Mike Birbiglia's Working It Out - 166. Questlove: The Art of Self-Sabotage

Episode Date: April 14, 2025

This week 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

Um, who are you jealous of? Oh, God. Do I have to give a proper noun? I don't know. Uh, yeah. Do I have to give... 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 Questlove, AKA Amir Thompson. I was so, so thrilled to talk to Questlove for the podcast. We've been talking about this for years and years and years. I met him many years ago. He's the band leader at The Tonight Show with Jimmy Fallon. I got to know him even better when my movie Don't Think Twice came out about nine years ago. We just had a lot of long conversations about the themes of that movie and jealousy and groups of artists and that kind of thing. We both are huge, huge film fans. I'm a huge fan of the documentaries

he's directed, Summer of Soul, which he won an Academy Award for. We talk about today. He has two new films. One is called Ladies and Gentlemen, 50 Years of SNL Music, which is awesome. It's on Peacock. As well as Sly Lives about Sly and the Family Stone in parentheses, aka the burden of Black Genius, which you can catch on Hulu or Disney Plus. All of those movies. Summer of Soul, 50 Years of SNL Music, Sly Lives. Fantastic movies. Just fantastic. We had a great conversation today. Huge announcement came last week. My new show, The Good Life, which we filmed at the Beacon Theater in New York City, will debut on Netflix May 26th.

Memorial Day weekend. It's the Monday. I am so happy about how this turned out. We're editing it right now. It looks fantastic. I can't wait to share it with you. Check that out on Netflix May 26th. I have a couple shows coming up this summer. I am supporting John Mulaney along with my friends Nick Kroll and Fred Armisen in Portland, Maine at the Cross Insurance Arena, as well as August 10th at Garrison Grounds in Halifax. And finally, September 13th at Stanley Park in Vancouver. You can get tickets for all of those on birdbigs.com. Love this chat with Questlove. We talk about his documentaries, we talk about his music, we talk about his master class on DJing, which is another thing he made that I

love. Couldn't recommend more highly. He's an endlessly creative person. He wrote a great book on creativity called Creative Quest. Questlove is funny, he is insightful, he is just a brilliant creator. Enjoy my conversation with the great Questlove. Ooh, ooh, workin' it. I think with comedy, you don't have the same relationship with mistakes that musicians do. Yeah.

Whereas, you know, playing like an amateur, playing, people say something wrong when I play it right. Like, 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, I have a headache,

you know, like that sort of thing, so. That's great. It's funny because in the SNL documentary that you made, 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. People say music and comedy, there's an interrelationship all the time, but timing, all those things are crucial. 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 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.

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 then, and this all ties in together. Cause 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, when you did my podcast, like 10 years ago, this is a slow turnaround. Yeah, my stuff's supreme. 10 years ago. This is a slow turnaround. 10 years later. Yeah, yeah. 10 years later. That's right. 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 just mess around when you're of college age or whatever, and then I guess you start to think seriously maybe 26, 27. 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.

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 the thing is is that I believe that most people self-sabotage,

because we wanna control, we wanna know what's next. You wanna know what the next step is. Solid ground or is this quicksand. And not having the comfort or the know-how of knowing if you're going to drown or not, makes people just say, okay, nope, nope, this is where I get off, this is where I'm going to stay. This is my orientation. 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, Sigh in the Family Stone documentary, Sigh Lives,

the person who I think is in some ways the hero in addition to the director is Andre 3000. Cause 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 the Jedi mind trick people. We had the Jedi mind trick people.

The life of a documentary 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 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. Right. So you interviewed a bunch, some people like D'Angelo and others who have similar self-defeating tendencies. Yeah, I joke that there's the exact moment where D'Angelo recognizes he's not there to talk about like harmony structure and... That's so sweet. And he takes a drag of a cigarette and I know that stare that when he gives me that stare,

like I knew this was a trap. I knew this was a trap. But I had to... It was a very slow walk of trust, but 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? And some... How many people didn't show up?

We got stood up maybe three times. Oh, that's not bad. But yeah, there were, I will say that Andre was probably, when I asked him, he was just like elated. Like, finally, 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, so with Sly, do you know if he's seen it?

Yeah, he's seen it. Absolutely. Do you know if he likes it? Yeah, 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, yeah.

supposed to be the executive producer, or half say in it. But it's kind of weird because in this specific case, with the music copyright and all those things, the Jackson estate owns the Sly songs. Oh, well, Michael. They do? So 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 those things? And McCartney says, publishing, buy publishing. That's crazy. But you're supposed to buy like some songs.

Mike's just like, oh, I'll buy the entire house. Right. Yeah, so in 83. Yeah, in 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 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 he had to give a thumbs up in order for the music to be cleared. But we kind of came in at the top clear with what our intention was. Was basically to show people kind of what artists go through, but in a way that it didn't feel like

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. For me, it was important to show it in a way that didn't wreak of all, poor baby. Really just explain to you what the level of vulnerability that it takes to be that person. I mean, your personal story is not that dissimilar from Sly in the sense that you're both musicians, you're both DJs. Yes.

I mean, 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- 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 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? Yeah.

Okay, so in my mind, my thing is, how am I going to connect Benny Goodman and Kendrick Lamar? Exactly, and by the way, if people haven't seen this, they should watch your master class on DJing. I totally forgot I had that. I mean, it opened my mind to even the art of what DJing is. 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 mid-set to say, excuse me, excuse me, excuse me, hey, could you tell the chicken cross the road joke? Can you do that one?

Can you tell the chicken cross the road joke? Yeah, yeah, yeah. You're like right to get to the punch line 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 that?

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, The Temptations and even like, you know, The Temptations, and even like, Dyke and the Blazers, Funky Broadway. You know what I mean? 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, what you're not supposed to do, 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. 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, 91, don't know, don't know, don't know, don't know, don't know, don't know,

don't know, don't know, don't know, don't know, think about Robin Williams acts like 12 characters that once, don't know, don't know, don't know, don't know, don't know, don't know, yeah, man, that day, man, that day, like that was sly. He would make his own commercials up for products that- Don't exist.

Yeah, or like, let me do a commercial for products that don't exist. Yeah, or, you know, like, let me do a commercial for Tidybo. Like, and literally he would make his own commercials. So even then, what will happen is those nine, 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.

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

I was like, what? Yeah, so basically- It's like 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 and the Family Stone. Yeah. And so, yeah, it would seem rather up his alley, you know.

It was funny because 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 seeing how many of the songs, because you sent it as like a 45 minute file,

how many- Are 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, Oh! 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,

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 Michael and the Gang. So since- For real? Like that was his job? Well, yeah. So my dad was an oldies duet singer in the 50s

on chess records like back in the 50s. Wow. By the time I was born, the first wave of nostalgia culture kicks in. But also, my parents did not believe in babysitting. So you had to be on the job always. Literally, and it was normal. So you were thrust into professional music when you were a kid.

Yeah, and I would ask them all the time, was it normal for a five-year-old to be in a nightclub? Or when you hear like Brooke 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 in until like the late 80s. Yeah.

You know, with like doing the Jim and Tammy Faye Baker, like the, you know, the Clutching of the Pearls outrage, you know, with like doing the Jim and Tammy Faye Baker, like the, you know, the clushing of the pearls outrage, but no one cared. So yeah, I was a five, six, seven, eight, nine, 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 gonna be a very short window between like 72 to 76 maybe. And then he realized that was gonna 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. So as a result, my dad's like, okay, I gotta get off the oldie circuit and get in the nightclub circuit. Now, if you wanna go out for a night of dancing, you'll ask, oh, who's DJing? And you go to the club and see them DJing.

But in the mid 70s to mid 80s, bands were still pretty much part of nightclub culture. So 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 mall, I'll take that, that, that, that, that, that, that, that, and you know, it'd be like $400. We'll take home boxes of records.

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. KC and the Sunshine albums, whatever the hit was. Okay, The Hustle. Oh my gosh. KC 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? I always say this. So, okay. So Van McCoy had a very big hit in the seventies 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 can take the trash. So I would, whatever the flop was in that artist catalog, that will 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, 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- Songs 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, hey, ah. Yeah, something that people know. 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 minutes sequence in the SNL documentary is a DJ exercise, right? It is. Just to talk people through it in like lay person'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 basically a DJing of some of the best musical performances in the history of SNL. And what, as a lay... And make them collaborate together and sing and..., and what as a lay person. 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? Okay, so what's behind us, and can your viewers see your board over here? 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. So it's like cards on a board, this song, this song, this song. Cards on the board, like CSI style. Yes. Like whenever I hear a song, the first thing I say to myself is,

what key is this in? How many BPMs? Okay. It's like an obsession. I'll pull out my iPhone, go to my BPM counter. How many beats per minute? Right. So I'm like, okay, well, this song is 103 BPMs, and it's in E minor, and if there's a bridge to it. Yeah. 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. But when they go to walk this way, talk this way, 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. 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 six minutes of anything I've ever seen. And then no one sees Hanson coming at all. Oh, Hanson's great. 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, Oombop 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 when 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 hard to do that. But yeah, for me I want it to just,

I mean SNL is only good as it's cold open. And you need a powerful cold open before you tell a story. So I figure that's the best way to tell a cold open. ["Snowfall"] And I'm going to be a little bit more serious. I'm going to be a little bit more serious. I'm going to be a little bit more serious. I'm going to be a little bit more serious. I'm going to be a little bit more serious. I'm going to be a little bit more serious. I'm going to be a little bit more serious.

I'm going to be a little bit more serious. I'm going to be a little bit more serious. I'm going to be a little bit more serious. I'm going to be a little bit more serious. I'm going to be a little bit more serious. I'm going to be a little bit more serious. I'm going to be a little bit more serious. My category was the slap. So after Will Smith slaps Chris, they are now... That was my category. The Academy Award goes to Questlove.

The thing 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'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. 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.

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 at one point I told Jared, my manager, he asked the Disney people to pull us out of, you know, can we pull out of these things because, you know, the thing is too much. I don't want people to not like us because-

Yeah, it's the sly in you talking. Yeah, like I wanted it to stop. The self-saboteur. 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 Sundance a year before. Wow. 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 is like three rows up from you and, you know, are you in the same level as him? 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? Because at that time, it could happen to you too, like, oh, Mr. Hollywood. And then I'm sure you have that one person that doesn't know how to act now that you're in this phase of your life. 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 gonna be the same, never gonna be the same, never gonna, fucking, never gonna be, I was like, wait, are they allowed to be the same, never going to be the same, never fucking, never going to be. I was like, wait, are they allowed to curse on TV, mom? When I heard the word fucking, 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 is 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 not deserve this?

Is everyone happy for me? And the way that people are clapping was more like sin for help, because they're- Right, they're experiencing the drama of the slap that just happened that you barely even clocked. Exactly, and there was one point when I looked at- That's crazy. I looked at the Williams sister.

Like, I don't know if my mind, I was expecting like the ticker tape, he's the fellow thing, like where people stand up and you know, like the hero's walk. But definitely people were like clapping like this, which only to me was registering like... Like it's about you. And definitely people were clapping like this, which only to me was registering like, this is my worst nightmare. No one's happy for me. Yeah, all of your anxiety of 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 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 Chris. He's like, fuck no. Oh my God. And that moment. Oh my gosh. I 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, my thing was never about like, your moment got taken away from you. Or that was your glory moment, you know. Because actually, at the time 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 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 this is how I learned the term. You can manifest something, you can manafuck something. So she's like, you got your manafuckish. 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, that you would eventually let out and share. So now I really got to ask you, I was waiting for you to open the door. Cause I still watch it obsessively. 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 wasn't one for one with SNL. Like I wasn't even close to SNL. Like 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 of the DC Improv, and 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 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. So when you first start, your first job is, so any person working 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 at the DCM. First person I ever opened for actually was Chappelle. Really? 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 had to be almost like an experienced? Yeah. Really? Yeah, it was be almost like an experienced? Yeah. Really? Yeah, it was bizarre. It was just about, it was when Half Baked was just about to come out. 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 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 hadn't 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. That's so funny. I would say the highlight of my social celebrity standing, like Amir, he's so funny. Like literally. Amir's so funny.

I knew that whatever those guys were going to shoot wasn't going to be half as funny 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 slow-rounded 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. Do I have to give? The follow up question is who are you jealous of that you thought of but you didn't say? You know, I'll tell you that the kind of boohoo 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? Yeah. You know, when our, cause the thing was we were critically acclaimed, but critically acclaimed doesn't necessarily mean that we're hit makers. Right, you're beloved. Yeah, and kind of in the rap game,

you have to be a hit 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 artists. 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 don't care about that shit. That's so good. So, I will generally say that, yeah, in 96, when the Fujis are having their moment, you know, I might've sat in a bathtub like fully clothed,

like looking at their Rolling Stone cover with my darts, like, you know, and then, I mean, it happens with every cycle. Like there'd be moments where I, and I absolutely love the Fuji's. Like we had some of the best times touring and all those things. But at the point when they're like selling 12 million

and 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 the outcastcasts like nope. Hang on. Hang on. Oh my god. Oh my god. So yeah, I always felt like Back then I felt 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 was absolutely positively the best storybook ending ever. 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. 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 like, yeah, I want to be a star. Famous and so, 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 exchange for giving yourself to your work. I sat, so I sat there in the audience.

I saw your show, The Beacon, and The Beacon is, 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 he... 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 happen 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 hare 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, the story of how he jumps from the Fresh Prince to the Fresh Prince of Bel Air, going 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. Oh, really? Right, so the quickest story is that he, 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 Yo-MTV raps. Anything on Yo-MTV raps between 88 and 90 is just, it's now reaching middle America and everything. 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.

Okay. Medina tells Jones's life story about being like a Barry Gordy of Motown's assistant and how he came up 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' birthday and it's Quincy Jones' birthday. This is a crazy story. It's Quincy's birthday and a couple bottles later and everything and everybody's like, hey, Philly, come over here. Just calling him Philly, not even like Will. He says, I saw what you did on a couple bottles later and everything, and everybody's like, he's like, hey, Philly, come over here.

Just call him Philly, not even like Will. He says, you know, I saw what you did on Arsenio, and then da-da-da-da-da-da. You know that man is over there? And 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, dee-dee-dee-dee-dee-dee-dee,

and he makes Will Smith audition in front of like, Oprah Spielberg, like, this is starting. At the party? At the party. No. And. What are you talking about? And Will's like, yo, like, well wait,

I need 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 and he'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 him, here'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 till another two hours. Yeah, just come by real quick. And so... How far apart are they?

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 with a 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. Interesting. 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 experiences, we'd rather be liked than shine. Sure.

And so, yes, I will say that I believe the tortoise and the hare Journey is the best journey. But part of me does wonder, what if you did take that audition? What if you did that? I didn't want to do Summer Soul. It took seven months for them to finally talk me into doing that.

I didn't want to do it. Wow, why would I want to do that? I can't doing that. I don'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 watched that movie, Michael Biglia.

Yes, exactly. 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- You still say that, I still disagree, but go ahead. 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. I stopped kicking and screaming. I'll say that around like 2018, 2019 is when I started realizing, well, one thing is 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. Yes, yes. Point fingers and see they're always messing up. They're always messing up. And I didn't realize that for myself. And 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, 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. He's like, so what are you going to do if someone pulls out their phone or something?? 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 someone that talks too much, da da da da? And that's things I didn't think of. I just thought like, I'm going to go in and teach. Yeah, the day to day of it. All 30 of them will be receptive and open

and 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. 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. And so, 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, 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 gonna make fun of you because you went to da-da-da-da-da, 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 second I get up, I spend 20 minutes, literally like my version of Eminem's opening scene in Eight Mile where you just gotta 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 given 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 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? Like, how did you get in? I love that whole thing. I show up. Yeah, yeah. Which I know that doesn't sound like sage of ice 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. 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 mince of musical intelligence, or well, he has so many records and he studies music I know I give the impression that it's like, oh, it's supposed to be about this mince of musical intelligence or well, he has so many records and he studies music and that he knows all these obscure records and da da da da da da.

None of that helps. Like none of that helps, especially what I'm doing now. Like there was no training for what I'm doing. I'm literally learning every day, the art of storytelling even though I have the experience of making records, making movies is an entire, telling stories is a totally different medium. And so you just have to show up.

["The Last Supper"] So the final thing we do is working out for a cause. Is there a nonprofit that you'd 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. It's a passion of theirs. When it first opened, it was more like, well, these students are the lowest testing score

of all of 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. 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. 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. Amir, it's been as well. Thank you. I appreciate it. Amir, 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 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 one.

Thank you, sir. Thanks, dog. Working it out, cause it's not done. Working it out, cause there's no... That's gonna do it for another episode of Working It Out. You can follow Questlove on Instagram, at Questlove. You can check out his documentaries on SNL 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 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 are 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 Bleacher's Further 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 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 who 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 Berbiglia 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.