basically controlled our budget. Like, we didn't have a staff or anything. It was like three or four people, not a full staff. So we had the credit cards. And so basically when we turned in our album, we closed our account and we stole our own money. And we decided we were going to Pull a Hendrix. And so we brought eight one way tickets to London and we lived in Europe for about two years. We wanted London to be our hub.

[Questlove]

We were trying to avoid them coming after the money.

[Dale]

Well, no, we like. By 93, the venue structure for bands had completely shut down.

[Jim Gaffigan]

Yeah.

[Dale]

Like bands were becoming a novelty. It's not. I mean by then, you know, 93, there was still like grunge and rock was still active. But you know, by the time we got a deal, The Roots were one of five black bands left. In the 70s there were hundreds. And now we were one of the.

[Questlove]

Last five because it had all shifted to hip hop.

[Dale]

More. Well one economic wise, it's easier to control a solo artist.

[Jim Gaffigan]

Okay.

[Dale]

Really? For black music, the downfall had it happen in the 80s. Michael leaves the Jacksons, Lionel leaves the Commodores. Cameo started off as 17 man group, now they're a trio.

[Jim Gaffigan]

Yeah.

[Dale]

The point is this is whittled down set of four or three members and now they're doing pop music. So there was, there was something that happens in the 80s in which all the funk groups, all the soul groups, all the, all the captains of those teams go solo and they go pop. And so. And the idea of a band just wasn't an appealing thing. And economically what was the model for that though?

[Questlove]

What was the pressure on them to do that? Who started. Was that a post disco thing too?

[Dale]

Like to.

[Questlove]

To separate them.

[Dale]

Okay, so in. In a kind of Malcolm Gladwillian explanation.

[Jim Gaffigan]

Yeah.

[Dale]

Way I'll say that a lot of our 80s icons were born in the second half of 1958.

[Jim Gaffigan]

Yeah.

[Dale]

Madonna, Prince, Springsteen, Jackson, all you know, in 1958 born. I will say that Michael's probably the perfect example. Where once Jackson 5 hitting 69, he's 11, but they're playing it like he's 8.

[Jim Gaffigan]

Yeah.

[Dale]

So he's precocious and smart enough to be an 8 year old. That has the wisdom of an adult.

[Jim Gaffigan]

Yeah.

[Dale]

But he's also innocent enough to not be threatening. He's not. Hide your daughters. Yeah, threatening. So basically the Jacksons were the first group to truly enjoy the accolades and whatever was denied to whoever came before them because of, you know, like again, Chuck Berry's not able to sleep in the hotels or eat in the restaurants. Right, Exactly. So the timing of Thriller coming. When people speak of Michael's off the Wall album, it's the quality of it. Oh man, this is amazing. Record the, the productions and Quincy Jones just da da da was. People think of Thriller. They talk about the quantity, how many wars did it win? How much money did he make?

[Jim Gaffigan]

Yeah.

[Dale]

How many copies to sell? And that sort of starts the wheel turning and everyone that, oh, I can make money and make living and da da, da, without these guys. Yeah. And there's a diminished return thing. And I'm not trying to paint Thriller as thrillers. You know, in hindsight, even though Thriller changed all of our lives.

[Jim Gaffigan]

Yeah.

[Dale]

I would almost be in the middle and say did more damage than good. Yes. It was revolutionary and changed everything. Changed videos, change marketing. But then it became the. The carrot on a stick that even he, himself, Michael, couldn't the bar to outdo. Right. And then we'd see how that ends. You know what I mean? And so I'll say for the most part.

[Jim Gaffigan]

The.

[Dale]

The idea of black musicianship really just started not to matter as much in the late 80s.

[Questlove]

Isn't that crazy? Because, like, when did you. But like starting out in. In jazz and I know you started out as a kid, but I mean, was the destination like how you did start with your dad? Right.

[Dale]

So I started out in doo wop. Right. My dad. My dad was a doo wop legend that was on Chess Records. So he had. His. His group was LeAndrews and the Hearts. They. They were. They had like three regional hits.

[Questlove]

Doo Wops made a big, big impression on a lot of people.

[Dale]

Well, I meant that's the thing. Like by the time the 70s came around, the first wave of nostalgia period.

[Jim Gaffigan]

Yeah.

[Dale]

American Graffiti, Shana not playing.

[Jim Gaffigan]

Yep.

[Questlove]

Right.

[Dale]

At Woodstock, Laverne and Shirley, Happy Days, Greece. So my dad was instantly on the bandwagon of.

[Questlove]

He.

[Dale]

He retired in 1965. He met my mom, they opened up a clothes boutique. And then his old manager called back. It's like, Lee, you'll never guess this. The 35 year olds today still like the music from when they were 12.

[Jim Gaffigan]

Yeah.

[Dale]

You can go back on the road. And he was like, get out of here. I can't do that. Once there was enough safety for him to shut down his clothing business that he had with my mother. Then it's like, oh, I can actually make a living as an adult doing the stuff I was doing when I was a teenager.

[Questlove]

So being exploited, probably.

[Dale]

Well, yeah, I mean, not exploited.

[Questlove]

It's a singles business, right?

[Dale]

Well, it was a singles business, but he pretty much. His market was for the Northeast. That was very big for doo wop. So we always had the Catskills. There was a big market in New England.

[Questlove]

Kind of started in Philly, right?

[Dale]

Yes, yeah, started in Philly, but then there's also New York. Yeah, Catskills. Right. New England, Atlantic City especially. So any place where there's legalized gambling.

[Jim Gaffigan]

Yeah.

[Dale]

Puerto Rico, Vegas, and occasionally Dick Clark would throw these like extravaganzas at Madison Square Garden. My dad and 14 other acts doing three songs each. And so that was like from 72 to 75. And then my dad sort of nuanced his way to a nightclub act and that's where I came to play. So, you know, babysitting really wasn't a thing until the late 80s.

[Jim Gaffigan]

Yeah.

[Dale]

Meaning my parents didn't trust any stranger to watch me. So you had to be a part of the act.

[Questlove]

So in order to get into the club.

[Dale]

Well, just to keep an eye on me. So they made up, they made up jobs. So I'll say that around 7 or 8, my dad kind of trained me and my sister like I was a stranger. It was very normal for an 8 year old to come into a nightclub establishment with some measuring tape, ask for a ladder. I pull out a razor blade, cut out light gels, put place light gels.

[Jim Gaffigan]

Yeah, yeah.

[Dale]

Put electric tape down, ring the monitors out. I'd run the sound. I was the richest, like 9, 10 year old ever. I made. I'd make about $120 a week between like 79 to 83. And then one day my dad's drummer got sick. He had a car, motorcycle accident. We were at Radio City. My dad was like, well, you know, the show. And he's elated because he doesn't have to pay a drummer and a band leader like 600.

[Questlove]

But had you spent time on the drums?

[Dale]

I started drumming when I was two.

[Jim Gaffigan]

Okay.

[Dale]

I got a. I got my first set when I was 7. But I didn't know that my entry was going to be Radio City. Radio City Music hall, like leading a full orchestra.

[Jim Gaffigan]

Right.

[Dale]

But he's like, you know the song already, like it's 20 minute show. Good. So I did it and then he. My first gig with him was at Radio City. My last gig with him was at Madison Square Garden. And then the next day I got on a plane and we moved to London.

[Questlove]

You know, it's weird about doo Wop. Like, I think doo Wop had a profound impact on Frank Zappa.

[Dale]

Oh, absolutely.

[Questlove]

I mean it's like, oh, it's all the humor in Zappa.

[Dale]

It's all. Absolutely. Yeah, absolutely. I did see, I even, I thought it was, I thought it was more novel than anything. And then when I was working on my first film, Summer of Soul.

[Jim Gaffigan]

Yeah.

[Dale]

Which at the time, we were calling Black Woodstock.

[Jim Gaffigan]

Yeah.

[Dale]

My first battle research was I watched everything about actual Woodstock before I did my film. And I found out the story was that Shannon came as a recommendation from Jimi Hendrix. I was like, really serious artists like Hendrix, like, he's like, no, man. These guys that do the music just, like, the 50s, like, I couldn't rap that. So once I got him play with.

[Questlove]

The Isley Brothers, so, like, he knows it.

[Dale]

Yeah. But in. In my mind, I think I was looking at my dad and his peers kind of the way that, like, roots kids look at us now, right? Like, I know they're backstage watching, like, man, this ain't NBA young boy. Look at these old rappers on, like.

[Jim Gaffigan]

Yeah, yeah, yeah, sure.

[Dale]

But I didn't realize, like, how heavy nostalgia culture was. And that was the first wave of.

[Questlove]

Nostalgia culture, but also, like, so, like, rock and roll starts, what, 57, 58, depending if you believe it's Bill Haley or Ike Turner.

[Dale]

Right.

[Questlove]

And then it was invented in their lifetime. So whatever came out of that momentum profoundly affected them. So it's like. It's almost like a childhood, you know, it's part of you. It's not even nostalgia, I would think, for Hendrik.

[Dale]

Yeah. Looking in the rearview mirror is everyone's favorite pastime, you know? Yeah.

[Questlove]

But, like, it moves you.

[Dale]

The.

[Questlove]

The music kind of, like, brings back something, I guess, that is nostalgia. But, I mean, like, a lot of Jimmy's stuff, you know, kind of grew up in that. That early R and B stuff, right?

[Dale]

Yes, absolutely. Playing with. Yeah. Matter of fact, the story of him sleeping on the. The Isley Brothers, I guess, discovered him, like, on a park bench, sleeping cafe. What, and heard him play guitar.

[Jim Gaffigan]

Yeah.

[Dale]

And bring him home to Jersey. And then.

[Jim Gaffigan]

Yeah.

[Dale]

He becomes their. Their.

[Questlove]

So that gave you a new respect for your dad.

[Dale]

It did. I mean, at the time when I was doing it, I wasn't looking down at it. I think maybe the first time I had questions, like, my first day of school. My first day of school. Music class are our homework. So what I remember about my first day of school was that this is the week that Stevie Wonder releases songs in the key of life. Like, album releases were, like, an event.

[Jim Gaffigan]

Yeah.

[Dale]

And when this album comes along, it. It almost felt like. I would say it was almost akin to, like, black version of War of the Worlds.

[Jim Gaffigan]

Yeah.

[Dale]

Like, we brought the record. We all sat as a family in front of the stereo and just sat and listened to it from start to finish. And I'd never seen a book I'D never seen liner notes before.

[Jim Gaffigan]

Yeah.

[Dale]

Pictures, some, like, reading the liner notes and everything about what's a harp? What's a. What's this in Clavier? Like, asking my mom, what's this word? And reading, like, all the musicians. And that was our homework. We had to purchase that album, bring it in the next day for further, like, instruction. And I believe the next homework assignment was bringing your favorite 45.

[Jim Gaffigan]

When.

[Questlove]

Where were you going to school then?

[Dale]

This was the private version of the performing arts school in Philadelphia.

[Questlove]

And you bring any favorite 45.

[Dale]

And so I brought in Frankie Lyman and the teenagers why Do Fools Fall in Love?

[Questlove]

That's a good song.

[Dale]

Right? But here's the thing, though. So when I submitted my 45 in my teacher's little perplexed, like, oh, this was a hit when I was a kid, I was like, huh?

[Jim Gaffigan]

Yeah.

[Dale]

I thought all doo wop music was, like, new.

[Jim Gaffigan]

Yeah.

[Dale]

No, my parents were just hiding, like Disco Duck by Rick D's from me, and he was born to be alive. Like, all those disco songs, like, yeah, yeah, yeah. They. They did a great. Actually. I believe my keyboard player now still hasn't broken the news that Michael Jackson is no longer with us to, like, one of his youngest kids.

[Questlove]

Oh, my God.

[Dale]

So it's all, like, I even see my band members, like, and I'm. I'm saying, yo, man, you're going to do him a disservice. Like, this Nas album came out 35 years ago, yo. Like, why he. He brought his kid to a Wu Tang show, and his kid's like, 7 years old. I'm like, dude, you. Are you ever going to tell him the truth that this song is, like, 30 years old? Like, his kids think that the hip hop they're listening to is brand new.

[Questlove]

But that's what got him. So he wants to make sure it gets in there.

[Dale]

Yeah, parents are dirty like that. So, yeah, when I was young, once I got into school, then suddenly someone drew a timeline of, like, this is old music and this is new music. But I was too late. It was too late. Then you missed a Chuck. Yeah. But then also, I became. I pretty much. I'll say that I was lester bangs by 11, and especially because I was reading periodicals like I was reading cream at 10. You know, I was bored at home. There's nothing to do but read all these Billboards and Rolling Stones and stuff. And so, like, I had.

[Questlove]

Because your dad had them.

[Dale]

Yeah. Cause my dad had them.

[Questlove]

Industry magazine.

[Dale]

Yeah, I'd read them, read them all Billboard Cream, Rolling Stone, all those periodicals. Cashbox. And so I'll say that I had an adult's knowledge, or at least adult music snobs knowledge of music by the time I was, like, 12.

[Jim Gaffigan]

Yeah.

[Dale]

And I was trapped. Like, he had successfully raised Doo Up a clone. Yes. A music snob clone. So.

[Questlove]

Well, where does jazz come in, though?

[Dale]

Okay, so I went to private school up until the 10th grade.

[Jim Gaffigan]

Yeah.

[Dale]

11Th grade. I begged my parents, like, I want to go to a real school where kids are playing instruments and acting and.

[Jim Gaffigan]

Yeah.

[Dale]

I wanted to go to the. The public school version.

[Jim Gaffigan]

The.

[Dale]

The Philadelphia version of fame. I wanted to go to that performing arts school.

[Jim Gaffigan]

Yeah.

[Dale]

To be honest with you, there was a girl who danced on a very popular local television show, the same show that Kelly Ripa danced on before she became famous. It was called. What was local. It was called Dancing on Air.

[Jim Gaffigan]

Yeah.

[Dale]

But it got syndicated. Dance Party usa. So it was a popular local dance show. And there were two girls that me and my best friend were into, so we, like, wrote them letters in the summer, like, dear da, da, da, would you go in our junior prom with us? And da da, da, da, whatever. And my girl responded, his didn't. And that was my further motivation to make the sacrificial friendship bomb. And I said, you know what? I'm going to transfer to her school, and then I'm gonna hook you up for your junior prom. But really, I just wanted to go to that school, to go to, you know, private school. He never got hooked up with that girl, but I got into that school, and that's how, like, I went to performing arts. And literally, it was like. It was like Fame. Like, kids were breaking out in the production. Boys to Men were singing in the bathroom, testing the acoustics and all that stuff. And there was a Jets and Sharks or Bloods and Crips version of gangs in my school. And the conservative side was Christian McBride and Joey DeFrancesco. And these guys were like, like, typically, Miles Davis would pull Joey out of school for, like, two months to tour with him. The Marcelluses would use Christian. These guys are, like 15, 16, and already, like, young lions.

[Jim Gaffigan]

Yeah.

[Dale]

So in order to get their respect, I had to learn their language. But then on the left side of things, there was a cat named Kurt Rosenwinkle who is also just. He's on Verve Records, like a genius musician. And he was more Zappa, Captain Beef Barb, Experimental.

[Jim Gaffigan]

Yeah.

[Dale]

So I'm like, serving. I joke that I was. I was on the side of whoever, whatever gang's Winning. Like, Richard Pryor once had that joke. Like, I. I joined two gangs, and whoever was winning, that's the side I was on. So just to fit in, I had to crash course jazz. But on the other side of that, during lunch breaks, the cool kids table were the rap kids, and they were all the ex graffiti artists of Philly that got arrested and had to. You know, when you got arrested for graffiti in Philly, you had to, like, paint walls and do respectable art.

[Jim Gaffigan]

Yeah.

[Dale]

And then maybe one out of eight would be like, wow, you. You have a really good eye for art. Hey, why don't you go to performing art school? So Tariq Schroeder Black thought my partner in the Roots was a graffiti artist that got caught and was a really brilliant, gifted visual artist, and he goes to performing arts school. So all the thug kids are in hip hop. And so when you're looking for what's my table?

[Jim Gaffigan]

Yeah.

[Dale]

In the lunchroom, I was allowed to sit with the cool kids because I was willing to beat the lunch table with spoons and my fists so that they could freestyle for, like, hours at a time.

[Jim Gaffigan]

Yeah.

[Dale]

I didn't have to say nothing as long as I just kept the beat going.

[Jim Gaffigan]

Yeah. Yeah.

[Dale]

They would just rhyme all day. So that's kind of how, you know, that's. That's kind of how the Roots got started. So.

[Questlove]

But you were never a jazz head.

[Dale]

My dad was big into respectability politics. You know, there's always that adults, like, you know, tuck your shirt in and, you know. Right. Stop showing your boxing underwear and, you know, thinks that every rap song you listen to is Suck my dick and. Yeah, whatever. Phil Floor and Filthy. He sort of looked at hip hop that way. And so he wanted me either in classical music or jazz music because that's respectable. Right. And of course, you know, his. His thing is he's thinking about my survival.

[Jim Gaffigan]

Right.

[Questlove]

But as much as you can, when you've agreed to let your son pursue a musician's career and support it, it's. It gets a little tricky to. So given that there's no security in any of it, it To. To find a place for him.

[Dale]

People think I'm joking, but my dad didn't find out about the Roots until our second record.

[Marc Maron]

Was he okay with it by then?

[Dale]

Once? Well, no, it was. It was like. I think my cousins gave me away. They're like, Uncle Lee, you know, our. Our version of the New York Times, which was the Philly Inquirer.

[Jim Gaffigan]

Yeah.

[Dale]

You know, they're. He comes in with like, you Know, I made the front page of the Sunday paper. He's like, so, what is this? And I played it off like, oh, you know, me. Me and Tariq got some project, and I didn't break the news to him that I wasn't going to Juilliard or. Or new school or whatever.

[Jim Gaffigan]

Yeah.

[Dale]

But I'll. I'll say that. And again, his thing was always about safety and survival and a lot of his fear, like, his family did not support his. You know, as much as we talk about, like, conservative movements in America, and I know, like, most people think, like, when you think of the conservative right, you think of, like, whoever's watching Fox News, whatever.

[Jim Gaffigan]

Yeah.

[Dale]

I assure you, no one's more conservative than the black Christian family. And for him, it was just definitely by our fourth album, the Things Fall Apart record. That's when he was like, okay, he's safe. Yeah, number one. It's like, well, here's your keys to your car, and here's your house. Your new house, dad.

[Jim Gaffigan]

Yeah.

[Dale]

You know what I mean? That. But mostly, yeah. Yeah, he just.

[Questlove]

That was one big hit on there.

[Dale]

Well, that's where we won our first Grammy. Like, Geffen, we were probably the last group that had the system of, like, slow rollout and, you know. Yeah, we will. We'll work this slowly. Of course, we wanted success instantly, but it took four albums for us to build, you know, like, our. Our fan base.

[Jim Gaffigan]

Yeah.

[Dale]

And a lot of blood and sweat behind that. But it was the right move. Like, if you ask me now, was it better to take this Tortoise and hare route? I'll say that. Yes, it was. Absolutely.

[Questlove]

Well, you were getting all these other skills.

[Dale]

Yeah, but, I mean, at the time, it was the Tortoise in the Hair. Like, you're watching, you know, the Fugees surpass you on the racetrack, and then you're watching Outkast surpass you on the racetrack, and then you're watching Kanye and everyone else, and you're like, oh, we're just never gonna make it. You know, we're slowly gonna get there. But I will say that we're still actively here, still acknowledged, and literally better than we were when we first started. Most people peek out, you know, every group, it's like, oh, I like the first five outcome.

[Questlove]

Well, it's kind of interesting, though, given your father's sensibility around security, that that must have played into the decision to be the band, you know, when to make the business decision around being this, you know, the. The show band.

[Dale]

Oh, for the Tonight Show.

[Jim Gaffigan]

Yeah.

[Dale]

So, yeah, after 18 years of just 200 gigs a year and right. You know, we. It wasn't joking, you know, Celine Dion had managed to figure out like a residency. Like, we were always like, man, just there ever was a way for us to just make the living we're making now, but just in one place and not having reasonable hours. Well, yeah, like, I'm the only non married member of the group. Because you can't have any sustainable relationship.

[Jim Gaffigan]

Yeah.

[Dale]

You know, you can't have a sustainable relationship and really be an effective member of this life. You know what I mean? And so we, when this opportunity came up, Neil Brennan, co creator of the Chappelle Show.

[Jim Gaffigan]

Yeah, I know.

[Dale]

Neil had said to Jimmy, quote. Jimmy's like, well, what about music? Who, you know, who should I get? And Brennan's quote was, well, ask the Roots, because they know all the great musicians and the best musicians around. And Jimmy just cut it off at the Ellipsis. Yeah, ask the Roots. So he asked us. And I mean, I'll be honest with you, we just got into the mountaintop of really good money. The idea of touring and having maybe five to six figures in your bank account when you get home was a new idea. I didn't think we were gonna take it. And then Jimmy did something miraculous once, which was he came to see us in ucla and I had did some college interview inside my trailer. And 20 minutes later I'm done the interview and I come out my trailer and I see Jimmy and the rest of the Roots. And a kind of an eight is enough. Bring it on. Human pyramid.

[Jim Gaffigan]

Yeah.

[Dale]

And the fact that Black Thought was on the bottom row getting his. His like $2,000 Japanese denim dirty.

[Jim Gaffigan]

Yeah.

[Dale]

I looked, I was like, what did this guy do to disarm the Roots that like. I've never seen someone disarm us in record time. Yeah, they're all smiling and joking and I'm like looking at my manager like, we're not getting rid of this guy no time soon.

[Jim Gaffigan]

Right.

[Dale]

He's just like, nah, I think we're stuck. So we. We definitely weren't going to accept the. The gig. But he just, you know, people ask me all the time, like, is. Is he always like that? Is he always on 100? He is always on. He's. He's the spike in any punch.

[Questlove]

I think he's. I like doing his show more than any of them because he's a great audience and he's like engaged.

[Dale]

We're still, we're still. I feel like we are the talk show of. We're the pop culture offspring that grew up watching Letterman and you know what I mean, that sort of thing. Now we're the generation after. So for me it's still like you would think that we would slightly maybe perhaps like. Yes. Is it new? Like the honeymoon was your first three years? No, everything was exciting and new and.

[Jim Gaffigan]

Sure.

[Dale]

Oh my God, dude. Bruce Springsteen's like right there. Oh my God. Prince destroyed your guitar, dude. Wow. No one caught it when it hit the ground. Like all these things are happening. But Even now, like 16, 17 years later, I still find it like I love coming to 30 Rock.

[Jim Gaffigan]

Yeah.

[Dale]

Yeah. And especially now that I can sneak up to 8h.

[Jim Gaffigan]

Yeah.

[Dale]

And just sit there and watch that whole world like that's. And you mentioned that like just watching how the whole place operates.

[Jim Gaffigan]

Yeah, yeah.

[Dale]

That's the only, like that, you know, most people come, they want to hang in the green room or. But also you like, do all, all this other stuff too. Yeah, I, I take it in. I.

[Questlove]

And you know, your filmmaker, Grammys producing, all of it. And I want to say that, you know, I watched the Sly doc. I. I thought that like, you know, you did an amazing thing to, to sort of, you know, you know, honor and almost establish that guy's legacy publicly. And you know, because I don't, you know, I, I know the songs and I know him, but we more or.

[Dale]

Less know of the. The Right.

[Questlove]

A little bit. But I knew he was great. But you know, for you and the way that you put it together, used him as a portal to sort of like explain the expansion of music through this one guy.

[Dale]

And it's all justified, I think most of the time. And I go through this myself where, you know, oftentimes when people talk about the hard traveled road of successful people, a lot of the times you're expecting a defensive response like the world's tiniest violin. Oh, woe me the richest up. Yeah, right, right. And the thing is, is that in my career, especially with my, my canon, as far as the artists that I'm associated with, as far as many of the acts that, whose records I've been on or produced or drum for, whatever, they kind of have one thing in common, which is a tendency to subconsciously or maybe purposely self sabotage.

[Jim Gaffigan]

Yeah.

[Dale]

And I'm often asked like, well, why is this person like, you know the term, like, you only have one job, like, all you have to do is show up. And why is this person always later? Why is this person. Why is this person dead? Why is this person on drugs. Why is this person always fucking up? Why is this person? And I really, I got tired of answering that question. And I figured this is probably the closest way that I can explain to you what a person feels like if they are a successful unwilling participant. And my main goal was to get all of these artists to sort of be a proxy for Slydet to answer these questions.

[Questlove]

And how'd you frame it? The burden of black genius.

[Dale]

The burden of black genius, yeah. And first of all, one of the hardest things, the one thing that isn't clear in the doc, is the staggering amount of no's that I got from the music community in terms of being a talking. At the end of the day, yes. Getting Andre 3,000 D', Angelo, Nile Rogers, like getting the talking Heads I got was enough. But there's at least 15 other artists that either agreed and stood us up or last minute. Because vulnerability is such a hard, hard thing to be. And I know it. It's one of those easier said than done things. Like if you're on the outside looking in, you're just saying like, wow, I would do anything to spill my guts and show the world my insides and be a goldfish. But you know, for a lot of these artists, there's, there's nothing normal about this level of, of stardom. And Sly was the first. Even though I spoke earlier about the Jackson 5 being the first recipients. Really the reason why Thriller was allowed to happen was because Sly dropped the baton on the Floor in 1974. Michael picks it up in 82 with Thriller. But Sly was the first person that out the gate post civil rights period, that had the freedom to do whatever he wanted. Every creative idea he had was like an establishing role. Everything that he did 50 years ago, we're still using now. The first to use a drum machine, the first to really take advantage of multi track recording. Like the bedroom musician doing everything by himself. He was the pioneer that such an amazing poet like his pen game was out of this world.

[Questlove]

But also the thing you were saying before is that he was the eye of the needle in terms of the history of music up to that point.

[Dale]

Yeah, he was because he was a.

[Questlove]

DJ and because he took it all in and because he had this brain that separated sounds and melded it into his own. That. But it's all sourced. He.

[Dale]

Yeah, he. He started out as the classical prodigy and. And choir church leader by the age of six. Yeah, was by 19 almost to the level of Casey Kasem was like he.

[Questlove]

Was a popular DJ.

[Dale]

Bottom five.

[Jim Gaffigan]

Yeah.

[Dale]

Yeah. And what's weird is that he, in 62, as a radio DJ, will basically raise the counterculture tweens that we will later know as hippies. So all those hippies that you see in, like, the Summer of Love, 67, 68, they're in 1962. They're 12 and 13 listening to Sly on the. In the same way that, like, Robin Williams was in Good Morning Vietnam. That's how Sly is a. He's playing piano on top of Ray Charles and he's making his own commercials up and all those things. Like, that's how his mind work. But, you know, the one thing that a lot of the world is unaware of is that when you are an isolated success, the first thing you feel is guilt that it's happening to you and not anyone else. You know, so it's hard to bask in the glory of comfort when even now, like, I, like, what slide go through. What slide goes through in this doc is kind of like what I went through after the Oscars in 2021. Like, literally just this insane amount of guilt that you feel.

[Questlove]

And what about all the other guys are, you know.

[Dale]

Yeah. When people ask me, like, what did you. What did you feel before the slap happened? You know? Oh, my. Right, my. And they thought. Most people thought I was just like, you know, ducking, commenting on the slap. Like, oh, I really wasn't paying attention.

[Questlove]

But, oh, because you were the Oscar right after Chris got hit.

[Dale]

I know that was my Oscar. Oh, so. And that's the. Let me. Let me tell you how my ex girlfriend said. She said, congratulations, you. You got exactly what you wanted. And I said, what do you mean? She's like, for the last two years, you've been struggling inside your own body to accept this new life that you have. And you made a deal with the universe and you said, man, if there ever was a way for me to quietly win this Oscar and not make anyone uncomfortable with my success, like, what's the quietest way I could win this Oscar and it not bother anyone. And it's like she says that Will Smith, Chris Rock, she's like, you can either manifest your dreams or you can manafuck your dreams. And she's like, you chose to manafuck it, and you got exactly what you wanted. Because sure enough, when the slap happened, everyone stopped watching tv, went to their phones, like, what the hell happened? Came back commercial, and it was almost like I'd never won the Oscar. And so in that entire year, like, I then knew how Sly Stone felt. It was Just a level of guilt. And at one point I wanted to, like, I wanted to. I think I'm the first person that like, prayed that I would get canceled or like, just make the stop. Like, I'm not used to the attention this level. Well, did you feel like, like, okay for you?

[Questlove]

It's been a real slow burn for me, dude.

[Dale]

And I don't think I hit that. Did you imagine that you get to this, this, this level of. Especially because you didn't design this. I had since the age of two, I was raised to be on a stage, meaning my band. I want, I want my success to look like this.

[Jim Gaffigan]

Yeah.

[Dale]

And then like, if someone comes to you and says, like, when I'm busking on south street with my friend with a bucket and drumsticks, if, if some sort of Jacob Marley figure, you know, comes up to me says, hey, okay, so it's 95. Okay. You don't know this yet, but in 27 years you're going to be a. And Oscar award winning film director and documentary maker. And I look at you like, you were crazy. He was like, no, that's not the crazy part. You'll. You'll also be the next Doc Severson and Paul Schaefer. No, I'm not doing that. Like, I'm doing a band with my best friend. And. And so it's, it's hard to, to.

[Questlove]

To own yourself, you know, when, like I feel that now, like, because I'm having a lot of anxiety because so much is going on and you know, I'm not at that level where I'm winning Oscars or anything. But it's uncomfortable for me and I just talked about it for the podcast tomorrow to acknowledge that, you know, I'm doing good and I actually feel good about myself, but it's alien.

[Dale]

Is it hard to feel good in the worst times ever?

[Questlove]

Yes. Well, that's a whole other layer.

[Dale]

So that's the way the universe is working with me, the way that I keep secrets. Like, this is the. Okay, just maybe 20 minutes before I got here.

[Jim Gaffigan]

Yeah.

[Dale]

I got a random call that like, dude, it's your turn. Like, the Simpsons just called you. And I'm like, what? But my whole thing is I gotta keep it a secret. Like, oh, I don't feel. Not that I don't feel comfortable. Yes. I've done enough work in therapy to talk myself off of like many a ledge.

[Jim Gaffigan]

Yeah.

[Dale]

But yeah, I mean, every day I kind of struggle with when something really good happens to me. It's, it's. There's such a gutted feeling. And, yeah, I don't. Don't let no one find out about it.

[Marc Maron]

But what's.

[Questlove]

Have you identified what the source of that is?

[Dale]

I realized. So there was a point where I kind of had. I had a therapeutic breakthrough during the Pandemic, which helped me complete Summer of Soul. But then I thought I was just doing a niche documentary that no one's going to see anyway. So, you know, three months later, and then I'll go back to the Roots album that I've been working on for the last nine years. And then, you know, once Disney starts calling you, like, you realize that you have a chance to get on that stage to accept that award, right? And I'm like, all right, get out of here. Get out. So once those doors open, which I totally wasn't prepared for, I'll say the. Maybe the first four months, there was an anger feeling because I'm like, damn. Since the age of five, I've been prepping. Like, I've studied every album, every engineer, all these liner notes, like, why can't I get success on the terms that. That I want? I want to be a successful musician in a band with my best friend from high school.

[Questlove]

Okay, I know what you're talking about now.

[Dale]

And I'm like, I didn't. I didn't even go to nyu. Like, what the fuck? Yeah, so there was that.

[Questlove]

And then I know that feeling because when I got the podcast and that became successful, I'm like, I'm a comic, right? And people go like, I really like your show. I'm like, my comedy, they're like, oh, you do comedy?

[Dale]

And it's like, God damn it. I went to see the weekend at MetLife Stadium in New York. And, you know, his audience is Jen Alpha. Jim.

[Jim Gaffigan]

Yeah, yeah.

[Dale]

You know, a bunch of kids born in 2003 or whatever. And these kids walk up to me, it's like, yo, you were the guy in the SNL bit with. With Pete. With. With Pete and Timothy Chalamet, right? And I was like, yeah, I was. I. I did that, too.

[Jim Gaffigan]

Yeah, yeah.

[Dale]

They're like, cool. And then they just walk away. And so sometimes I do feel like someone joked, I think Chappelle told me is like, amir is. Sometimes being me is sort of like people only recognizing Michael Jordan for the Hanes commercials.

[Jim Gaffigan]

Right.

[Dale]

And nothing else.

[Jim Gaffigan]

Right?

[Dale]

So, yeah, there was. There was one time where I got a lap dance. I was at a bachelor party in Vegas for friend. I was getting married. And so girl walks up to me, starts Crying. And I was like, what happened? She's like, you just don't know. Like, I grew up as a latchkey kid. And I'm like, where's this going, lady? Where's this going? And she's like, you know, 27. She's like, but, man, that song that you guys did on Yo Gabba Gabba. Oh, that came out when I was 12 years old. And when I seen you, I just started crying because it made me miss my grandma. We used to always sing that song. And I'm like, jack Fleet. You know what I mean? Like, that's what I'm known for. So now just stop fighting it.

[Questlove]

Well, I think it's hard to acknowledge that it's all you. It's all you. Because, like, even if with the Sly Doc, is that you found a way to channel all of your, you know, not just historical wisdom, but musically historical wisdom, and also, you know, confront the question of the burden of black genius, which most of the guys didn't really know how to frame or what you.

[Marc Maron]

Were trying to say.

[Dale]

Right.

[Questlove]

But then, you know, the arc of Sly's career, you know, there. And there's also that other thing where, you know, once you appeal to all these white audiences, and then, you know, you have to deal with that guilt of selling out or tomming or whatever.

[Dale]

Yes, yes.

[Questlove]

So then, you know, you gotta. And then he comes back around, redelivers himself to the black community, and still holds on to all of it. But I thought it was a way for you to channel all the questions about yourself and also to really place.

[Marc Maron]

You know, the impact of a very.

[Questlove]

Specific guy who was fundamentally a black musician on the entire fucking world of music. But I think that in looking at yourself, that the only way that I accept it is like, you know what? I am pretty good at this other stuff.

[Dale]

My mom, when my mom first seen it, she said, I see what you did there. She's like, you told Sly story to tell your story.

[Jim Gaffigan]

Yeah.

[Dale]

And I was like, busted. So, yeah, I used a story to tell my story because, you know, I figured we might as well show the first domino falling. And so it was hard, though I will say that unlike Summer of Soul, extracting that much pain out of people and telling those stories, it. There's a lot of. I didn't realize. Okay. So when I used to watch the Sopranos, there's a moment where Dr. Melfi has to talk to her therapist.

[Jim Gaffigan]

Yeah.

[Dale]

And I didn't realize, like, how meta it was. Like, oh, damn. Even she has to have a therapist. To get rid of all the baggage that she takes on from her clients. It was one of those episodes where, like, Tony may or may not have just admitted that he had to handle a situation and the stress that she. But that's how I felt. Like there was one point where I got a second therapist just because the, like, getting a second therapist and subsequently working on SNL was almost like my joy. Space of trying to wash the sadness of the three year Sly period where you, you. It's almost like you take on.

[Jim Gaffigan]

Yeah, yeah, yeah.

[Dale]

All the pain that he went through just to tell his story. And so, yeah, it's, it's, it's not for the faint of heart, but, you.

[Questlove]

Know, beautiful work though.

[Dale]

Thank you.

[Questlove]

I mean, like, you know, it's like one of those things where I'm like, thank you, you know, for planting this guy's flag and then for planting your own flag and for giving me a new understanding of, you know, a fundamental of modern music. I mean, like, it's all there. But, you know, you do that with music too. I mean, that's the one thing about, like, I'm not a huge hip hop guy, but the integration of the textures of all music preceding you, I mean, everything is some sort of mashup of the history of how we got here musically.

[Dale]

Well, yeah, I mean, literally, hip hop is Warhol's version of taking everything that's before you and. And recontextualizing.

[Jim Gaffigan]

Yeah.

[Dale]

You know, and that to me, you know, oftentimes, I mean, people my age now are the establishment, so it's easier to convince them. But, you know, the, the generation before, you know, when you're trying to convince, like, Led Zeppelin's lawyers that one snare drum sound, you know, from Physical graffiti shouldn't equate 100, you know, percent publishing, especially in light of like, wait, didn't you guys steal this from this blues artist? Like, the irony of you calling this out for stealing. But it's just, I think all art is derivative, of course. Everything's just remixed and redone again. But I've also learned how to be a suit. So that's the smart thing, like, and that's the thing I feel guilty of. When, before Bismarck, he passed away, one of his last words to me is like, damn, quest, when did you become a suit? And we were joking, but when I went home that night, I was like, ouch, Biz Markey. Like, yeah, but also a suit.

[Questlove]

No, but it's in service of maintaining your, you know, the ability to manage your talent, to use it in different places. At some point you have to delegate. At some point you have to manage, you know, the situation so you can execute how you want to execute. And when you have a lot of things that you do, you got to be a suit sometimes.

[Dale]

Yeah. But, you know, sometimes it makes me feel like I'm not an artist or I might not be seen as an artist.

[Questlove]

Well, that's crazy.

[Dale]

You know, that's it.

[Questlove]

Well, that's a voice in your head that you somehow nurture and keep just to keep you in check.

[Dale]

Do you feel like an artist now? Like you're so responsible and you've done such a service in terms of conversation and communication. Dude, I listened to that Robin Williams podcast at least five times a year. Yeah, I'm, I'm actually working on a project right now that is kind of close to the storyline of awakenings. And I think every person on this, I've played them. The infamous Yo, Bobby D. Like the, the Robin Williams story of. Yeah, yeah, Bobby D. Breaking character.

[Jim Gaffigan]

Yeah, yeah.

[Dale]

Like, that's my all time favorite story. But even for you, like, do you feel closer to Lenny Bruce or, or Carlin? Or are you look the next Lauren Michaels?

[Questlove]

Well, no, I don't have a business sense, so, like, I'm, I'm definitely you.

[Dale]

Do you believe it?

[Questlove]

Yeah, well, I'm not a producer, you know, I still work in the zone of, of immediacy.

[Dale]

But if thrown into the river, would you learn pretty damn quick?

[Questlove]

I don't think so. And the thing, but I understand what you're saying, like, because, you know, I'm now on this Apple show, which is a cute show and families love it, and it makes me feel feel good.

[Marc Maron]

You know, I've gotten to a place.

[Questlove]

Where I'm like, well, these people seem to really enjoy this.

[Dale]

Right.

[Questlove]

And that's necessary. And the podcast brings people, you know, an intimacy with, with talented people that ranges the full spectrum of experience. And then I do this special that's coming out Friday that, you know, is the best comedy I can do. And it's right up there, you know, with, you know, saying what I need to say and how I want to say it. And, you know, there's just different parts of me that seem at odds with each other. And sometimes I wonder. It's like, oh, my God, all these people that like the bag guys movie or like, stick, they're going to watch the comedy and they're going to be, holy shit, who is this guy? And it's like, fine, I, I, I.

[Dale]

I have multitudes Is there an itch that you still want to scratch?

[Marc Maron]

Not really.

[Dale]

Are you. You're satisfied?

[Questlove]

I'm satisfied in the terms of, like, my. This output that I've done. You know, the podcast, you know, as a body of work I'm. I'm proud of, you know, even as we head out of it, the comedy. I've never been better. So I've let go of this idea that I have to be singular. And it's helpful that, you know, this idea of integrity or selling out or whatever.

[Marc Maron]

I never sold out because no one.

[Questlove]

Was really offering me that much money, if any. So I've always been able to do it the way I want to do it, and I'm doing most of what I'm doing at a pretty good level, and they are all parts of what I wanted to do, but they do seem separate sometimes.

[Dale]

So there is a satisfaction destination.

[Questlove]

It's slightly. It's just starting to happen. Don't ruin it.

[Dale]

It's important for me to know this because, you know, right now I am pivoting to scripted.

[Jim Gaffigan]

Yeah.

[Dale]

I'm pivoting to production. I am going to attempt to scratch the itch that is, you know, does a world Want a 17th roots album? Like, nothing scares me more when I go to concerts. Like, and now, you know, here's the song from the new album. You know what I mean? That's when, like, all right, let me go.

[Jim Gaffigan]

Yeah, yeah, yeah.

[Dale]

To the bathroom or get some popcorn. But I. There's still a musical itch that I still. I don't know, it's like getting a bunch of. Of. Of. Of walks and singles and. Sure, maybe a double. And it's just like one grand slam. Like, that's. But I also know that I'm insatiable by nature. And.

[Questlove]

You know, I. I think, you know, you'll do the music if you want to do the music. You just got to kind of temper your expectations if you're going to put that out there and not beat yourself up about it. And this other stuff is new and exciting stuff.

[Dale]

Are you in the space where, if you want to stop, you could.

[Questlove]

No, I don't know that I can stop. I do fantasize about it. But I do know that I can only do what comes to me in an organic way. I don't put stuff on the docket that I can't handle. But I do find, like, I've been playing a little music publicly, and I find that, you know, you get to a certain age where when things are new, they're Scary, and you want to be good at them immediately and, but, you know, once you start to get a groove going, you're like, well, this is as creative as anything else I've done, and this is, you know, a new place for me, and I'm putting my heart into it, and I have a certain amount of control over it. So what am I going to beat myself up for? For not doing the other thing at whatever level.

[Dale]

Wisdom. Okay. Yeah, I could take that.

[Questlove]

Well, it's good to talk to you, buddy.

[Dale]

Well, I want to thank you for, you know, this, this, this podcast is, has definitely been a lighthouse for me and the way that I've, I've just taken in every episode and, and, and learn from you. I, I, I thank you for this. This is definitely a destination that I've been dreaming about. So now, now I feel like I made it.

[Questlove]

I'm so, I'm so, I'm so glad we got it in, man.

[Dale]

Thank you, man.

[Questlove]

Thank you.

[Marc Maron]

So good.

[Dale]

All right.

[Marc Maron]

There you go, man. It weighs heavy on all of us. Just, you know, who are we? Do we deserve it?

[Questlove]

You know?

[Marc Maron]

Again, he's nominated for three Emmys, including best documentary for Sly Lives. I highly recommend that. Hang out for a minute, folks. Hey, folks. On Thursday, we'll play the live conversation I had with Jim gaffigan at the 92nd Street Y in New York, right after we screened my HBO special for the live audience.

[Bowen Yang]

What does 25, 35, 45 year old Marc Maron think of? A couple things. The success you've achieved, whether it be the podcast, the acting career, you know, the, you know, the, you mean the.

[Marc Maron]

Stuff that happened to you at 40?

[Dale]

No, no.

[Bowen Yang]

But what does, do you sometimes look back at?

[Dale]

Like.

[Bowen Yang]

What does, you know? But you and I also, we connected on this anger thing. Like, people probably don't know, but I.

[Marc Maron]

Was just like, just a simmering cauldron of rage when he was younger.

[Bowen Yang]

Very frustrated. And so, but some of it is.

[Questlove]

But like, I was always like. And I was just sort of like.

[Marc Maron]

That guy's gonna bust.

[Bowen Yang]

And I was just, I just was the guy that, like, he's gonna murder someone. And I did, but I wasn't caught.

[Marc Maron]

No. That's Thursday's episode of wtf. To get every episode of WTF ad free, sign up for wtf. Just go to the link in the episode description or go to wtfpod.com and click on WTF Plus. And a reminder before we go, this podcast is hosted by Acast.

[Dale]

Umrah Lives.

[Marc Maron]

Monkey, and La Fonda Cat angels everywhere.