Questlove: The Art of Self-Sabotage

Summary

Mike Birbiglia's Working It Out

Episode: Questlove – The Art of Self-Sabotage

Original Air Date: October 6, 2025
Guest: Questlove (Amir Thompson)
Host: Mike Birbiglia

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Episode Overview

This episode of "Working It Out" features an inspiring, candid conversation between Mike Birbiglia and Questlove, spanning creativity, self-sabotage, music, documentary filmmaking, and personal journeys through fame and self-acceptance. The discussion revolves around how creatives grapple with vulnerability, rejection, and the fear of success, using Questlove’s own life and projects—especially his acclaimed documentaries and musical career—as the lens.

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Key Discussion Points & Insights

1. Mistakes and the Creative Process

• Music vs. Comedy & Mistakes:
  • Questlove distinguishes the musician’s relationship to mistakes from that of comedians. For musicians, performing every note perfectly signals something is wrong—unlike in comedy, where the "mistake" can become part of the act.

    “People say something's wrong when I play it right. Like the Roots guys know I'm mad when I play everything correct.” — Questlove [02:14]

• The conversation ties into Questlove’s SNL documentary, emphasizing how rhythm and timing unite music and comedy [02:33].

2. Self-Sabotage and Fear of Success

• Relating to ‘Don’t Think Twice’ and Questlove’s Docs:
  • Questlove shares that Mike’s film made him rethink how artists self-sabotage, sometimes unconsciously, out of a desire for control and fear of the unknown.

    “I believe that most people self sabotage, you know, because we want to control. We want to know what's next.” — Questlove [05:46]

• Success as a Source of Anxiety:
  • Both host and guest discuss how success can feel as frightening as failure—Questlove admits to times he’s rooted against his own success.

    "Declines are familiar. Letdowns are familiar, disappointments are familiar...even success is scary." — Questlove [06:28]

3. Making 'Sly Lives' and Dealing with Artists

• Getting Honest Contributions from Artists:
  • Questlove describes the challenge of getting high-profile musicians (like D’Angelo and André 3000) to open up about vulnerability and self-defeating behaviors [08:01].

    “There was 19 other artists that flat out said no or said yes. And seven hours later you’re on set like, are you coming or not?” — Questlove [08:35]

• Sly Stone’s Influence and DJ Culture:
  • The episode dives into how Sly Stone shaped Bay Area youth culture and counter-culture as a DJ, paralleling Questlove’s eclectic, boundary-crossing style [13:12].

    "Sly is an open format DJ...that was sort of unheard of, mixing rock and soul on the same radio station." — Questlove [14:40]

4. Quests for Authenticity and Record-Collecting

• Roots of Questlove’s Musical Exploration:
  • Growing up in a musical family, digging through both hit songs and “flops” shaped Questlove’s comprehensive, unpredictable sets.

    “So I'm probably the first music expert that gravitated towards the flop song.” — Questlove [21:10]

• He describes being thrust into professional music as a child, learning from his father’s nightclub band [18:51].

5. Crafting Iconic Documentary Moments

• Editing and Curating for SNL Doc:
  • Questlove recounts spending 11 months to assemble a seamless musical montage for his SNL doc, using deep musical theory and serendipitous lyrical links for transitions [23:40].

    “Whenever I hear a song, the first thing I say to myself is, what key is this in? How many BPMs?” — Questlove [23:53]

6. The 2022 Oscars 'Slap' and Processing Fame

• Oscars Night and the Slap:
  • Questlove reflects on the surreal experience of winning an Oscar right after the infamous "slap," including his own nervousness about winning and dread of being in the spotlight [29:10–34:16].

    “I was just sitting there, like, frozen, totally channeling out what was happening...I just went back to, oh, God, it's all gonna be different.” — Questlove [32:18]

  • He humorously notes his ex saying he got his “manifuckwish”—the "quietest" Oscar win ever due to the chaos overshadowing it [35:16].

7. Navigating Jealousy and the Tortoise-and-Hare Journey

• On Jealousy and Career Comparison:
  • Both discuss envy experienced towards peer artists’ sudden success, the pain of being only “prestige” instead of “hitmakers.”

    “Inside my voice I'm like, I do care about that shit.” — Questlove on being seen as not caring about hit status [42:59]

  • Questlove recalls feeling Fugees- and Outkast-envy in the Roots' early days, only to realize, years later, the slow, steady journey is more rewarding [44:05–45:35].

    “This was absolutely, positively the best storybook ending ever.” — Questlove [44:20]

8. Turning Points: Embracing Leadership and Vulnerability

• From Second Banana to Center Stage:
  • Questlove unpacks his longstanding pattern of hiding behind collaborators or instruments and how teaching at NYU forced him out of his comfort zone [53:15].

    “I realized there's a level of leadership vulnerability that I've been avoiding by hiding in plain sight.” — Questlove [54:16]

• Accepting and Challenging Himself:
  • He describes his everyday battle to show up fully, engage directly, and not shrink from leadership or self-promotion [54:52–55:34].

9. Simple, Lasting Advice

• The Power of Showing Up:
  • Questlove attributes much of his success to simply continuing to show up, even when he isn’t the first choice or doesn’t have the most accolades.

    “A lot of things I just show up for is because someone else didn't show up for it... you just have to show up.” — Questlove [56:18]

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Notable Quotes & Memorable Moments

• On Self-Sabotage:
  “I’m probably the first person that would actually actively root against something good happening to him.” — Questlove [06:35]

• On DJing and Connecting Eras/Genres:
  “In my mind, my thing is, how am I gonna connect Benny Goodman and Kendrick Lamar.” — Questlove [13:25]

• On the Roots’ status:
  “We were critically acclaimed. But critically acclaimed doesn't necessarily mean that we're hit makers...” — Questlove [42:20]

• On Career Longevity:
  “Would you rather your second album sell 12 million units and... crash and burn... Or would you rather tortoise and hare your way... and not realize that you’ve made it?” — Questlove [44:20]

• On Self-Acceptance and Showing Up:
  “I know I’m the fifth person or the sixth person, but you just have to show up.” — Questlove [56:18]

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Key Timestamps

• 02:14: The difference between mistakes in comedy vs. music
• 05:46: Self-sabotage as an artist's coping mechanism
• 08:01: Challenges of eliciting real vulnerability from documentary subjects
• 14:40: Sly Stone’s boundary-breaking DJ approach
• 18:51: Questlove’s childhood in professional music environments
• 23:40: Editing the SNL opening musical montage
• 32:18–35:16: Questlove describes his Oscars experience post-"slap"
• 42:59: Admitting desire for mainstream success (not just critical acclaim)
• 44:05–45:35: Reflection on the value of a slow-burning, enduring career
• 53:15–54:52: The shift to embracing personal vulnerability and leadership
• 56:18: Sage advice: the importance of consistently showing up
• 57:56: Spotlight on Food and Finance High School, Questlove’s nonprofit of choice

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Resource Links

• Questlove’s SNL and Sly documentaries: Peacock & Hulu/Disney+
• Food and Finance High School: (link to be included in show notes)

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Final Thoughts

This episode stands out as a deep-dive into the emotional and psychological lives of high-achieving creatives. Questlove’s candidness about insecurity, standing in one’s own way, and eventually learning to embrace vulnerability offers lessons not just for artists but for anyone striving for authentic success. The laughter and rapport with Mike Birbiglia, combined with honest stories of anxiety, competition, and fulfillment, make this conversation both grounding and inspirational.

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Transcript

[Mike Birbiglia]

Who are you jealous of?

[Questlove]

Oh, God. Do I have to give a proper noun? I don't know. Do I have the.

[Mike Birbiglia]

The follow up question is who are you jealous of? That you you thought of, but you didn't say. That is the voice of the great Amir Thompson, AKA Questlove, one of my all time favorite episodes. We are re airing this from April. It's a great conversation about creativity. I found it super inspiring and so did our listeners, which is why we are re airing it today in case people missed it the first time or want to recommend it to friends. You can see Questlove in Spinal Tap 2, which is in theaters now. What a sentence. He has had an amazing year. He was nominated for an Emmy for his documentary Sly Lives. He was nominated for the SNL music documentary, which is unbelievably good. I mean, actually the Sly one is unbelievably good too. I mean, these are great, great pieces to watch. So a lot of stuff. If you haven't caught up on Questlove stuff, watch all of that. This week, special announcement. We have launched Working It Out Premium. This is an ad free version of the podcast, which is always available. Almost 190 episodes available, Apple Podcasts. And when you subscribe to Working It Out Premium, you get three things. You get an ad free version of the podcast, no ads. You support the show, which means a lot to us. And number three, bonus content. This week we are releasing our first ever bonus content episode where I tag people's jokes. People sent in their jokes last week on Instagram. They send voice memos. It's really, it's really funny. Some of them are really, really, really good jokes. But we have a great talk with Questlove today. Massive fan of Questlove. We talk about his music, his documentaries, about SNL and Slystone. Enjoy my conversation with the great Questlove.

[Questlove]

I think with comedy, you don't have the same relationship with mistakes that musicians do.

[Mike Birbiglia]

Yeah.

[Questlove]

Whereas, you know, playing like an amateur playing. People say something wrong when I play it right. Like they're roots guys know I'm mad when I play everything correct.

[Mike Birbiglia]

That's great.

[Questlove]

Like, oh, what's wrong with you?

[Mike Birbiglia]

Right.

[Questlove]

I'm cool. Headache, you know, like that sort of thing.

[Mike Birbiglia]

So anyway, that's great that it's funny. Cause in the SNL documentary that you made, it's like, it was one of the best explanations of the relationship between music and comedy I've ever seen that. It's like the rhythm, the cadence, the timing, all those things are crucial. And people Say music and comedy, there's an interrelationship all the time. But you nailed it.

[Questlove]

I learned that it all came together probably in the first year of. And I never say, like, my life on Fallon or the Tonight show or whatever. Like, I consider where I go. Like I'm in my senior college year of 30 Rock University.

[Mike Birbiglia]

Right.

[Questlove]

And you know, and I absolutely believe BU Page intern or Lauren himself in all spots in between, there's like, if you don't go there, if you don't walk away at least knowing four things that you didn't know before, then you're kind of doing it wrong.

[Mike Birbiglia]

So being in the building, you think, was that first created, the first epiphany about that?

[Questlove]

That was the first green light I had.

[Mike Birbiglia]

Wow.

[Questlove]

And this all ties in together because even with us really connecting, me watching Don't Think Twice, and just the entire relationship with rejection and self sabotage, like that played a big role in the Sly Lives doc.

[Mike Birbiglia]

Yeah.

[Questlove]

But you were the first to show it to me in a way that. And I still believe when we had a conversation about it, you weren't too certain if self sabotage was a play in it. You. Okay. So to give everyone context.

[Mike Birbiglia]

Yeah.

[Questlove]

When you did my podcast. God, like 10 years ago.

[Mike Birbiglia]

Yeah, that's right.

[Questlove]

This is a slow turnaround, like 10.

[Mike Birbiglia]

Years, 10 years later. That's right.

[Questlove]

Right. So when you. My theory was that when I saw. When I saw the film, I told everyone who was like, inching 30, whatever, like, this is a must watch. Like, if you want to know what the direction of your life is. Because, you know, you just mess around when you're of college age or whatever. And then I guess you start to think, seriously, maybe 26, 27.

[Mike Birbiglia]

Yeah.

[Questlove]

But once you get to 31, that's almost like when your first midlife crisis comes in because you don't know if you're not doing exactly what you're on the path to doing. Like, you're still like hanging out, messing around at 33, 34. And then suddenly you start to panic. So I told everyone to watch that film. And my assessment was, at least for a couple of the characters, that they weren't aware that they were self sabotaging.

[Mike Birbiglia]

That's right at large.

[Questlove]

So that's where we disagreed. Because you told me that you felt that they were fully aware that they knew what their limitations were and that they were comfortable.

[Mike Birbiglia]

This is where we disagreed about my movie.

[Questlove]

Right. Because. Because the thing is, is that I believe that most people self sabotage, you know, because we want to Control. We want to know what's next. You want to know what the next step is.

[Mike Birbiglia]

Right.

[Questlove]

Solid ground or is this, you know, quicksand? And not having the. The comfort of the know how of knowing if you're going to drown or not.

[Mike Birbiglia]

Yeah.

[Questlove]

Makes people just say, okay, no, no, this is where I get off. This is where I'm stay. This is my life.

[Mike Birbiglia]

So in other words, they're controlling their own kind of decline because they're afraid that maybe the incline isn't there.

[Questlove]

Yeah, I mean, declines are familiar. Letdowns are familiar, Disappointments are familiar.

[Mike Birbiglia]

Yes.

[Questlove]

As opposed to success.

[Mike Birbiglia]

That's right.

[Questlove]

Like, even success is scary. Like, I can tell you firsthand that I'm probably the first person that would actually actively root against something good happening to him. Like, I went through that period of like, literally, like, I can't take it anymore, like, make it stop, like that sort of thing.

[Mike Birbiglia]

So this was a. So in your documentary, Sighing the Family Stone Documentary S lives, the person who I think is in some ways the hero in addition to the director is Andre 3000. Because he says this thing that is so deep, which is. He's essentially describing what you're saying, which is, like, when you're at the level of success that Sly in the Family Stone was at, you're giving to the world and taking from the world so much that when you stop, when one of those things stops, you actually don't know where to put that energy or where to get it from.

[Questlove]

With Andre making that realization in the film, first of all, he was probably the one interview subject that was totally aboard and absolutely down for what I wanted to achieve.

[Mike Birbiglia]

Oh, interesting.

[Questlove]

I kind of had to Jedi mind trick people. We had the Jedi mind trick.

[Mike Birbiglia]

The life of a documentary filmmaker. You have to semi trick people into making what you want to make.

[Questlove]

You can't exactly just come out and say, hey, you know, like how there's similarities between this person I'm doing a doc on and your current life right now. Like your tendency to, you know, not show up at all, or your tendency to keep people waiting for 12 hours, or your tendency to wait decades between records, or your tendency.

[Mike Birbiglia]

So you interviewed some people like d' Angelo and others who have similar self defeating tendencies.

[Questlove]

Yeah. I joke that there's the exact moment where d' Angelo recognizes he's not there to talk about, like, harmony, structure, and like, he takes a drag of a cigarette and I know that stare that when he gives me that stare, like, yeah, yeah, yeah. I knew this was a trap. I knew this was a trap. But I, you know, I had to. It was a very slow walk of trust. But, you know, there was 19 other artists that flat out said no or said yes. And seven hours later you're on set like, are you. You coming or not?

[Mike Birbiglia]

And how many people didn't show up?

[Questlove]

We got stood up maybe three times.

[Mike Birbiglia]

Oh, that's not bad.

[Questlove]

But, yeah, there. There were. I will say that Andre was probably. When I asked him, he was just like, elated, like, oh, finally I have. I have an outlet to let you guys know what I've been going through for the last 25 years.

[Mike Birbiglia]

That's really interesting. So. Yeah, yeah. So with Sly.

[Questlove]

Mm.

[Mike Birbiglia]

Do you know if he's seen it?

[Questlove]

Yeah, he's.

[Mike Birbiglia]

He's seen it.

[Questlove]

Absolutely.

[Mike Birbiglia]

Do you know if he likes it?

[Questlove]

Yeah, he. He likes it. I know traditionally, especially with documentaries, the subject is not supposed to be the executive producer, right. Or have say in it.

[Mike Birbiglia]

Yeah, yeah, yeah.

[Questlove]

But it's kind of weird because in this specific case with the music copyright and all those things, you know, the. The Jackson estate owns the Sly songs. Oh, they do. So 1984. 1984. No, no, it was the smartest business move Michael Jackson ever made.

[Mike Birbiglia]

No, he bought up a bunch of stuff, right? A bunch of Beatles stuff.

[Questlove]

So ATV Publishing was a publishing house. Weird enough, McCartney told him, like, you know, Jackson's like, okay, so what do you do with your money? Like, how do you grow it and all these things? And McCartney says, publishing, buy publishing.

[Mike Birbiglia]

That's crazy.

[Questlove]

But, you know, you're supposed to buy, like, some songs. Mike's just like, oh, I'll buy the entire house.

[Mike Birbiglia]

Right?

[Questlove]

Yeah.

[Mike Birbiglia]

So Beatles.

[Questlove]

Yeah. In 85 stone, 83, he purchased ATV publishing, which is one of the biggest publishing houses. Like, it's Chuck Berry songs, Sly Songs, the Beatles songs, Little Richard songs. Da da da da. And, you know, just in general, they, you know, they tell you from the gate that, you know, if you're doing any project on one of the artists in art that we hold copyright on, the first thing we're gonna do is go to them to see if, you know, if this is something they approve of or they like of or whatever. So, yeah, so he had to give a thumbs up in order for the music to be cleared. But, you know, we kind of came in at the top clear with what our intention was, which is basically to show people kind of what artists go through, but in a way that it didn't feel like, know the world's tiniest violin. So for me, it was important to show it in a way that didn't reek of all. Poor baby. But really just, like, explain to you what, the level of vulnerability that it takes to be that person. Do you.

[Mike Birbiglia]

I mean, your. Your personal story is not that dissimilar from Sly in the sense that you're both musicians, you're both DJs.

[Questlove]

Yes.

[Mike Birbiglia]

I mean, to give. If people haven't seen the documentary, and they should, it's incredible. It's like, Sly was a Bay Area dj, you know, that's a radio dj.

[Questlove]

That's the one thing, when people ask me what's the one thing that I learned about this that I didn't know. I knew he was a dj, but I didn't realize the impact of that d of him DJing. First of all, he starts DJing in 1961 in the Bay Area. He's an open format DJ, which is the kind of DJing I do right when I go to a gig. I don't know if you. Have you been to a party where I've DJed before?

[Mike Birbiglia]

Yeah.

[Questlove]

Okay. So in my mind, my thing is, how am I gonna connect Benny Goodman and Kendrick Lamar.

[Mike Birbiglia]

Exactly. And by the way, if people haven't seen this, they should watch your masterclass on DJing.

[Questlove]

I totally forgot I had.

[Mike Birbiglia]

I mean, it is. It opened my mind to even the art of what DJing is. Like, I didn't understand it before that. That documentary.

[Questlove]

Yeah. Movies and television, really, that's the one thing that irks me about how things are depicted. Because when I'm DJing, I mean, it's the equivalent of me just coming up to you mid set to say, excuse me, excuse me, excuse me. Hey, could tell the chicken cross the road joke? Can you do that one? Can you tell the chicken cross the road joke?

[Mike Birbiglia]

Yeah, yeah.

[Questlove]

Like, you're like, right to get to the punchline and someone interrupts you, like, hey, you know, I think I was suggesting better than you, but they always do that on television. Like, the person comes up to the dj, like, hey, could you pull it in?

[Mike Birbiglia]

Yeah.

[Questlove]

So, yeah, basically, Sly is an open format dj, which means that here he's going to play the Beatles and Bob Dylan, but he's also gonna play, like, you know, the Temptations and even, like, Dyke and the Blazers, Funky Broadway, you.

[Mike Birbiglia]

Know what I mean?

[Questlove]

Like, and that was sort of unheard of, like, mixing rock and soul on the same radio station. Like, that's not supposed to happen. So, yeah, what you're not supposed to do, he's so, you know, he's probably just as a human contrary to start with. Whatever he's not supposed to do, you're doing.

[Mike Birbiglia]

Yeah.

[Questlove]

So I believe that. And on top of that, as a personality, if you're familiar with like Robin Williams character in Good Morning Vietnam, like those morning show Zoo DJs. 91, you know, think about how like Robin Williams acts like 12 characters. Everyone's. Yeah, man, man, like that was Sly. He would. He would make his own commercials up for products that don't exist. Yeah. Or you know, like, let me do a commercial for Tidy bowl. Like.

[Mike Birbiglia]

Right.

[Questlove]

And literally he would make his own commercial. So even then, what. What will happen is those 9, 10, 11, 12, 13 year olds in 1960 will now be the counterculture hippies in 67, 68, 69. So kind of the what you know, as the Bay Area hippie or the counterculture person, like, Sly had a major hand in raising them.

[Mike Birbiglia]

Yeah.

[Questlove]

And so I don't think that part's even known. And even more than that, like with the bands, like the first producer of the Grateful Dead, Sly Stone. The first producer of Jefferson Airplane, Sly Stone. Like, yeah, he also.

[Mike Birbiglia]

I couldn't believe it when I saw that he produced Somebody to Love.

[Questlove]

Yes.

[Mike Birbiglia]

I was like, what?

[Questlove]

Yeah, so basically one of the biggest.

[Mike Birbiglia]

Rock hits of all time.

[Questlove]

Yeah. So, you know, he just. That I didn't realize how much prep work he did five years before he officially came out as Sly and the Family Stone.

[Mike Birbiglia]

Yeah.

[Questlove]

And so, yeah, it would seem rather up his alley.

[Mike Birbiglia]

You know, it was funny because when I did the Old man in the Pool at Lincoln Center, I had just seen your masterclass on DJing and I was like, oh my God, it would be such a dream if Questlove would be open to doing a pre show set.

[Questlove]

And you.

[Mike Birbiglia]

And I asked you, and you were so generous and you did it. What was amazing about the experience was seeing how many of the songs. Cause you sent it as like a 45 minute file. How many?

[Questlove]

Oh, you thought I was just going to feed you songs on your Spotify?

[Mike Birbiglia]

Yeah, yeah. I'm thinking even that I could look up the songs. A lot of the songs, a lot of the songs, they don't even exist on Apple Music or Spotify. So I'm like, what is your catalog? Where is your catalog when you're making that? I mean, it was like, in other words, it was things as different as something from Motown and then the Cure, and then you would find how to match those two things. And then it would be a hip hop track and it would be a Classical track, it would be a jazz track. And where. Okay, where do those exist when you make those mixes?

[Questlove]

So right about now, so I'm in a weird. I'm in the third phase of record collecting. So I've been binge shopping with my dad. The kind of connecting thing that I have with my father because he too was a musician that was a nightclub artist that required songs to learn for whatever environment that he's in. Oh, we gotta learn Celebrations by Cole in the gang.

[Mike Birbiglia]

So since for real, like, that was his job.

[Questlove]

Well, yeah. So my dad was an oldies doo wop singer in the 50s on chess records. Like back in the 50s.

[Mike Birbiglia]

Wow.

[Questlove]

By the time I was born, the first wave of nostalgia culture kicks in. But also my parents did not believe in babysitting. Okay. So you had to be on the job always, so literally. And it was normal.

[Mike Birbiglia]

So you were thrust into like professional music when you were a kid.

[Questlove]

Yeah. So it was. And I would ask them all the time, like, was it normal for a five year old to be in a nightclub? Or when you hear like Brooke Shields tells stories of like. Yeah, I was at Studio 54 when I was 12 and 13. Scandal Culture or, or outrage culture didn't really kick it until like the late 80s.

[Mike Birbiglia]

Yeah.

[Questlove]

You know, with like doing the Jim and Tammy Faye Baker, like the, you know, the clutching of the pearls, outrage. But no one cared.

[Mike Birbiglia]

So.

[Questlove]

Yeah, I was, I was a 5, 6, 7, 8, 9, 10 year old either playing percussion on stage with my family by the time I was 11, I could run the lights.

[Mike Birbiglia]

Unbelievable.

[Questlove]

My sister and I would run the soundboard and the lights as, you know, as kids. So the whole point is that my dad sort of stayed in that circuit for maybe like three to four years between like 72 to 76, maybe.

[Mike Birbiglia]

Yeah.

[Questlove]

And then he realized that was going to be a very short window because as time moves on by the late 70s, early 80s, then suddenly the early 60s Motown, the big chill, Beatles mania, you know, starts to kick in.

[Mike Birbiglia]

Yeah.

[Questlove]

So as a result, my dad's like, okay, I got to get off the oldie circuit and get my nightclub circuit now. If you want to go out for a night of dancing, you'll ask, oh, who's DJing? And you go to a club and see them DJ.

[Mike Birbiglia]

Yeah.

[Questlove]

But in the mid-70s to, you know, mid-80s, bands were still pretty much part of nightclub culture. So my dad started a nightclub act and I'll say twice a month we would go binge shopping where literally we just go to the wall. I'll take that, you know, be like $400. We'll take home boxes of records.

[Mike Birbiglia]

Yeah.

[Questlove]

And then my dad's band would rummage through the box of 45s and albums, whatever the hit was. Okay. The Hustle. Oh my gosh, Casey and the Sunshine Band will take that. And whatever wasn't good.

[Mike Birbiglia]

I just get everything else.

[Questlove]

Yeah. So I'm probably the first music expert that gravitated towards the Flop song.

[Mike Birbiglia]

What's the Flop song?

[Questlove]

I always say this. So, okay, so Van McCoy had a very big hit in the 70s with the hustle. But then his follow up song Changed with the Times was a dud. So of course the band would take. We'll take the hustle 45 and learn this. And yeah, man, you could take the trash. So I would. Whatever the flop was in that artist's catalog.

[Mike Birbiglia]

Yeah.

[Questlove]

That will wind up in my record collection. Cuz the band didn't want it. And so I just. When you're, when you're between 1 and 16, you're not cynical, you're not discerning, you just. You own a record.

[Mike Birbiglia]

Yeah, yeah, sure.

[Questlove]

And so I, I, it was a long time before I realized that a lot of my favorite songs growing up were flops.

[Mike Birbiglia]

Yeah.

[Questlove]

And songs that people didn't like, so.

[Mike Birbiglia]

But that people didn't like.

[Questlove]

But that kind of raised me now where, like, I think it's Captain Obvious. Like if I play a hit, it's because I know, okay, this check's pretty big, so I better play some songs that people.

[Mike Birbiglia]

Right. They're paying you well. Like, yeah, you should throw in, hey, yeah.

[Questlove]

Something that people know.

[Mike Birbiglia]

Yeah, yeah.

[Questlove]

But yeah, I'm the guy that's always trying to trick you or figure out ways to trick you into a song that you didn't know was a danceable song.

[Mike Birbiglia]

Well, the beginning of the first six minute sequence in the SNL documentary is a DJ exercise. Right?

[Questlove]

It is.

[Mike Birbiglia]

Just to talk people through it in like layperson's terms. The first six minutes is. It's on Peacock. It's streaming on Peacock.

[Questlove]

Yeah.

[Mike Birbiglia]

The first six minutes is almost like a short film unto itself on its own.

[Questlove]

Right.

[Mike Birbiglia]

Because it's basically a DJing of some of the best musical performances in the history of snl. And what, as a collaborate together and sing. Exactly. And as a layperson, I'm just going, oh my God, this song is related to that song.

[Questlove]

So. Okay, so what's behind us? And can your viewers see your, the.

[Mike Birbiglia]

Board, your board over here? Yeah, they can sort of. I mean, they can't See the words? But like. Yeah, right?

[Questlove]

But yeah. This is literally. I'll say. It took 11 months to make that montage.

[Mike Birbiglia]

Oh, my gosh.

[Questlove]

Shout out to John McDonald, also like a master editor. It helps when your editor is also a musician.

[Mike Birbiglia]

Yeah. So it's like cards on a board. This song, this song, this song.

[Questlove]

Cards on the board. Like CSI style. Like, whenever I hear a song, the first thing I say to myself is, what key is this in? How many BPMs?

[Mike Birbiglia]

Okay.

[Questlove]

It's like an obsession. I'll pull out my iPhone, go my BPM.

[Mike Birbiglia]

How many beats per minute?

[Questlove]

Counter. Right. So I'm like, okay, well, this song's 103bpms and it's in E minor. And if there's a bridge to it.

[Mike Birbiglia]

Yeah.

[Questlove]

Ah, like, great example. Figuring out. And this is John McDonald's. I can't take credit for that. Him knowing that the course of Walk this Way, which is in C, which is different. The actual Walk this Way songs in E. Yeah. But when they go to Walk this way, talk this. That's in C minor. And somehow he figures out the two seconds that will connect Walk this Way to Cher's I Found Someone.

[Mike Birbiglia]

Yeah.

[Questlove]

And she just happens to say the words when you walked away. So that's even a double. Like, as a key, they're both married to each other, but as a subject, lyrically, they fit. Lyrically, it even fits. And so, I mean, that's what took 11 months. Because we just wanted.

[Mike Birbiglia]

That sequence is as good as any six minutes of anything I've ever seen.

[Questlove]

And then no one sees Hanson coming at all.

[Mike Birbiglia]

Hanson's great. And then, honestly, you're watching it going, hanson's pretty good. Yeah.

[Questlove]

Oh, you picked. You picked the right eight seconds to be like, let me. I actually did that. Like.

[Mike Birbiglia]

Well, the perfect example of the DJ song where you go, oh, um, Bob is pretty good.

[Questlove]

Well, yeah, as a dj, I listen to songs as a dj. It's been a long time since I listened to music for pleasure, which is also a hard thing to do. Like, what happens when the thing that gave you pleasure becomes your job?

[Mike Birbiglia]

Oh, man.

[Questlove]

And then you become numb to, like. Let me just put this on. Because I used to like this when I was a kid. So it's. It's hard to do that. But, yeah, it's. For me, I wanted to just. I mean, SNL's. SNL is only good as it's cold open. And you need a powerful cold open before you tell a story.

[Mike Birbiglia]

That's right.

[Questlove]

So I figure that's the Best way to tell a cold open.

[Mike Birbiglia]

Support for working it out comes from Mint Mobile. If you're still overpaying for wireless, it's time to say yes to saying no. At Mint Mobile, their favorite word is no. No contracts, no monthly bills, no overages, no hidden fees. No bs. Here's why I said yes to making the switch and getting Premium Wireless for 15 bucks a month. I tour the country. I tour the world. I've been super satisfied with Mint Mobile's coverage. Trust me, I know what it's like to be stranded in a broken down car in the middle of nowhere. I talk about it endlessly. It's not fun. But Mint Mobile runs on the T Mobile 5G network, America's largest 5G network. I used to have a wireless service that shall remain nameless because I thought it was overpriced and didn't provide coverage that I needed. Then I made the switch to Mint Mobile and I love it. Ready to say yes to saying no? Make the [e-mail] biggs that's mintmobile.com perbigs upfront payment of $45 required equivalent to $15 a month limited time new customer offer for three months only. This speeds may slow above 35 gigabytes on unlimited plan taxes and fees extra. See Mint Mobile for details. Working it out is brought to you by Helix. Gotta love Helix, one of our original sponsors. I've had my Helix mattress for five years and counting. Still as comfortable as the very first time I slept on it. As you know, I obsess about sleep. I think about it a lot. I've got a sleepwalking disorder, although in pretty good shape these days, and I get a great night's sleep on the Helix mattress. Here's a few things I love about my Helix mattress. It shows up in a box. I've talked about this before. Getting a mattress into your house or your apartment is a huge pain. It is a very heavy item. In this case, it shows up in a box. You open the box, Boom. You got a mattress. Let's talk about pillows. Helix makes eight different types of pillows. There's a classic dream pillow. They have cooling pillows, latex, a side sleeper knee pillow. Come on. Their pillow game is so strong. Go to helixsleep.com burbigs for 20% off site wide. That's helixsleep.com burbigS for 20% off site wide. Make sure you enter our show name Working it out after checkout so they know that we sent you helixsleep.com for bigs with summer of Soul. This is like a tiny bit of trivia. You won the Oscar, I think after the slap.

[Questlove]

After my category was the slap.

[Mike Birbiglia]

So after Will Smith slaps Chris, they, they.

[Questlove]

Now that was my cat.

[Mike Birbiglia]

The Academy Award goes to Questlove.

[Questlove]

The thing is, is that, you know, when people were first asking me, my reaction to it, I don't think they believed me when I was like, I wasn't there. Like, if you're up for anything in that level of importance, you're not in your right mind whatsoever.

[Mike Birbiglia]

Oh, right. What does it feel like? What was your headspace?

[Questlove]

Okay, so for starters, so it's a little weird when, you know, you're campaigning for a year so you're seeing the same faces of the other DOC people that you're up against.

[Mike Birbiglia]

That's right.

[Questlove]

At 40 other, you know, there's the Independent Spirit Awards and there's the, you.

[Mike Birbiglia]

Know, it's the same group of people at all the award shows.

[Questlove]

Yeah, yeah. And, you know, it gets. And we had a big year that year, so already I'm feeling like I'm the Grinch that stole awards.

[Mike Birbiglia]

Yeah, yeah, yeah.

[Questlove]

So each one, you'd won a lot.

[Mike Birbiglia]

Of awards at that point.

[Questlove]

Yeah, yeah. So I'm already just in a make it stop thing. I think, like, at one point I told Zara, my manager, like, can you ask the Disney people, like, to pull us out of, you know, like, can we pull out of these things? Because, you know, the thing is too much, like, I don't want people to not like us, you know, because, yeah.

[Mike Birbiglia]

It'S the sly in you talking.

[Questlove]

Yeah. Like, I wanted it self saboteur. Right.

[Mike Birbiglia]

And so please don't let me win the Oscar.

[Questlove]

There was about maybe I'll say the first half hour just sitting there and all the anxiety of it all. And this is like the last part of the journey. Like, it started with the sun, Sundance, the year before. And that entire year of just going through that process and you're just sitting there and you're, you know, realizing that you're up against the person who's, you know, your very first documentary you ever watched on tv, right. Is like three rows up from you and, you know, are you in the same level as him? Da da da, da da. And then you're thinking about all your relationships and who's going to like you. Who's going to be your friend. Will your band like you after this? Will your family like you after this? I'm thinking about, will Thanksgiving be normal?

[Mike Birbiglia]

Oh, my God.

[Questlove]

Because you Know, at that time, it's. It's in. You know, could happen to you, too. Like, you know, like, oh, Mr. Hollywood. And no, no. I'm sure you have that one person that doesn't know how to. To act now that you're in this phase of your life.

[Mike Birbiglia]

Yeah.

[Questlove]

And so I think in my mind, I was just sitting there, like, frozen, totally channeling out what was happening, because we're in the back row, and it's never going to be the same. Never going to be the same. Never, never going to be. I was like, wait, are they allowed to curse on tv, Mom?

[Mike Birbiglia]

When I heard the word, oh, my God.

[Questlove]

Then I stopped. It was like, I looked at my mom, like, wait, they're allowed to curse on television?

[Mike Birbiglia]

Oh, my God, that's weird.

[Questlove]

And then I just went back to, oh, God, it's all gonna be different. It's all gonna be different. Summer Soul is all gonna be different. And I stood up, totally not registering what really happened. Cause even then, I just thought, man, that was a poorly executed sketch. Right.

[Mike Birbiglia]

That's what I thought.

[Questlove]

I thought it was a bit.

[Mike Birbiglia]

I thought it was a bit.

[Questlove]

Right. But when you're walking and you're walking slow, you're already walking with this whole, did I deserve this? Did I not deserve this? Is everyone happy for me? And the way that people are clapping was more like, send for help. Cause they're right.

[Mike Birbiglia]

They're experiencing the drama of the slap that just happened that you barely even clocked.

[Questlove]

Exactly. And there was one point when I looked at. I looked at the Williams sister. Like, I don't know if my mind. I don't know if my mind. I was expecting, like, the, you know, the ticker tape. He's a jolly buffello thing, like, where people stand up and, you know, like, you know, like that. Like the heroes walk.

[Mike Birbiglia]

Yeah.

[Questlove]

But definitely people were, like, clapping like this. Which only to me was registering, like.

[Mike Birbiglia]

Like, it's about you.

[Questlove]

This is my worst nightmare. No one's happy for me.

[Mike Birbiglia]

Yeah. All of your anxiety of, are people gonna like me anymore? And then people are confusedly clapping about something that had nothing to do with you, and you don't even fully clock what just happened.

[Questlove]

Yeah, I didn't clock what happened. And then I get to the front, and there was kind of a moment where I knew my back was to the audience, to the cameras, and I knew I had about a good three seconds to ask him. I said, was that a sketch? Was that real to Kress? He's like, no.

[Mike Birbiglia]

Oh, my God.

[Questlove]

And that Moment.

[Mike Birbiglia]

Oh, my gosh.

[Questlove]

I turned around and realized, oh, my gosh. Oh, God, that shit. That was real. And it was never. And it was never My thing was never about, like, your moment got taken away from you. That was your glory moment, you know, because actually, at the time my ex told me, she said, congratulations, you got exactly what you wanted. So I'm thinking in terms of like, oh, you mean the Oscar? He says, no. He's like, this whole process watching you this entire year of you scared of your own shadow. Like, you told the universe, yes, I would like to win it, but I would want to win it in the most quietest way possible on your own terms. So this is how I learned the term. You can manifest something. You can manifuck something. So she's like, you got your man a fuckwish. You wanted to win this Oscar in the quietest way possible, where nobody's gonna judge you or be angry with you. And you asked the universe to make it happen. And that's exactly what happened.

[Mike Birbiglia]

That's really interesting. Cause it's like my experience of writing. Don't Think Twice. A lot of it was. It actually cured me of jealousy. Because what I realized about jealousy is if you want something that someone else has, you can't just one for one have what they have and be you at the same time.

[Questlove]

See, I knew that you would eventually let out and share. So now I really gotta ask you. I was waiting for you to open the door. Cause I still watch it obsessively. Like. So was that. Did at one point you try to fit into the 30 Rock ecosystem either as a writer or to some degree?

[Mike Birbiglia]

Yeah, yeah.

[Questlove]

How hard is it to get in that system? Oh, I mean, I feel like a Nepo baby. That was just ushered in because, no.

[Mike Birbiglia]

I. I wasn't one for one with snl. Like, I. I wasn't even close to snl. Like, they, Like, I. They didn't even. I didn't even audition. So the whole acting out of people auditioning. But the part that I relate to is that when I was coming up, I moved to New York in 2000, and I had been working the door with the DC Improv, and I. All of a sudden, the people who were getting heat all around me, I was like, wait, but I'm as funny as these people. And then people are blown up. People are getting snl, people are getting the Daily show, all this shit. And it's like. And it's a weird experience to feel that.

[Questlove]

So when you first start, your first job is so Any person working the door.

[Mike Birbiglia]

Yeah.

[Questlove]

Or any person. Like, that's. That's the entry. That's the intern level of getting into.

[Mike Birbiglia]

That system in some ways. Yeah.

[Questlove]

Okay.

[Mike Birbiglia]

The comedy club system. I was working the door for like, three years at the DC Improv. First person I ever opened for, actually, was Chappelle.

[Questlove]

Really? Okay.

[Mike Birbiglia]

He was 20. He was 24. I was 19. He was headlining comedy clubs nationwide when he was 24 years old.

[Questlove]

And is that unusual?

[Mike Birbiglia]

Yeah, it's almost unheard of.

[Questlove]

Really? So you have to be almost like an experienced.

[Mike Birbiglia]

Yeah.

[Questlove]

Really?

[Mike Birbiglia]

Yeah, it was a bizarre. It was just about. It was when Half Baked was just about to come out.

[Questlove]

Funniest script I've ever read in life. Side note. So all the music for season two of Chappelle, that's when they hired me. Doing Chappelle is what got me the Tonight Show. But, yeah, I was the musical director of season two and very little of season three that happened. And I gotta tell you, I had that Ricky James sketch a good five months before it came out.

[Mike Birbiglia]

Oh, you had seen it.

[Questlove]

Dude. Do you know how crazy my life was where I would actively. I would go to parties and have that script in my bag.

[Mike Birbiglia]

Oh, my God.

[Questlove]

And I would perform it for people as a one man show.

[Mike Birbiglia]

Oh, my God, that's so funny.

[Questlove]

The. I would say the highlight of my social celebrity standing.

[Mike Birbiglia]

Yeah.

[Questlove]

Like, Amir, he's so funny.

[Mike Birbiglia]

Like, literally, Amir is so funny.

[Questlove]

Yo. I knew that whatever those guys were gonna shoot wasn't gonna be half as funny.

[Mike Birbiglia]

Yes.

[Questlove]

As what I was doing at parties every night. And I perfected it. I would add my own things to it, like, memorized it, like. Yeah. You know, I worked at the Chappelle Show. We're doing this thing about, you know, Rick James, like, you know, and his arguments with Charlie Murphy and. Oh, wait, I think I have it right here. And then I started reading it. Can you imagine.

[Mike Birbiglia]

Support for working it out comes from Rula? Look, finding a therapist is hard. Just ask me. I've had two therapists over the many, many years. Finding one that takes your insurance is even harder. And we never talk about this. Sometimes keeping a therapist can be hard. This happens sometimes against all odds. You find a therapist who takes your insurance and then they change offices and they. Or they retire or they die. I mean, that's. Another friend of mine had that happen. That's a whole deal when your therapist dies. That can happen. Natural causes, you know, or they don't do virtual appointments. All these things happen. But with Rula, you can avoid these problems because Rula is an online therapy platform that partners with a network of over 15, 000 therapists and psychiatrists nationwide, enabling you to find your personalized solution and the right therapist for you based on your needs, preferences and state requirements. Thousands of people are already using Rula to get affordable, high quality therapy that's actually covered by Insurance. Visit rula.com for Biggs to get started. After you sign up, you'll be asked how you heard about Rula. Please support our podcast and let them know that we sent you. That's rula.com r u l a.com p I r B I G S. You deserve mental health care that works with you, not against your budget. Support for working it out comes from Quince as the weather cools, it's time to put away all the warm weather clothes I got from Quint and start layering up. Quint has a fantastic fall collection. I love the Mongolian cashmere sweater. It's just a personal favorite. It's a perfect fall clothing item. The right feel, the right temperature for crisp fall days. That runs about 60 bucks. I'm happy knowing it's money well spent because the clothes last. I know I'll be rocking this cashmere sweater next fall and the fall after that and for years to come. Their fall collection also includes a suede tracker jacket, wool blazers and more. Really love this site. It's great layer up this fall with pieces that feel as good as they look. Go to quince.com for bigs for free shipping on your order and 365 day returns now available also in Canada for our Canadian listeners. That's Q I-N-C-E.com b I R-B-I g s free shipping and 365 day returns. Quince.comigs this is a slow round and actually fitting from what we were talking about. Who are you jealous of?

[Questlove]

Oh God, do I have to give a proper noun? I don't know.

[Mike Birbiglia]

Do I have the the follow up question is who are you jealous of? That you you thought of but you didn't say.

[Questlove]

You know, I'll tell you that the kind of boo hoo woe is me positioning that I took with the roots when it came time to like is this gonna be our turn? Is this gonna be our moment?

[Mike Birbiglia]

Yeah.

[Questlove]

You know when our cause, the thing was we were critically acclaimed. But critically acclaimed doesn't necessarily mean that we're hip makers.

[Mike Birbiglia]

Right. You're beloved.

[Questlove]

Yeah. And kind of in the rap game. You have to be A hip maker.

[Mike Birbiglia]

Right.

[Questlove]

Like, so we totally. I will say that I'm proud to say that a lot of our surviving was just being prestige artists. Like, but it was almost to the point that people thought we wanted to be prestige artists, where they would just be like, well, you guys don't care about, like, hit singles and going platinum and everything. And inside my voice I'm like, I do care about that shit.

[Mike Birbiglia]

That's so good.

[Questlove]

So, you know, I will generally say that. Yeah. In 96, when the fugees are having their moment.

[Mike Birbiglia]

Oh, yeah.

[Questlove]

You know, huge. I. I might have sat in a bathtub, like, fully clothed, like, looking at their Rolling Stone cover with my darts. Like, you know, And, I mean, it happens with every cycle. Like, there'd be moments where I, you know, and I absolutely love the Fugees. Like, we had some of the best times touring and all those things, but, you know, at the point when they're like, selling 12 million and, you know, congrats, guys, you just broke 300,000. And it was just like, we're never going to make it. So there are moments with that. And then, like, in 98, when our own came out, like, okay, it's about us. And then outkast is like, nope, hang on, hang on. Our turn now.

[Mike Birbiglia]

Oh, my God.

[Questlove]

So, yeah, I always felt like back then, I felt like we were Rudolph the Red Nosed Reindeer, like, not allowed to play in reindeer games.

[Mike Birbiglia]

I love that.

[Questlove]

But I will also tell you, some 32 years and 17 albums later, looking in the rear view mirror.

[Mike Birbiglia]

Yeah.

[Questlove]

Of what's happened to everyone. This. This was absolutely, positively the best storybook ending ever. Like, I'll ask you. I don't know what the equivalent of asking you, would you rather your second album sell 12 million units and you win a whole bunch of awards, and then you just have the craziest crash and burn of all time? Or would you rather tortoise and hare your way? Even when you pass the finish line, you don't realize that you've made it.

[Mike Birbiglia]

I thought I wanted the first one, and I know now I wanted the second one now that I've had the second one. Because when I was in my 20s, I was the. I was like, yeah, I want to be.

[Questlove]

Want to be a famous and.

[Mike Birbiglia]

Right, right. Yeah. And then now I'm 46. I'm just like, oh, this is great. I go to every city, people show up, they want to see what I'm doing. They don't want to see me because I'm known from something that isn't me. They like what I'm doing, and it's like, oh, my God. That's the greatest gift. It's the people who listen to this podcast, you know, the greatest gift you could possibly imagine in. In exchange for giving yourself to your work.

[Questlove]

I said, so I sat there in the audience. I saw your show the Beacon, and the Beacons are, you know, that's a big deal. Like, I remember playing that when I was, you know, my dad played. I think I played the Beacon when I was 12 with my dad. So I know that dude. I was his band leader when he.

[Mike Birbiglia]

No, it's a big deal. I did it when I was 12.

[Questlove]

Well, I don't count anything when I was 13.

[Mike Birbiglia]

I did Madison Square Garden.

[Questlove]

I don't count anything I did Yankee.

[Mike Birbiglia]

Stadium when I was 15. Beacon's a big deal.

[Questlove]

Anything with my dad. Look, I just happen to be there. I just happen to be there. But, you know, it's a historic fan. I am. Yeah, it is. And I. It's. It's hard to. In hindsight. Yes. The Tortoise and the Hare Journey.

[Mike Birbiglia]

Yeah. So you're ha. You're happy with that version of it?

[Questlove]

I'm happy with it, but I also. You know what I am. I'm the person. Okay. Speaking of Will Smith, I'm the person that once asked Will Smith, like, the story of how he jumps from the Fresh Prince to the Fresh Prince of Bel Air. Going from the Fresh Prince to Will Smith was a move in which he didn't consult anybody, really. Right. So the quickest story is that he, you know, they had this incredible success with their second album. He's the dj, I'm the rapper. They sell millions of units. They're really just benefiting the. The, The. The. The. The waterfall of. Of YOMTV raps.

[Mike Birbiglia]

Right?

[Questlove]

Anything on YoMTV raps between 88 and 90 is just. It's now reaching Middle America and everything.

[Mike Birbiglia]

Yeah, yeah, sure.

[Questlove]

So they benefited from that. So when their next album comes out in this corner, which I actually love better, it flopped, but they still did the rounds of promotion and all those things. And they did the Arsenio hall show and did a really compelling performance of I Think I Can Beat Mike Tyson. That was the first single from that thing. And Quincy Jones happens to watch it. And Quincy Jones rings up super manager Benny Medina, who is the Fresh Prince of Bel Air.

[Mike Birbiglia]

Okay.

[Questlove]

Medina tells Jones's life story about being, like, a Barry Gordy of Motown's assistant and how he came up in. In Hollywood and how he so his Benny Medina, who's JLo's manager, is the Fresh Prince of Bel Air. So that's about his life. Oh, interesting, right? So Will Smith, not knowing what he's getting called to come to Quincy's house for, he thinks he's going to Quincy Jones's birthday. And it's Quincy Jones's birthday. This is crazy story is Quincy's birthday. And, you know, a couple bottles later and everything. And everybody's like, he's, hey, Philly, come over here. He's just calling him Philly. Not even like, will. He says, you know, I saw what you did on a city owner. You know, that man is over there. He's like, his name is Brandon Tartikoff. We're going to do something just real quick. And he pulls out a script, and then. And he makes Will Smith audition in front of, like, Oprah Spielberg. Like this.

[Mike Birbiglia]

Start at the party.

[Questlove]

At the party.

[Mike Birbiglia]

No. What are you talking about?

[Questlove]

And Will's like, yo. Like, well, wait, I need, like, two weeks in.

[Mike Birbiglia]

What a weird birthday party.

[Questlove]

And literally, Quincy Jones is like, the three men that can greenlight this deal right now are in this room. Just read the script. Oprah, I think she wrote read for the role of Aunt Vivienne. Like, literally, people are like, his co stars are, like established actors and whatnot. And so he does it, and then he looks at everyone's like, so what do you think? What do you think? It's like, yeah, let's do it. He's like, all right, wait, Philly, you have a lawyer yet? He's like, well, no. And he calls. Here's. It's like Bob Newhart style. He's like, yeah, what'd you. Really. Can you come by? Well, how far apart are they? Well, it's triplets. Yeah, man, I've heard that situation. It's not going to happen until another two hours. Yeah, just come by real quick.

[Mike Birbiglia]

So how far apart are they?

[Questlove]

He comes. He literally. The lawyer leaves the hospital where his wife's about to give birth and introduces him to his new client, still his lawyer to this day. It says, philly, meet you, the new lawyer. And they drew up a contract. And so I was like, wait a minute. So you flew there thinking that you're going to a birthday party. How are you explaining to Jeff and your manager and everyone else what you just did? Yeah, and for me, there have been plenty of times where I've had that moment and kind of squashed it or said, no.

[Mike Birbiglia]

Interesting.

[Questlove]

All in the name of cause again, I think the Human experience is, we'd rather be liked than Shine.

[Mike Birbiglia]

Sure.

[Questlove]

And so, yes, I will say that I believe that Tortoise and the Hare journey is the best journey.

[Mike Birbiglia]

Yeah.

[Questlove]

But part of me does wonder, what if you did take that audition?

[Mike Birbiglia]

Yeah. Yeah.

[Questlove]

What if you did that? Like, I didn't want to do Summer Soul. Like, you're saying it took seven months for them to finally, like, talk me into doing that? I didn't want to do it.

[Mike Birbiglia]

Wow.

[Questlove]

Why would I want to do that? I can't do that. I can't do that. And then you start talking yourself into. If you say it, it happens.

[Mike Birbiglia]

So in that way, you're like the Gillian Jacobs character in the movie.

[Questlove]

That's why I obsessively watch that movie. Michael Biglia. Yes, exactly.

[Mike Birbiglia]

But the Gill. But to the point of you being like the Gillian character, which is someone who's true to yourself and authentic and uncompromising to a degree, I guess my question is.

[Questlove]

You still say that. I still disagree, but go ahead.

[Mike Birbiglia]

Okay. But my question is, and because a lot of creatives listen to this show, they had to convince you to do Summer of Soul, and it ended up being this huge triumph. How did you get from not wanting to do it to being like, no, I'm gonna go all in on this? What is that journey? Because that's, I think, something people struggle with all the time.

[Questlove]

I stopped kicking and screaming. I'll say that around, like, 2018, 2019 is when I started realizing, well, one thing. Watching people get in their own way, watching people self sabotage. There's a moment where I realized, wait, is that me, too? It's easy to do this.

[Mike Birbiglia]

Yes. Yeah.

[Questlove]

Point fingers and, you know, see, they're always messing up. They're always messing up. And I didn't realize that for myself. And, you know, kind of one of my. I realized that I made a life being a second banana. Hiding behind a DJ rig, Hiding behind a drum set. Hiding behind Tariq. Hiding behind Jimmy.

[Mike Birbiglia]

Yeah.

[Questlove]

Mammoth. Text and post on Instagram. Writing books.

[Mike Birbiglia]

Yes.

[Questlove]

With the exception.

[Mike Birbiglia]

I love those. I love those posts.

[Questlove]

With the. With the exception of me teaching at NYU the first time I. We have a friend, Seth Herzog.

[Mike Birbiglia]

Yeah.

[Questlove]

And when I accepted teaching at nyu, he got in my head, like, three weeks before, like, man, so you're about to be a professor at nyu, huh? I was like, yeah. You know, he's like, so what are you going to do? Like, someone pulls out their phone or something. And I was like, well, what do you mean? He's like, well, you're dealing with kids, like, do you know how to handle, you know, someone that talks too much? Da, da, da. And that's things I didn't think of. Like, I. I just thought, like, I'm gonna go in and teach. And, yeah, the day to day of it all, 30 of them will be recept. No one's gonna be disruptive or ask a bunch of questions or be a problem. And he got in my head about that, and I realized, oh, God, this is the first job I ever had in which I don't have a shield to do the dirty work for me. Like, Tariq has to face the audience and talk to them. Jimmy has to face the audience every night. So I realized there's a level of leadership vulnerability that I've been avoiding by hiding in plain sight.

[Mike Birbiglia]

Yeah.

[Questlove]

And so, you know, I had to make a decision, probably late 2017, early 2018, where it wasn't serving me to hide in plain sight. And on top of that, where I think I wanted to go in life, I'm going to have to drop something in order to get it. And so I had to stop being the reluctant, you know, person. You know, the person too cool for school.

[Mike Birbiglia]

Yeah.

[Questlove]

Says, no, first before. I ain't doing that. That's dumb. You know, And I had to examine, like, why do you think that's dumb? Because you think. Or you think the guys are going to make fun of you because you went to da da da da da. And, you know, so I had to let that go. But it's. It's an everyday battle, almost like. Yeah, it's an everyday battle. Like just waking up every day and, you know, I have to. I do a morning routine.

[Mike Birbiglia]

Yeah.

[Questlove]

Where second I get up, I spend 20 minutes. Literally, like, my version of Eminem's opening scene in 8 Mile, where you just gotta, like, look in the mirror and talk to yourself and all that shit.

[Mike Birbiglia]

So, yeah.

[Questlove]

Yeah, I do it.

[Mike Birbiglia]

What's the best piece of advice someone's given you that you used?

[Questlove]

Who? All right. If a person asks me, like. Or is wondering, because that's the thing, it's like, wait, what are you still doing here? I get that a lot. Because I don't have the same numbers on the board as established people, especially in my field of hip hop, but I've spent 20 years of somehow getting that. Oh, surprised you're here. Like, wait, you're here too?

[Mike Birbiglia]

Yeah.

[Questlove]

Like, how did you get in? I love that whole thing. I show up.

[Mike Birbiglia]

Yeah. Yeah.

[Questlove]

Which I know that doesn't sound like sage advice. Or whatever. But if you look at the amount of people, like, a lot of things I just show up for is because someone else didn't show up for it. And I know I'm the fifth person or the sixth person, but you just have to show up.

[Mike Birbiglia]

Yeah, that's right.

[Questlove]

I don't think it's talent or I think I do that as a psychological insurance plan.

[Mike Birbiglia]

Yeah. Like, okay, well, it's so easy to not show up. It's so much easier to not show up.

[Questlove]

But again, I, I tell people from the mountaintops, like, I know I give the impression that it's like, oh, it's supposed to be about this mental musical intelligence or, well, he has so many records and he studies music and that he knows all these obscure records. And none of that helps. Like, none of that helps. Especially what I'm doing now. Like, there is no training for what I'm doing. I'm literally learning every day the art of storytelling and putting. Even though I have the experience of making records, making movies is an entire telling stories is entirely different medium. And so you just have to show up.

[Mike Birbiglia]

So the final thing we do is working out for a cause. Is there a non profit that you like to support? And we will contribute to them and then link to them in the show notes.

[Questlove]

I appreciate this. There is a group of kids, they are students at the food and finance business school, which is like the weirdest title ever for what it really is. This food, this, this high school is the culinary version of the LaGuardia School. Think of everything that you know about a fame school. But instead, in addition to their basic classes, they learn how to bake, how to make sushi, how to do irrigation systems, how to work with plant food and indoor farming.

[Mike Birbiglia]

Wow.

[Questlove]

How to. And it's, it's a passion of theirs. Like when it first opened, it was more like, well, you know, these students are the, the lowest testing score of, of all of Manhattan. So let's at least do home economics to school. Maybe they could be a maid in a hotel or work at a McDonald's.

[Mike Birbiglia]

Right.

[Questlove]

But the opposite happened and now a lot of our students are discovering their culinary passion. And yeah, they attend the food and finance business school, which is essentially the food version of the fame school.

[Mike Birbiglia]

Wow.

[Questlove]

Yeah.

[Mike Birbiglia]

That is so cool. So we're going to contribute to them. We'll link to the show notes, encourage people to contribute as well.

[Questlove]

Thank you. I appreciate it.

[Mike Birbiglia]

Amir, it's been an honor.

[Questlove]

Thank you for having me.

[Mike Birbiglia]

You're wildly inspirational. I'm going to go work on writing my third movie right now because I Everything you say fills me up with inspiration, so I feel lucky to know you.

[Questlove]

Well, I'm a fan of the show and I'm glad to be on. Thank you sir.

[Mike Birbiglia]

Thanks Doc. Working it out because it's not done. We're working it out because there's no that's going to do it. For another episode of Working it out, you can follow Questlove on Instagram Questlove. You can check out his documentaries on snl, Music on Peacock or Sly Stone on Hulu or Disney. I highly recommend them. You can watch the full video of this episode on our YouTube channel. My YouTube channel is Mike Birbiglia. Check that out and subscribe. We are posting more and more videos. Check out birbigs.com to sign up for the mailing list and to be the first to know about my upcoming shows. Our producers of Working it out or myself along with Peter Salomon, Joseph Birbiglia and Mabel Lewis Associate producer Gary Simons Sound mix by Kate Belinsky. Special thanks to Jack Antonoff and Bleachers for their music. Special thanks as always to my wife, the poet J. Hope Stein and our daughter Una, who built the original Radio 4 made of pillows. Thanks most of all to you who are listening. If you enjoy the show, please rate us and review us on Apple Podcasts. It really helps out. And if you're new to the podcast and enjoy this one, we have over 160 more episodes that are evergreen and not behind a paywall for the last almost five years. They're all free. We've had Rachel Feinstein and Jimmy Fallon and Roy Wood Jr. And so many great folks. Check out our back catalog comment on Apple Podcasts, which is your favorite that helps people find it. Thanks most of all to you are listening. Tell your friends, Tell your enemies. Let's say one of your enemies is self sabotaging. They could be achieving more and they could be nicer to people and you just know it deep in your soul and you think, I want more for my enemy. And you could say to your enemy, hey, I know this podcast where Mike Birbiglia and Questlove talk about this exact thing. And you could watch a documentary after that that's exactly about that theme and maybe that enemy will come around and maybe not be your enemy anymore. Thanks everybody. We're working it out. We'll see you next time.

[Questlove]

Sa.