Mike Birbiglia's Working It Out - Questlove: The Art of Self-Sabotage

Episode Date: October 6, 2025

Best of WIO: Questlove(Recorded April 2025) The legendary Ahmir Thompson (aka Questlove) sits down for his first appearance on Working It Out. Mike and Questlove discuss touring with his father’s band as a kid, every DJ’s worst nightmare, and how jealousy and self-sabotage can affect even a member of a band as iconic as The Roots. Plus, what it was like accepting an Oscar after The Slap and the behind-the-scenes process of Quest’s new documentaries Sly Lives! and Ladies & Gentlemen... 50 Years of SNL Music.Please consider donating to: The Food and Finance High School Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Who are you jealous of? Oh, God. Do I have to give a proper noun? I don't know. The follow-up question is, who are you jealous of that you thought of, but you didn't say? That is the voice of the great

Amir Thompson, aka Quest Love. 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 miss 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, who's nominated for the SNL music documentary, which is unbelievably good. I mean, actually, the Sine 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 on 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, really, really good jokes. But we have a great talk with Questlove today, massive fan of Questlove. We talk about his music and documentaries about SNL and Slice Stone. Enjoy my conversation with the great Questlove I think with comedy

you don't have the same relationship with mistakes that musicians do whereas you know playing like an amateur playing people say something wrong when I play it right like there are roots guys know I'm mad when I play everything correct

that's great Like, oh, what's wrong with you? Right. I'm cool. A headache. You know, like, that sort of thing. That's great. That's funny because 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. I learned that it all came together probably in the first year of, and I never say, like, my life won 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. Right. 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. So being in the building, you think, was that first, created the first epiphany about that? That was the first green light I had. Wow. And this all ties them together. Because even with, you know, like 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. Yeah. Like, 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. Okay, so to give everyone. context yeah uh when you you did my podcast god like 10 years ago yeah that's right oh this is this is a slow turnaround yeah like 10 years supreme yeah yeah that's right right

right so when you my theory was that when i saw when i when i when i 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. Yeah. 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 and 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 that's right at large so that's where we disagree because you told me that you felt that they were fully aware that they knew what their limitations were and that they were comfortable this is where we disagreed about my movie right because because the thing is is that i i believe that most people self-sabotized you know because we want to control we want to know what's next you want to know what the next step is

right solid ground or is this you know a quickstand and not having the the comfort of the know know how of knowing uh if you're going to drown or not yeah makes people just say okay no nope this is where i get off this is where i'm going to say this is right so in other words they're controlling their own kind of decline because they're afraid that maybe the incline isn't there? Yeah, I mean, declines are familiar. Letdowns are familiar. Disappointments are familiar.

Yes. As opposed to success. That's right. 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. So this is a, so in your documentary, Sine the Family Stone documentary, Sly lives, the person who I think is in some ways the hero in addition to the director is, 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 and 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. 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. Oh, interesting. I kind of had to Jedi mind-trick people. We had the Jedi Mind-trick people. The life of a documentary film. filmmaker. You have to trick, semi-trick people into making what you want to make. 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, your tendency to keep people waiting for 12 hours or your tendency to wait decades between records or your tendency. So you interviewed a bunch of some people like DeAngelo and others who have. of similar self-defeating tendencies. Yeah, I joke that there's the exact moment where DeAngelo 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, uh, yeah, yeah, yeah. I knew this was a trap. I knew this was a trap. But I, you know, I had to... Oh, that's so funny. 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 coming or not?

How many people didn't show up? We got stood up maybe three times. Oh, that's not bad. but yeah there were 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 that's really interesting yeah yeah so with sly do you know if he's seen it yeah he's he's seen it absolutely do you know if he likes it yeah he he likes it i know Traditionally, especially with documentaries, the subject is not supposed to be the executive producer or have say in it.

Yeah, yeah. But it's kind of weird because in this specific case, with the music copyright and all those things, you know, the Jackson Estate owns the sly songs. Oh, they do? So, 1984, in 1984, no, no, it was the smartest business move Michael Jackson ever made. I know, he bought up a bunch of stuff, right? Bought up a bunch of Beatles stuff? 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. That's crazy. But, you know, you're supposed to buy, like, some songs. Mike's just like, oh. I'll buy the entire house. Right. I'll buy the Beatles.

Yeah, in 83, he purchased ATV publishing, which is one of the biggest publishing houses. It's Chuck Berry songs, Sly's songs, the Beatles songs, Little Richard songs, da-da-da-da. And, you know, just in general, 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 going to do is go to them to see 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. It was basically to show people kind of what artists go through but in a way that it didn't feel like you know the world's tiniest violin so for me

it was important to show it in a way that didn't wreak of all poor baby but really just like explain to you what the level vulnerability that it takes to be that person do you I mean your your personal story is not that dissimilar from sly

in the sense that you're both musicians you're both DJs. 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 the radio DJ. 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 DJ, of him DJ. 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? Yeah. Okay. So in my mind, my thing is, how am I going to connect Benny Goodman and Kenjik Lamar? Exactly. And by the way, if people haven't seen this, they should watch your master class on DJ.

I totally forgot. I had that thing. I mean, it is, it opened my mind to even the art of what DJing is. Like, I didn't understand it before that documentary. 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 midset to say, excuse me, excuse me, excuse me, hey, tell the chicken cross the road, can you do that one? You tell the shit you cross the road joke. 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 goes up to the DJ like, hey, could you believe it? Yeah. 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 going to play. like, you know, the temptations and even like Dyke in the Blazers, funky Broadway, you know what I mean? Like, and that was sort of unheard of, like, mixing, mixing rock and soul on the same radio station, like, that's not supposed to happen.

So what you're not supposed to do, he's, and so, you know, he's probably just as a human contrary to start with, whatever he's not supposed to do. you're doing. Yeah. 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 shows you DJs, 901, you know, think about how, like, Robin Williams acts, like 12 characters at once in a, yeah, man, yeah, man, that was sly. He would make his own commercials up for products that don't exist.

Yeah. Or, you know, like, hmm, let me do a commercial for a tidy bowl. Like, and literally he would make his own commercials. So even then what will happen is those 9, 10, 11, 12, 13-year-olds in 1960 will now be the counterculture hippies in 67, 68, 69. Yeah. Kind of the, what you know as the Bay Area hippie or the counterculture person, like Sly had a major hand and raising them. Yeah.

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 i couldn't believe it when i saw that he produced somebody to love yes i was like what yeah so basically one of the biggest rock hits of all time 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 in the family stone yeah and so yeah it would seem rather up his alley you know it was funny because um When I did The Old Man in the Pool at Lincoln Center, I had just seen your master class 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. 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, because you sent it as like a 45-minute file. Oh, you thought I was just going to feed you songs on your Spotify? 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? So right about now, so I'm in a weird, I'm in the third phase of record collecting. So I've been 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. We got to learn celebration by Koolnik gang. So since... For real? Like, that was his job? Well, yeah. So my dad was an oldies duop singer in the 50s on chess records, like back in the 50s.

Wow. By the time I was born, the first wave of nostalgic 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. So you were thrust into like professional music. music when you were a kid.

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, Brooks Shields tell stories of, like, yeah, I was at Studio 54 when I was 12 and 13. Scandal culture or outrage culture didn't really kick it until, like, the late 80s. Yeah. You know, with, like, doing the gym and Tammy Fay Baker, like, you know, the clushing of

the pearls, outrage, but no one cared. So, 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. Unbelievable. 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 on in that circuit for maybe like three to four years. between like 72 to 76 maybe yeah 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 yeah so as a result my dad's like okay i gotta get off the oldie circuit and get in the nightclub circuit now deep you know now if you want to go out for night of dancing, you'll ask, oh, who's DJing? And you go to a club and see them DJed. Yeah. But in the mid-70s to, you know, mid-80s, bands were still pretty much part of nightclub culture. Yeah. My dad started a nightclub back. And I'll say twice a month, we would go bin shopping. We're literally, we just go to the wall. I'll take that, that, that, that, that, that, that, that, that, that, that, that, that, that, you know, it'll be like $400. We'll take home boxes of records. Yeah. And then my dad's band,

What 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, I'd wind up. You just get everything else. Yeah, so I'm probably the first music expert that gravitated towards the flop song. What's the flop song?

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 and changed with the time 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 right

I would whatever the flop was in that artist's catalog yeah that would wind up in my record collection because the band didn't want it and so I just when you're between

one and 16 you're not cynical you're not discerning you just you own a record yeah yeah sure and so i i it was a long time before i realized that a lot of my favorite songs growing up were flops yeah and songs that people didn't like so but that people didn't like 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

right they're paying you well you should throw in heyah yeah something that people know yeah yeah um 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 well the beginning

of the first six minute sequence in the SNL documentary is a DJ exercise right it is 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, the first six minutes is almost like a short film unto itself. On its own, right. Because it's, it's a, it's a, it's basically a DJing of some of the best musical performances

in the history of S&L. And what, as a late, collaborate together and sing and, exactly. And as a lay person, I'm just going, oh, my God, this song is related to that song? So, okay, so what's behind us? And can your viewers see your board over here? Yeah, they can sort of, I mean, they can't see the words, but like, yeah. Right. But, yeah, this is literally, I'll say it took 11 months to make that montage.

Oh, my gosh. Shout out to John McDonald, also like a master editor. it helps when your editor is also a musician yeah um so it's like cards on a board this song this song this song cards on the board like c s i style yeah like whenever i hear a song the first thing i say to myself is what keys this in how many bps okay it's like an obsession i'll i'll pull out my iPhone go my bpm how many beats per minute right so i'm like okay well this song's 103 bpms and it's in e minor and if there's a bridge to it yeah ah like great example uh figuring out and this is john macdonald's i can't take credit for that him knowing that the course of walk this way uh

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 to that's in c minor and somehow he figures out the two seconds that will connect walk this way to shares, I found someone. Yeah. 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. That sequence is as good as any single. six minutes of anything I've ever seen. And then no one sees Hanson coming at all. Oh, Hanson's great. Right. And then honestly, you're watching it going, Hanson's pretty good. Yeah. Oh, you picked the right eight seconds to be like, let me, I actually did that. Like, well, the thing. It's a perfect example of the DJ song where you go, oh, umbub is pretty good. 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 with the thing that gave you pleasure becomes your job oh man 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 want it to just I mean SNL is SNL is only good as it's cold open and you need a power powerful cold open before you tell a story that's right i figure that's the best way to tell a cold open with summer with summer of soul this is like a tiny bit of soul this is like a tiny bit of

trivia. You won the Oscar, I think after the slap? My category was the slap. So after Will Smith Slaps Chris, they, and now

that was my cat. The Academy Award. Go to Questlove. The thing is is that 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.

Oh, right. What does it feel like? What was your headspace? 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. That's right. At 40 other, you know, there's the Independent Spirit Awards and there's the, you know, the, you know, It's the same group of people at all the award shows.

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. Yeah, yeah, yeah. So each one. You'd won a lot of awards at that point. Yeah.

And so I'm already just in a make-it-stop thing. I think, like, at one point I told Zara, my manager, like, he asked the Disney people to pull us at. out of, you know, like, can we pull out of these things because, you know, I think it's too much. Like, I don't want people to not like us, you know, because. Yeah. It's the sly in you talking. Yeah.

Like, I wanted it to stop. Right. And so. Please don't let me win the Oscar. 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.

Sunday after a year before and that entire year of just going through that process and you're just sitting there and you're realizing that you're up against the person who's, you know, your very first documentary you ever watched on TV is like three rows up from you and, you know, are you in the same level as him? 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 well thanksgiving be normal oh my god because i you know at that time it's it's in you know it can happen to you too like you know like oh mr hollywood and then 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 yeah 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 a fucking

never going to be I was like wait are they allowed the curse on TV mom when I heard the word fucking oh my god then I stopped and was like I looked at my mom like wait they're allowed to curse on television oh my god that's weird and then I just went back to oh god it's all going to be different it's all going to be different summer so it's all going to be different summer so it's all going to be different. And I stood up totally not registering what really happened. Because even then, I just thought, man, that was a poorly executed sketch. Right. That's what I thought. I thought it was a bit. I thought it was a bit. Right. But when you're walking and you're walking slow, you're already walking with this whole, did I deserve this? Did I deserve this? Is everyone

unhappy for me. And the way that people are clapping was more like, send for help because they're... That's right. They're experiencing the drama of the slap that just happened. Right. You barely even clocked. Exactly. And there was one point when I looked at the William's sister. Like, I don't know if my mind, I don't know if my mind, my mind, I was expecting like the, you know, the tip, ticker tape. He's a jolly of a fellow thing like where people stand up and, you know, you know like that like the heroes walk yeah but definitely people were like clapping like this which only to me was registering like it's about you this is my worst nightmare no one's happy for me yeah all of your anxiety are people going to 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 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 audiences, 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 Chris. He's like, fuck no. Oh, my God. And that moment. Oh, my gosh. I turned around and realized. Oh, my gosh. Oh, God, that was real.

And it was never, and it was never, my thing was never about like your moment got taken away from you. Right. That was a glory moment, you know, because actually, at the time my ex told me, she said, congratulations, you got exactly what you want. So I'm thinking in terms of like, oh, you mean the Oscars? 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 that's this is how i learned the term you can manifest something you can man to fuck something so yeah she's like you you got your man to fuck wish you wanted to win this oscar in the quietest way possible where nobody's going to judge you or be angry with you and you asked the universe to make it happen, and that's exactly what happened. That's really interesting because 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. See, I knew that you would eventually let out. And share, so now I've really got to ask you, I was waiting for you to open the door. Because I still watch it obsessively. Like, so was that, did at one point you tried to fit into the 30 Rock ecosystem, either as a writer or? To some degree. Yeah, yeah.

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, I, I wasn't one. one with S&L. Like I wasn't even close to S&L. Like they, like, I 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'd been working the door with the DC improv and I, all of a sudden, the people who were getting heat all around me were, I was like, wait, but I'm as funny as these people. And then people are blowing 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. So when you first start, your first job is, so any person work in the door or any person, like, that's the entry, that's the intern level of getting into that system? In some ways, yeah. Okay.

The comedy club system, I was working the door for like three years of the DCM. First person I ever opened for actually was Chappelle. Really? Okay. He was 24. I was 19. He was headlining comedy clubs nationwide when he was 24 years old. And is that unusual?

Yeah, it's almost unheard of. Really? So you have to be almost like an experienced? Yeah. Really? Yeah, it was a bizarre. It was just about, it was when half baked was just about to come out. Funny 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 season three that happened. And I got to tell you, I had that Ricky James sketch a good five months before it came out.

Oh, you had seen it. 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. Oh, my God. And I would perform it for people as a one-man show. Oh, my God, that's so funny. I would say the highlight of my social celebrity standing.

Yeah. Like, Amir, he's so funny. Like, literally. Amir so funny. No, I knew that whatever those guys were going to shoot wasn't going to be half as funny. Yes. 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? This is a slow round and actually fitting from what we were talking about. Who are you jealous of? Oh, God. Do I have to give a proper noun?

I don't know. The follow-up question is, who are you jealous of that you thought of, but you didn't say? Um, you know, I'll tell you that the kind of boo-hoo, woe was me positioning that I took with the roots when it came time to like, is this going to be our turn? Is this going to be our moment? Yeah. You know, when our, because the thing was we were critically acclaimed, but critically acclaimed doesn't necessarily mean that we're hip makers. Right. you're beloved yeah and kind of in the rap game you have to be a hip maker right like so we totally i will say that i'm proud to say that a lot of our surviving was just being prestige artist

like but it was almost to the point that people thought we wanted to be prestige artist where they were just to be like well you guys don't care about like hit singles and yeah going platinum and everything and inside my voice i'm like mu fuck i don't care about that shit That's so good. So, you know, I will generally say that, yeah, in 96, when the Fugis are having their moment. Oh, yeah. You know. Huge.

I might have sat in a bathtub, like, fully clothed, like, looking at their rolling stone cover with my darts. You know, and then, I mean, it happens with every cycle. Like, there would be moments where I, you know, and I absolutely love. the Fuji's like we had some of the best times touring and all those things yeah you know at the point when they're like selling 12 million and you know congrats guys he 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 at 98 when I don't came out like okay it's about us and then the outcast is like nope hang on hang on oh my god oh my god so yeah I always felt like back then I felt like like

we were Rudolph the Red Nose Reindeer like not allowed to play in reindeer games I love that but I will also tell you some 32 years and 17 albums later

looking in the rear view mirror of what's happened to everyone this this was absolutely positively the best story book 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 hair your way even when you pass the finish line you don't realize that you've made it. 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, I was like, yeah, I want to be, I want to be a star. Famous. 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. It's the greatest gift you could

possibly imagine in, in exchange for giving yourself to your work. I sat, so I sat there in the audience. I saw your show The Beacon. And the Beacons, 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, like, that's, dude, I was his band leader when it. No, it's a big deal. I did it when I was 12. Well, I don't count anything. When I was 13, I did Madison Square Garden. I don't count anything.

I did Yankee Stadium when I was 15. The beacon's a big deal. Anything with my dad, look, I just happened to be there. I just happen to be there. But, you know. It's a historic thing. I am, yeah, it is. And it's hard to, in hindsight, yes, the tortoise and the hair journey.

Yeah. So you're happy with that version of it. 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. Uh-huh. Going from the Fresh Prince to Will Smith was a move in which he didn't consult anybody. Oh, 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 waterfall of YOMTV raps.

Right. Anything on YomTV raps between 88 and 90 is just, it's now reaching Middle America and everything. Yeah, yeah, sure. So they benefited from that. So when their next album comes out, in the same. corner, which I actually loved better, uh, it flopped. Uh, but they still, you know, did the rounds of promotion and all those things. And they did the Arsenio Hall show. Yeah. 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, uh, super manager, Benny Medina, who is the Fresh Prince of Bel Air? Okay. Medina tells Jones's life story about being like,

Barry Gordy of Motown's assistant and how he came up in Hollywood and how he, so his Benny Medina, who's J-Lo'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. It's Quincy's birthday. And, you know, a couple bottles later. and everything, and everybody's like, he's like, hey, 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 our city on. You know that man is over there?

And he's like, his name is Brandon Tartikov. We're going to do something. Just real quick. And he pulls out a script. And they, ding, me, me, me, me. And he makes Will Smith audition in front of like Oprah Spielberg. Like this start. At the party?

At the party. No. What are you talking about? And Will's like, yo, like, well, wait. like two weeks in... What a weird birthday party. And literally, Quincy Jones is like, the three men that can green light this deal right now

are in this room. Just read the script. Oprah, I think she read for the role of Aunt Viv. 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, he's like, so what do you think? What do you think?

It's like, yeah, let's do it. He's all right. wait philly you have a lawyer yet he's like well no and he calls it he's like bob newhart style he's like yeah what'd you really can you come by well how how far apart are they well it's triplets yeah man i've heard that situation it's not going to happen to another two hours yeah just come by real quick so how far apart aren't that he comes he literally the lawyer leaves the hospital where his wife is about to give birth and introduces him

to his new client, still his lawyer to this day. It says Philly meets 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? And for me there have been plenty of times. where I've had that moment and kind of squashed it or said no. Interesting. All in the name of, because again, I think the human experience is we'd rather be liked

than shine. Sure. And so, so yes, I will say that I believe that tortoise and the hair journey is the best journey. Yeah. but part of me does wonder what if you did take that audition? Yeah, yeah. What if you did that?

Yeah. Like, I didn't want to do SummerSoul. Like, I... Interesting. It took seven months for them to finally, like, talk me into doing that. I didn't want to do it. Wow.

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. So in that way, you're like the Gillian Jacobs character in the movie. That's why I obsessively watch.

that movie, Michael Biglia. Yes, exactly. But to the point of you being like the Gilling character, which is someone who's true to yourself and authentic and uncompromising to a degree, I guess my question is...

You still say that. I still disagree. But go ahead. Okay. But my question is, 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 going to go all in on this. What is that journey? Because that's, I think, something people struggle with all the time. 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-sabotized. There's a moment where I realized, wait, is that me too?

It's easy to do this. Yes. 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, hide behind Jimmy. Yeah.

Mammoth text and post on Instagram, writing books. Yes. With the exception. I love those posts. With the exception of me teaching at NYU, the first time I, we have a friend, Seth Herzog. Yeah. 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. It'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? And that's things I didn't think of. Like, I just thought, like, I'm going to teach.

Yeah, the day to day of it. All 30 of them will be receptive and open. No one's going to 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 high.

hiding in plain sight. Yeah. And so, you know, you just, I had to make a decision probably late 2017, early 2018, where I, 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 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-da. And, you know, so I had to let that go. But it's an everyday battle almost. Like, it's an everyday battle, like just waking up every day. And, you know, I have to, I do a morning routine where the second I get up, I spend 20 minutes, literally, like, my version of Eminem's opening scene in eight mile where you just got to, like, look in the mirror and talk to yourself and all that shit.

So, yeah, I do it. What's the best piece of advice someone's giving you that you used? 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 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 yeah like how did you get it i love that whole thing um i show up yeah yeah 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 six person. But you just have to show up. Yeah, that's right. I don't think it's talent or... I think I do that as a psychological insurance plan. Yeah. Like, okay, well...

Because it's so easy to not show up. It's so much easier to not show up. But again, 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 immense of musical intelligence or, well, he has so many records and he studies music and he knows all these obscure records and da-da-da-da-da-da-da. None of that helps. Like, none of that helps, especially what I'm doing now.

Like, there's no training for what I'm doing. I'm literally learning every day the art of storytelling and putting, even though I had the experience of making records. records, it's making movies is an entire, telling stories is entirely different medium. And so you just have to show up. So the final thing we do is working out for a cause. Is there a nonprofit that you like to support? And we will contribute to them and then link to them in the show notes.

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

Right. but the opposite happened and now a lot of our students are discovering their their culinary passion and yeah they attend the food and finance business school which is essentially the food version of the fame school wow yeah 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 thank you i appreciate it ameer it's been an honor. Thank you for having me, man. 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. I'm a fan of the show and I'm glad to be on. Thank you,

sir. Thank you, Phil. 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 Questlova on Instagram at Quest. At Quest. Love. You can check out his documentaries on S&L Music, on Peacock, or Sly Stone, on Hulu or Disney Plus. I highly recommend them. You can watch the full video of this episode on our YouTube channel. My YouTube channel is Mike Barbiglia. Check that out and subscribe. We are posting more and more videos. Check outberbiggs.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 are myself along with Peter Salomon, Joseph Barbiglia, and Mabel Lewis, associate producer, Gary Simons.

Sound Mixed by Kate Balinski. 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 for 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 four. 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, you go, hey, I know this podcast where Mike Barbiglia 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 out. We'll see you next time.