Questlove: The Art of Self-Sabotage

Interactive Transcript

spk_0 Who are you jealous of?

spk_0 Oh God.

spk_0 Do I have to give a proper noun?

spk_0 I don't know.

spk_0 I know.

spk_0 The follow-up question is who are you jealous of

spk_0 that you thought of but you didn't say?

spk_0 Yeah.

spk_0 That is the voice of the great.

spk_0 A mere Thompson, AKA Questlove.

spk_0 One of my all-time favorite episodes,

spk_0 we are re-airing this from April.

spk_0 It's a great conversation about creativity.

spk_0 I found it super inspiring and so did our listeners,

spk_0 which is why we are re-airing it today

spk_0 in case people miss it the first time

spk_0 or want to recommend it to friends.

spk_0 You can see Questlove in spinal tap 2,

spk_0 which is in theaters now.

spk_0 What a sentence.

spk_0 He has had an amazing year.

spk_0 He was nominated for an Emmy for his documentary,

spk_0 Sly Lives, who's nominated for the SNL Music Documentary,

spk_0 which is unbelievably good.

spk_0 I mean, actually, the Sly one is unbelievably good too.

spk_0 I mean, these are great, great pieces to watch.

spk_0 So a lot of stuff you haven't caught up on Questlove stuff,

spk_0 watch all of that this week.

spk_0 Special announcement we have launched.

spk_0 Working it out premium, this is an ad-free version

spk_0 of the podcast, which is always available.

spk_0 Almost 190 episodes available on Apple Podcast.

spk_0 And when you subscribe to working it out premium,

spk_0 you get three things.

spk_0 You get ad-free version of the podcast,

spk_0 no ads, you support the show, which means a lot to us.

spk_0 And number three, bonus content.

spk_0 This week we are releasing our first ever bonus content episode

spk_0 where I tag people's jokes.

spk_0 People sending their jokes last week on Instagram.

spk_0 This is in voice memos.

spk_0 It's really funny.

spk_0 It's really, really, really good jokes.

spk_0 But we have a great talk with Questlove today.

spk_0 Massive fan of Questlove.

spk_0 We talk about his music and documentaries about SNL

spk_0 and Slice Stone, enjoy my conversation with the great Questlove.

spk_0 I think with comedy, you don't have the same relationship

spk_0 with the mistakes that musicians do.

spk_0 Yeah.

spk_0 Whereas, you know, playing like an amateur,

spk_0 playing people say something wrong when I play it right.

spk_0 Like, there's roots,

spk_0 roots guys know I'm mad when I play everything correct.

spk_0 That's great.

spk_0 Like, what's wrong with you?

spk_0 Right.

spk_0 I don't know.

spk_0 It's a headache, you know, like that sort of thing.

spk_0 So that's great.

spk_0 That's funny because in the SNL documentary that you made,

spk_0 it's like, it was one of the best explanations

spk_0 of the relationship between music and comedy I've ever seen.

spk_0 That it's like the rhythm, the cadence,

spk_0 the timing, all those things are crucial.

spk_0 People say music and comedy,

spk_0 there's an interrelationship all the time, but you nailed it.

spk_0 I learned that it all came together

spk_0 probably in the first year of,

spk_0 and I never say like my life won family

spk_0 or the tonight show or whatever.

spk_0 Like, I consider where I go,

spk_0 like I'm in my senior college year of 30 Rock University.

spk_0 Right.

spk_0 And, you know, and I absolutely believe

spk_0 be you page intern or learn himself in all spots in between.

spk_0 There's like, if you don't go there,

spk_0 if you don't walk away,

spk_0 at least knowing four things that you didn't know before

spk_0 then you're kind of doing it wrong.

spk_0 So being in the building, you think was that first,

spk_0 created the first epiphany about that?

spk_0 That was the first green light I had.

spk_0 And then, and this all ties in together.

spk_0 Cause even with, you know, like with us really connecting,

spk_0 me watching, don't think twice.

spk_0 And just the entire relationship with rejection

spk_0 and self-sabotage, like that played a big role

spk_0 in the Sly Livs doc.

spk_0 Yeah.

spk_0 Like, but you were the first to chill it to me

spk_0 in a way that, and I still believe

spk_0 when we had a conversation about it,

spk_0 you weren't too certain if self-sabotage was a play in it.

spk_0 Okay, so to give everyone context.

spk_0 Yeah.

spk_0 When you did my podcast, like 10 years ago.

spk_0 Yeah, that's right.

spk_0 Oh, this is a slow turnaround.

spk_0 Yeah, like 10 years of premium, yeah, yeah.

spk_0 10 years later.

spk_0 That's right.

spk_0 Right.

spk_0 So when you, my theory was that when I saw,

spk_0 when I, when I, when I saw the, the film,

spk_0 I told everyone who was like inching 30 whatever.

spk_0 Like this is a must watch.

spk_0 Like if you want to know what the direction of your life is,

spk_0 cause you know, you just mess around

spk_0 when you're of college age or whatever.

spk_0 And then I guess you start to think seriously,

spk_0 maybe 26, 27.

spk_0 Yeah.

spk_0 But once you get to 31, that's almost like when your first

spk_0 mid-life crisis comes in because you don't know,

spk_0 if you're not doing exactly what you're on the path to doing,

spk_0 like you're still like hanging out messing around at 33, 34

spk_0 and then suddenly you start to panic.

spk_0 So I told everyone to watch that film.

spk_0 And my assessment was at least for a couple of the characters

spk_0 that they weren't aware that they were self-sabotaging.

spk_0 That's right.

spk_0 At large.

spk_0 So that's where we disagreed because you told me

spk_0 that you felt that they were fully aware

spk_0 that they knew what their limitations were

spk_0 and that they were comfortable.

spk_0 This is where we disagreed about my movie.

spk_0 Right.

spk_0 Cause the thing is that I believe that

spk_0 most people self-sabotage, you know,

spk_0 because we want to control, we want to know what's next.

spk_0 You want to know what the next step is.

spk_0 Right.

spk_0 Solid ground or is this, you know, a quick stand.

spk_0 And not having the comfort of the know-how

spk_0 of knowing if you're going to drown or not.

spk_0 Yeah.

spk_0 Makes people just say, okay, no, no, this is where I get off.

spk_0 This is where I'm going to say this is where I'm going to say.

spk_0 Right. So in other words, they're controlling their own

spk_0 kind of decline because they're afraid

spk_0 that maybe the incline isn't there.

spk_0 Yeah.

spk_0 I mean, declines are familiar.

spk_0 Letdowns are familiar.

spk_0 Disappointments are familiar.

spk_0 Yeah. As opposed to success.

spk_0 That's right.

spk_0 Like even success is scary.

spk_0 Like I can tell you firsthand that I'm probably the first person

spk_0 that would actually actively root against something good

spk_0 happening to him.

spk_0 Like I went through that period of like literally like,

spk_0 I can't take it anymore.

spk_0 Like make it stop.

spk_0 Like that sort of thing.

spk_0 So this is a so in your documentary,

spk_0 signed the Family Stone documentary, Si Lives,

spk_0 the person who I think is in some ways the hero in addition

spk_0 to the director is Andre 3000.

spk_0 Because he says this thing that is so deep,

spk_0 which is he's essentially describing what you're saying,

spk_0 which is like when you're at the level of success,

spk_0 that's lie in the Family Stone was at,

spk_0 you're giving to the world and taking from the world so much

spk_0 that when you stop, when one of those things stops,

spk_0 you actually don't know where to put that energy.

spk_0 Or where to get it from.

spk_0 With Andre making that realization in the film,

spk_0 first of all, he was probably the one interview subject

spk_0 that was totally abored and absolutely down for what I wanted

spk_0 to achieve.

spk_0 Oh, interesting.

spk_0 I kind of had to jet on mind trick people.

spk_0 We had to jet on mind trick life with a documentary filmmaker

spk_0 with the trick to semi trick people

spk_0 and making what you want to make.

spk_0 You can't exactly just come out and say,

spk_0 hey, you know like how there's similarities between this person

spk_0 I'm doing a doc or an in your current life right now,

spk_0 like your tendency to, you know, not show up at all,

spk_0 your tendency to keep people waiting for 12 hours,

spk_0 or your tendency to wait decades between records or your tendency.

spk_0 So you interviewed a bunch, some people like DeAngelo

spk_0 and others who have similar self-defeating tendencies.

spk_0 Yeah, I joke that there's the exact moment

spk_0 where DeAngelo recognizes he's not there to talk about

spk_0 like Harmony structure and,

spk_0 and,

spk_0 he takes a drag of a cigarette.

spk_0 And I know that steer that, when he gives me that steer,

spk_0 like,

spk_0 uh, yeah, yeah, yeah.

spk_0 I knew this was a trap.

spk_0 But I, you know, I had to, it was a very slow walk of trust,

spk_0 but you know, there was 19 other artists.

spk_0 Yeah.

spk_0 That flat out said no, or said yes.

spk_0 And seven hours later, you're on set like,

spk_0 are you coming or not?

spk_0 And so many people didn't show up.

spk_0 We got stood up maybe three times.

spk_0 Oh, that's not bad.

spk_0 But yeah, there were, I will say that André was probably,

spk_0 when I asked him, he was just like, elated like,

spk_0 finally, I have an outlet to let you guys know

spk_0 what I've been going through for the last 25 years.

spk_0 That's really interesting.

spk_0

spk_0 Yeah. So with Sly,

spk_0 do you know if he's seen it?

spk_0 Yeah, he's seen it.

spk_0 Absolutely.

spk_0 Do you know if he likes it?

spk_0 Yeah, he likes it.

spk_0 I know traditionally, especially with documentaries,

spk_0 the subject is not supposed to be the executive producer,

spk_0 or have say in it.

spk_0 Yeah, yeah.

spk_0 But it's kind of weird because

spk_0 in this specific case with the music copyright and all those things,

spk_0 you know, the Jackson estate owns the Sly songs.

spk_0 Oh, what did Michael do?

spk_0 So 1984,

spk_0 in 1984, no, no, it was the smartest business move,

spk_0 Michael Jackson ever made.

spk_0 I know he bought up a bunch of stuff, right?

spk_0 So he made a Beatles stuff.

spk_0 So ATV publishing was a publishing house.

spk_0 Weird enough, McCartney told him like,

spk_0 you know, Jackson's like, okay, so what are you doing with your money?

spk_0 Like, how do you grow it and all those things?

spk_0 And McCartney says, publishing, buy publishing.

spk_0 That's crazy.

spk_0 But, you know, you're supposed to buy like some songs.

spk_0 And Mike's just like,

spk_0 oh, I'll buy the entire house.

spk_0 Right.

spk_0 So in the 80s.

spk_0 Yeah, in 80s.

spk_0 83.

spk_0 He purchased ATV publishing, which is one of the biggest publishing houses.

spk_0 Like, it's Chuck Berry's songs, Sly songs, the Beatles songs,

spk_0 little Richard songs, that, and,

spk_0 you know, just in general,

spk_0 they, you know, they tell you from the gate that,

spk_0 you know, if you're doing any project on one of the artists in art that we

spk_0 hold copyright on, the first thing we're going to do is go to them to

spk_0 see if, you know, if this is something they approve of,

spk_0 or they like of, or whatever.

spk_0 So, yeah, so he had to give a thumbs up

spk_0 in order for the music to be cleared.

spk_0 But, you know, we kind of came in at the top

spk_0 clear with what our intention was.

spk_0 Was, was basically to show people

spk_0 kind of what artists go through.

spk_0 But in a way that he didn't feel like, you know, the world's tiniest violin.

spk_0 So, for me,

spk_0 it was important to

spk_0 show it in a way that

spk_0 didn't wreak of all poor baby.

spk_0 Yeah.

spk_0 Really just like, explain to you what

spk_0 the level of vulnerability that it takes to be that person.

spk_0 Do you, I mean, your personal story is not that dissimilar from Sly,

spk_0 in the sense that you're both musicians, you're both DJs.

spk_0 Yes.

spk_0 I mean, to give people who haven't seen the documentary,

spk_0 they should. It's incredible.

spk_0 It's like Sly was a Bay Area DJ.

spk_0 You know, that's the radio DJ.

spk_0 That's the one thing, when people asked me,

spk_0 what's the one thing that I learned about this that I didn't know?

spk_0 I knew he was a DJ, but I didn't realize

spk_0 the impact of that DJ, of him DJ.

spk_0 First of all, he starts DJing in 1961

spk_0 in the Bay Area.

spk_0 He's an open format DJ, which is the kind of DJing I do.

spk_0 Right. When I go to a gig, I don't know if you've been to a party where I've DJed before.

spk_0 Yeah. Okay.

spk_0 So, in my mind, my quite, my thing is,

spk_0 how am I going to connect Benny Goodman and Kendrick Lamont?

spk_0 Exactly. And by the way, if people haven't seen this,

spk_0 they should watch your master class on DJing.

spk_0 I totally forgot. I have a minute.

spk_0 It is, it opened my mind to even the art of what DJing is.

spk_0 Like, I didn't understand it before that documentary.

spk_0 Yeah. Movies and television, really, that's the one thing that

spk_0 irks me about how things are depicted.

spk_0 Because when I'm DJing, I'm just the equivalent of me just coming up to you,

spk_0 mid-set to say, excuse me, excuse me, excuse me, hey, could you tell the chicken crossed the road,

spk_0 yeah. Can you do that one? Can you tell the chicken crossed the road, too?

spk_0 Like, you're like, right, to get to the punchline and someone interrupts you like,

spk_0 hey, you know, I think I've been suggesting better than you.

spk_0 But they always do that on television.

spk_0 Like, the person goes up to the DJ like, hey, could you believe me?

spk_0 Yeah.

spk_0 So, yeah, basically, slides an open format DJ, which means that

spk_0 here he's going to play the Beatles and Bob Dylan, but he's also going to play like, you know,

spk_0 the temptations and even like, dyke in the blazers, funky Broadway, you know what I mean? Like,

spk_0 and that was sort of unheard of.

spk_0 Like, mixing rock and soul on the same radio station, like, that's not supposed to happen.

spk_0 So, yeah, what you're not supposed to do, he's, and so, you know, he's probably just as a human

spk_0 contrary to start with whatever he's not supposed to do you're doing.

spk_0 Yeah.

spk_0 So, I believe that and on top of that as a personality, if you're familiar with

spk_0 like Robin Williams's character and Good Morning Vietnam, like those, those morning shows,

spk_0 you DJs, 91, don't know, you know, think about like Robin Williams acts like 12 characters.

spk_0 Well, yeah, man, man, man, man, like that was like, he would,

spk_0 he would make his own commercials up for products that don't exist. Yeah, or, you know, like,

spk_0 let me do a commercial for tidie bow, like, right? And literally, he would make his own commercial.

spk_0 So, even then, what, what will happen is those 9, 10, 11, 12, 13 year olds in 1960 will now be

spk_0 the counterculture hippies in 67, 68, 69. So, kind of the, what you know as the Bay Area hippie or

spk_0 the counterculture person, like, Sligh had a major hand in raising them. Yeah. And so, I don't think

spk_0 that part's even known. And even more than that, like, with the bands, like, the first producer of

spk_0 The Great Full Dead, Sligh Stone, the first producer of Jefferson Airplane, Sligh Stone, like,

spk_0 yeah, he also, I couldn't believe it when I saw that he produced somebody to love.

spk_0 Yes, I was like, what? Yeah. So, Bay, one of the biggest rock hits of all time.

spk_0 Yeah. So, you know, he just, that, I didn't realize how much prep work he did five years before

spk_0 he officially came out as Sligh and the family stone. Yeah. And so, yeah, it would seem rather

spk_0 up his alley, you know. It was funny because when I did the Old Man in the Pool at Lincoln Center,

spk_0 I had just seen your masterclass on DJing. And I was like, oh my god, it would be such a dream

spk_0 if Questlove would be open to doing a pre-show set. And you, and I asked you, and you're so generous,

spk_0 and you did it. What was amazing about the experience was seeing how many of the songs, because you

spk_0 sent it as like a 45-minute file. How many? I was just going to feed you songs on your Spotify.

spk_0 Yeah. Yeah. Yeah. I'm thinking even that I could look up the songs. The song, a lot of the

spk_0 songs, a lot of the songs they don't even exist on Apple Music or Spotify. So, I'm like, what is your

spk_0 catalog? Where is your catalog? When you're making that, I mean, it was, like, in other words, it was

spk_0 things as different as something from Motown and then the cure. And then you would find how to match

spk_0 those two things. And then it would be a hip hop track and it would be a classical track. It would

spk_0 be a jazz track. And where, okay, where do those exist when you make those mixes?

spk_0 So, right about now, so I'm going to weird, I'm going to third phase of record collecting.

spk_0 So, I've been shopping with my dad, the kind of connecting thing that I have with my father,

spk_0 because he too was a musician. That was a nightclub artist that required songs to learn for whatever

spk_0 environment that he's in. Yeah. We got to learn Celebration by Cole in the game.

spk_0 So, since... For real? Like, yeah, that was his job? Well, yeah. So, my dad was an oldies-do-op singer

spk_0 in the 50s on chest records, like back in the 50s. Wow. By the time I was born, the first wave of

spk_0 nostalgia culture kicks in. But also, my parents did not believe in babysitting.

spk_0 Okay. So, you had to be on the job always. Literally, and it was normal.

spk_0 So, you were thrust into professional music when you were a kid?

spk_0 Yeah. So, I would ask them all the time. Was it normal for a five-year-old to be in a nightclub?

spk_0 Or when you hear, like, Brooksheel still stories of like, yeah, I was at Studio 54 when I was

spk_0 12 and 13. Scandal culture or outrage culture didn't really kick it into like the late 80s.

spk_0 Yeah. You know, with like doing the Jimmy and Tammy Faye Baker, like the, you know, the

spk_0 Clushing of the Pearls, Outrage, but no one cared. So, yeah, I was a five, six, seven, eight,

spk_0 nine, ten-year-old, either playing percussion on stage with my family. By the time I was 11,

spk_0 I could run the lights. Unbelievable. My sister and I would run the soundboard in the lights as,

spk_0 you know, as kids. So, the whole point is that my dad sort of stayed on in that circuit for maybe

spk_0 like three to four years between like 72 to 76 maybe. Yeah. And then he realized that was going

spk_0 to be a very short window because as time moves on by the late 70s, early 80s, then suddenly the early

spk_0 60s Motown, the Big Chill, Beatles Mania, you know, starts to kick it. Yeah. So, as a result, my dad's

spk_0 going to get off the oldie circuit and get in the nightclub circuit. Now, deep, you know, now if

spk_0 you want to go out for night of dancing, you'll ask, oh, who's DJing? And you go to the club and see

spk_0 them DJ. Yeah. But in the mid 70s, the, you know, mid 80s, bands were still pretty much part of

spk_0 nightclub culture. So, my dad started a nightclub back and I'll say twice a month we would go

spk_0 binge shopping. We're literally, we just go to the wall. I'll say that, that, that, that, that,

spk_0 that, that, that, that, that, that, that, you know, be like $400. We'll take home boxes of records.

spk_0 Yeah. And then my dad's band would rummage through the box of 45s and albums, whatever the hit was.

spk_0 Okay. The hustle. Oh my gosh. Casey and the Sunshine Band will take that. And whatever wasn't good,

spk_0 I, I want to get everything else. Yeah. So, I'm probably the first music expert that

spk_0 gravitated towards the flop song. What's the flop song? I always say this. So, okay. So,

spk_0 Van McCoy had a very big hit in the 70s with the hustle. But then his follow up song, changed with

spk_0 the times was a dud. So, of course, the band would take, we'll take the hustle 45 and learn this.

spk_0 And yeah, man, you can take the, the trash. So, right. I would, whatever the flop was in that

spk_0 artist catalog. Yeah. That will wind up in my record collection because the band didn't want it.

spk_0 Yeah. So, I just, when you're, when you're between one and 16, you're not cynical, you're not

spk_0 discerning. You just, you own a record. Yeah. Yeah. Sure. And so, I, I, it was a long time before I

spk_0 realized that a lot of my favorite songs growing up were flops. Yeah. And songs that people didn't

spk_0 like. So, but that people didn't like, but that kind of raised me now where like, I think it's

spk_0 Captain Obvious. Like, if I play a hit, it's because I know, okay, this checks pretty big. So,

spk_0 I better play some songs that people, right. They're paying you well. Yeah. You should, you should

spk_0 throw in Heya. Yeah. Something that people know. Yeah. Yeah. But yeah, I'm the guy that's always

spk_0 trying to trick you or figure out ways to trick you into a song that you didn't know was a dance

spk_0 able song. Well, the beginning of the first six minutes sequence in the SNL documentary is a DJ

spk_0 exercise, right? It is. Just to talk people through it in like lay person's terms. The first six

spk_0 minutes is, it's on peacock, it's streaming on peacock. Yeah. The first six minutes is almost like

spk_0 a short film unto itself on its own, right? Because it's it's it's it's a it's basically a DJing of

spk_0 some of the best musical performances in the history of SNL. And what as a as a, as a

spk_0 as a lay person, I'm just going, Oh my God, this song is related to that song. So, okay. So what's

spk_0 behind us and can can your viewer see your your the board? Your board over here. Yeah, they can sort

spk_0 it and they can't see the words. But like, yeah, right. But yeah, this is literally,

spk_0 I'll say it took 11 months to make that montage. Oh my gosh. Shout out to John McDonald also,

spk_0 like a master editor. It helps when your editor is also a musician. Yeah. So it's cards on a board.

spk_0 This song, this song, this song. It cards on the board like CSI style. Yeah. Like, like whenever I

spk_0 hear a song, the first thing I say to myself is, what keys this in? How many BPMs? Okay. It's like

spk_0 an obsession. I'll I'll pull out my iPhone, go my BPM. Many beats per man. Right. So I'm like, okay,

spk_0 well, this song is 103 BPMs and it's in E minor. And if there's a bridge to it. Yeah. Ah,

spk_0 like great example. Uh, figuring out, and this is John McDonald's, I can't take credit for that.

spk_0 Him knowing that the course of walk this way, uh, which is in C, which is different,

spk_0 the actual walk this way songs in E. Yeah. But when they go to walk this way, talk to that's

spk_0 in C minor. And somehow he figures out the two seconds that will connect walk this way to shares.

spk_0 I found someone. Yeah. And she just happens to say the words when you walked away. So that's

spk_0 even a double like as a key, they're, they're both married to each other. But as a subject,

spk_0 lyrically, they fit. Lyrically, it even fits. And so I mean, that's that's what took 11 months

spk_0 because we just wanted that sequence. This is as good as any six minutes of anything. I've ever

spk_0 seen. And then no one sees Hanson coming at all. Oh, Hanson's great. Right. And then honestly,

spk_0 you're watching it going, Hanson's pretty good. Yeah. Oh, you picked, you picked the right

spk_0 eight seconds to be like, let me actually do that. Like, well, the perfect example of D of the DJ

spk_0 song where you go, oh, my, it's pretty good. Well, yeah, as a DJ, I listened to songs

spk_0 as a DJ. It's been a long time since I listened to music for pleasure.

spk_0 No, it's also a hard thing to do. Like what happens with the thing that gave you pleasure? It

spk_0 becomes your job. Oh, man. And then you become numb to like, let me just put this on because I

spk_0 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

spk_0 to just, I mean, SNL's SNL is only good. It's as it's cold open. And you need a powerful cold

spk_0 open before you tell a story. That's right. I figure that's the best way to tell a cold open.

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spk_0 With summer of soul, this is like a tiny bit of trivia. You won the Oscar.

spk_0 I think after the slap.

spk_0 After my category was the slap.

spk_0 So after we'll Smith slash Chris, they that was my now. That was my cat.

spk_0 The candy award. But the thing is the thing is the thing is that you know when people were

spk_0 first asking me my reaction to it, I don't think they believed me when I was like I wasn't there.

spk_0 Like if you're up for anything in that level of importance, you're not in your right mind.

spk_0 What's so ever? What does it feel like? What was your headspace?

spk_0 Okay. So for starters, so it's a little weird when you know you're campaigning for a year. So

spk_0 you're seeing the same faces of the other doc people that you're up against. That's right. At 40 other,

spk_0 you know, there's the independent spirit awards and there's the, you know,

spk_0 it's the same group of people at all the award shows. Yeah. Yeah. And you know, it gets

spk_0 and we had a big year that year. So already I'm feeling like I'm the Grinch that stole awards.

spk_0 Yeah. Yeah. Yeah. So each one you'd want a lot of awards at that point. Yeah. Yeah.

spk_0 So I'm already just in a make it stop thing. I think like at one point I told

spk_0 Jared my manager like he asked the Disney people like the pull us out of, you know,

spk_0 like can we pull out of these things because you know, the thing is too much. Like I don't want

spk_0 people to not like us, you know, because it's the sly in you talking. Yeah. Like I wanted it to stop

spk_0 right. And so please don't let me win the Oscar. There was about maybe I'll say the first half hour

spk_0 just sitting there and all the anxiety of it all. And this is like the last part of the journey.

spk_0 Like we started with the sun sun, sun, sun dance year before. Wow. And that entire year of just

spk_0 going through that process and you're just sitting there and you're, you know, realizing that

spk_0 you're up against the person who's, you know, you're very first documentary you ever watched

spk_0 on TV is right is like three rows up from you and, you know, are you in the same

spk_0 level as him? Then you're thinking about all your relationships and who's going to like you,

spk_0 who's going to be your friend? Will you be in like you after this? Will your family like you

spk_0 after this? I'm thinking about, well, thanksgiving be normal. Oh my god. Because I, you know, at that time

spk_0 it's, it's, and you know, it could happen to you too. Like, you know, like, oh, Mr. Hollywood. And

spk_0 then I'm sure you have that warm person that doesn't know how to, to act now that you're in this

spk_0 phase of your life. Yeah. And so I think in my mind, I was just sitting there like frozen,

spk_0 totally channeling out what was happening because we're in the back row. And it's never going to

spk_0 be the same, never going to be the same. Never a fucking, never going to be, I was like, wait,

spk_0 are they allowed to curse on TV? When I heard the word fucking, oh my god, then I stopped. It was

spk_0 like, I looked at my mom like, wait, they're allowed to curse on television. Oh my god. That's

spk_0 weird. And then I just went back to, oh god, it's all going to be different. It's all going to be

spk_0 different. Summer's always all going to be different. And I stood up totally not registering what

spk_0 really happened because even then I just thought, man, that was a poorly executed sketch. Right?

spk_0 That's what I thought. I thought it was a bit. I thought it was a bit. Right. But when you're walking

spk_0 and you're walking slow, you're, you're already walking with this whole, did I deserve this?

spk_0 Did I not deserve this? Are the, is everyone happy for me? And the way that people are clapping

spk_0 was more like sin for help because they're, they're experiencing the drama of the slap that just

spk_0 happened. Right. You barely even clocked. Exactly. And there was one point when I looked at the

spk_0 that's crazy. I looked at the Williams sister. Like, I don't know if my mind, I don't know if my

spk_0 mind, my mind, I was expecting like the, you know, the tip, ticker tape, he's a jolly gofellow thing.

spk_0 Like where people stand up and, you know, like, you know, like that, like the heroes walk. Yeah.

spk_0 But definitely people were like clapping like this, which only to me was registering like,

spk_0 like it's about you. This is my worst nightmare. Yeah. I'm excited. Are people going to like me

spk_0 anymore? And then people are confusedly clapping about something that had nothing to do with you.

spk_0 And you don't even fully clock what just happened. Yeah. I didn't clock what happened. And

spk_0 then I get to the front and there was kind of a moment where I knew my back was to the audiences,

spk_0 to the cameras. And I knew I had about a good three seconds to ask him. I said, was that a sketch?

spk_0 Was that real? To Chris. He's like, oh my god. And that moment, oh my gosh, I turned around and

spk_0 realized, oh my gosh. Oh god. That was real. And it was never, and it was never, my thing was never

spk_0 about like your moment got taken away from you. That was a glory moment, you know, because

spk_0 actually at the time my ex told me she said, congratulations. You got exactly what you want.

spk_0 So I'm thinking in terms of like, oh, you mean the Oscars? No. He's like this whole process

spk_0 watching you this entire year of you scared of your own shadow. Like you told the universe,

spk_0 yes, I would like to win it, but I would want to win it in the most quietest way possible.

spk_0 On your own terms. So that's this is how I learned the term. You can manifest something. You can

spk_0 you wanted to win this Oscar in the quietest way possible where nobody's going to judge you or

spk_0 be angry with you. And you asked the universe to make it happen. And that's exactly what happened.

spk_0 That's really interesting because it's like my my experience of writing don't think twice. A lot

spk_0 of it was it actually cured me of jealousy because what I realized about jealousy is if you want

spk_0 something that someone else has, you can't just one for one have what they have and be you at the

spk_0 same time. See, I knew that you would eventually let out and share. So now I've really got to ask you

spk_0 I was waiting for you to open the door because I still watch it obsessively. Like so

spk_0 was that did at one point you tried to fit into the 30 rock ecosystem either as a writer or

spk_0 to some degree. Yeah, yeah, how hard is it to get in that system? Oh, I feel like a nipple baby. That was

spk_0 just ushered in because no, I I wasn't one for one with SNL. Like I I wasn't even close to SNL.

spk_0 Like they like I they didn't even I didn't even audition. So the whole acting out of people auditioning.

spk_0 But the part that I relate to is that when I was coming up, I moved to New York in 2000 and I'd

spk_0 been working the door of the DC improv and I all of a sudden the people who were getting heat all

spk_0 around me were like, I was like, wait, but I'm funny. These people and then people blown up. People

spk_0 again, SNL people are getting the daily. She'll all this shit. And it's like and it's a weird

spk_0 experience to feel that. So when you first start your first job is so any person working the door

spk_0 yeah or any person like that's that's the entry that's the intern level of getting into that system.

spk_0 In some ways, yeah. Okay, the comedy club system I was working the door for like three years of

spk_0 the DC improv first person I've ever opened for actually was ship hell. Really? Okay. He was 24.

spk_0 I was 19. He was headlining comedy club nationwide. It was 24 years old. And is that unusual?

spk_0 Yeah, to be that almost unheard of. Really? So you have to be almost like an experienced. Yeah.

spk_0 It was yeah, it was a bizarre. It was just about what it was when Half-Bake was just about to come out.

spk_0 Funny script I've ever read in life. Side note. So all the music for season two of ship hell.

spk_0 That's when they hired me. Do you want to tell us what got me the tonight show? But yeah, I was the

spk_0 musical director of season two and very little season three that happened. And I got to tell you

spk_0 I had that Ricky James sketch. A good five months before it came out. Oh, you were what it

spk_0 seemed to do. Do you know how crazy my life was? Where I would actively I would go to parties. Yeah.

spk_0 And have that script in my bag. Oh my god. And I would perform it for people as a one-man show.

spk_0 That's so funny. The I would say the highlight of my social celebrity standing. Yeah. Like a

spk_0 mirror. He's so funny. Like literally. I'm here so funny. No. I knew that whatever those guys were

spk_0 going to shoot wasn't going to be half as funny. Yes. As what I was doing at parties every night. And

spk_0 I perfected out. But I had my own things to it. Like memorized it. Like, yeah, you know, I went to

spk_0 the ship hell show. We're doing this thing about, you know, Rick James, like, you know, and his

spk_0 is arguments with Charlie Murphy. And oh, wait, I think I'm going to be here.

spk_0 Then I start reading it. Imagine.

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spk_0 it out comes from RULA. Look, finding a therapist is hard. Just ask me. I've had two therapists

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spk_0 This is a slow round and actually fitting from what we were talking about. Who are you jealous of?

spk_0 Oh God. Do I have to give a proper noun?

spk_0 I don't know.

spk_0 The follow-up question is who are you jealous of that you thought of but you didn't say?

spk_0 I'll tell you that the kind of boo-hoo, woe is me positioning that I took with the roots.

spk_0 When it came time to like, is this going to be our turn? Is this going to be our moment?

spk_0 You know, because the thing was we were critically acclaimed but critically claim doesn't

spk_0 necessarily mean that we're hip-makers. And you're beloved.

spk_0 Yeah. And kind of in the rap game, you have to be a hip-maker.

spk_0 So we totally, I will say that I'm proud to say that a lot of our surviving was just being

spk_0 prestige artists. But it was almost at the point that people thought we wanted to be

spk_0 prestige artists where they were just three like, well, you guys don't care about like hit singles

spk_0 and going platinum and everything. And then inside my voice, I'm like, what the fuck? I knew

spk_0 care about that shit. That's so good. So, you know, I will generally say that, yeah, in 96

spk_0 when the Fuji's are having their moment. Oh, yeah. You know, huge. I might have sat in a bathtub like

spk_0 fully clothed like looking at their rolling stone cover with my darts. You know, and then

spk_0 and then it happens with every cycle. Like, there be moments where I, you know, and I absolutely

spk_0 love the Fuji's. Like, we had some of the best times touring and all those things. But, you know,

spk_0 at the point where they're like selling 12 million and, you know, congrats guys. He just broke

spk_0 300,000 and it was just like, we're never going to make it. So there were moments with that. And then

spk_0 like, at 98 when I came out, like, okay, it's about us. And then the Alcats was like, nope, hang on,

spk_0 hang on. Oh my god. So yeah, I always felt like back then I felt like we were rude off the

spk_0 retinue's reindeer. Like, not allowed to play in reindeer games. I love that. But I will also tell you

spk_0 some 32 years and 17 albums later looking in the rear view mirror of what's happened to everyone.

spk_0 This, this was absolutely positively the best storybook ending ever. Like, I'll ask you, I don't

spk_0 know what the equivalent of asking you. Would you rather your second album sell 12 million units and

spk_0 you win a whole bunch of awards. And then you just have the craziest crash in Burn of All Time or

spk_0 would you rather tortoise in here your way. Even when you pass the finish line, you don't realize

spk_0 that you've made it. I thought I wanted the first one and I know now I wanted the second one,

spk_0 now that I've had the second one. Because when I was in my 20s, I was the, I was like, yeah,

spk_0 I want to be famous and you sell right? Yeah. And then now I'm 46. I'm just like, oh, this is great.

spk_0 I go to every city, people show up. They want to see what I'm doing. They don't want to see me

spk_0 because I'm known from something that isn't me. They like what I'm doing. And it's like, oh my

spk_0 God, that's the greatest gift. It's the people who listen to his podcast. It's the greatest gift

spk_0 you can possibly imagine in exchange for giving yourself to your work. I sat, so I sat there

spk_0 in the audience. I saw your show, the beacon. And the beacon is, you know, that's a big deal.

spk_0 Like I remember playing that when I was, you know, my dad played, I think I played the beacon

spk_0 when I was 12 with my dad. So I know my gosh, that's what dude, I was his band leader when he,

spk_0 you know, it's a big deal. I did when I was 12. Well, I don't count anything. I did Madison Square

spk_0 Garden. I don't count anything. I did Yankee Stadium. That's the team. It beacons a big deal.

spk_0 Anything with my dad, look, I just happened to be there. I just happened to be there. But,

spk_0 you know, I am, yeah, it is. And it's hard to, in hindsight, yes, the tortoise in the hair

spk_0 journey. Yeah. So you're happy with that version of it. I'm happy with it, but I also,

spk_0 you know what I am? I'm the person, okay, speaking of Will Smith, I'm the person that once asked

spk_0 Will Smith, like the story of how he jumps from the fresh prints to the fresh prints of Belair.

spk_0 Uh-huh. Going from the fresh prints to Will Smith was a move in which he didn't consult anybody.

spk_0 Like, right. So the, the quickest story is that he, you know, they had this incredible success with

spk_0 their second album. He did DJ. I'm the rapper. They sell millions of units. They're really just

spk_0 benefiting the, the, the, the, the, the water fall of, of, of UMTV wraps. Right. Anything on

spk_0 UMTV wraps between 88 and 90 is just, it's now reaching middle America. Yeah, sure. So they benefited

spk_0 from that. So when their next album comes out in this corner, which I actually love better,

spk_0 it flopped. But they still, you know, did the rounds of promotion and all those things. And they

spk_0 did the Arsenio Hall show. Yeah. And did a really compelling performance of, I think I can

spk_0 beat Mike Tyson. That was the first single from that thing. And Quincy Jones happens to watch it.

spk_0 And Quincy Jones rings up a super manager, Benny Bendinga. Who is the fresh prints of Belair?

spk_0 Okay. Madena tells Jones' life story about being like a Barry Gordy of Motowns assistant and

spk_0 how he came up in, in Hollywood and how he, so his, Benny Bendinga, whose Jalos manager is the

spk_0 fresh prints of Belair. So that's about his life. Oh, interesting. Right. So we'll Smith not knowing

spk_0 what he's getting called to come to Quincy's house for. He thinks he's going to Quincy Jones's

spk_0 birthday. And it's Quincy Jones's birthday. This is crazy story. It's Quincy's birthday. And

spk_0 you know, a couple bottles later and everything and everybody's like, he's, hey,

spk_0 Philly come over here. Just call him Philly. Not like, well, he's just, you know, I saw what

spk_0 you did on a city on and that, you know, that man is over there. And he's like, his name is a

spk_0 Brandon Tarticle. We're going to do something. It's just real quick. And he pulls out a script.

spk_0 And then he makes Will Smith audition in front of like Oprah Spielberg. Like this

spk_0 start at the party. At the party. No. And what are you talking about? And Will's like,

spk_0 yo, like, well, wait, I need like two weeks and what a weird birthday party.

spk_0 And literally Quincy Jones is like the three men that can green like this deal right now are in

spk_0 this room. Just read the script. Oprah, I think she wrote red for the role of Aunt Viv.

spk_0 I got like literally people are like his co-stars are like established actors and whatnot.

spk_0 And so he does it. And then he looks at everyone's like, so what do you think? What do you think?

spk_0 It's like, yeah, let's do it. Is that all right? Wait, Philly, you have a lawyer yet? He's like,

spk_0 well, no. And he calls him. He is like, Bob Newhart style. He's like, yeah, what'd you? Really?

spk_0 Keep coming by? Well, how far apart are they? Well, it's triplets.

spk_0 Yeah, man, I've heard that situation. It's not going to happen to another two hours.

spk_0 Yeah, just come by real quick. It's so far apart are they? He comes. He literally, the lawyer

spk_0 leaves the hospital where his wife is about to give birth and introduces him to his new client.

spk_0 Still his lawyer to this day. It says Philly meets your new lawyer and they drew up a contract.

spk_0 And so I was like, wait a minute. So you flew there thinking that you're going to a birthday party.

spk_0 How are you explaining to Jeff and your manager and everyone else what you just did?

spk_0 Yeah. And for me, there have been plenty of times where I've had that moment and kind of

spk_0 squashed it or said no. Interesting. All in the name of, because again, I think the human

spk_0 experiences we'd rather be liked than shine. Sure. And so, so yes, I will say that I believe that

spk_0 tourists in the hair journey is the best journey. Yeah. But part of me does wonder, what if you did

spk_0 take that audition? Yeah, yeah. What if you did that? Yeah. I don't want to do some or so.

spk_0 Like I'm interesting. It took seven months for them to finally like

spk_0 talk me into doing that. I don't want to do it. Wow. Why would I want to do that? I can't do that.

spk_0 I can't do that. And then you start talking yourself into if you say it, it happens. So in that

spk_0 way, you're like the Gillian Jacobs character in the movie. That's why I obsessively watched that

spk_0 movie might be big. Yes. Exactly. But the guilt, but to the point of you being like the

spk_0 Gillian character, which is someone who's true to yourself and authentic and uncompromising

spk_0 to a degree, I guess my question is you still say that I still disagree. Okay. But

spk_0 but my question is and because a lot of creatives listen to this show, they they had to convince you

spk_0 to do some of Seoul and end up being this huge triumph. How did you get from not wanting to do it

spk_0 to being like, no, I'm going to go all in on this. What is that journey?

spk_0 Because that's something people struggle with all the time. I stop kicking and screaming.

spk_0 I'll say that around like 2018, 2019 is when I started realizing one thing is watching people

spk_0 getting their own way, watching people self sabotage. There's a moment where I realized,

spk_0 wait, is that me too? It's easy to do this. Yes. Point fingers and see they're always messing up.

spk_0 They're always messing up. And I didn't realize that for myself. And you know, kind of one of my,

spk_0 I realized that I made a life being a second banana hiding behind a DJ rig, hiding behind a drum set,

spk_0 hiding behind to reek, hide behind Jimmy. Yeah.

spk_0 Mammoth text and post on Instagram writing books. Yes. With the exception. I love those, I love those

spk_0 posts. With the exception of me teaching at NYU. The first time I, we have a friend,

spk_0 Seth Herzog. And when I accepted teaching at NYU, he got in my head like three weeks before.

spk_0 Like, man, so you're about to be a professor at NYU. I was like, yeah, you know, it's like so,

spk_0 what are you going to do? Like someone pulls out their phone or something? And I was like, well,

spk_0 what do you mean? It's like, well, you're dealing with kids. Like, do you not a handle,

spk_0 you know, someone that talks too much and that's things I didn't think of. I just thought,

spk_0 like, I'm a go-and-teach and the day of day of it. All 30 of them will be receptive and open.

spk_0 No one's going to be disruptive or ask a bunch of questions or be a problem. And he got in my head

spk_0 about that. And I realized, oh, God, this is the first job I ever had in which I don't have a shield

spk_0 to do the dirty work for me. To recast the face, the audience and talk to them. Jimmy has to

spk_0 face the audience every night. So I realized there's a level of leadership vulnerability that I've

spk_0 been avoiding by hiding in plain sight. And so, you know, you just, I had to make a decision,

spk_0 probably late 2017, early 2018, where I, it wasn't serving me to hide in plain sight. And on top of that,

spk_0 where I think I wanted to go in life, I'm going to have to drop something in order to get it.

spk_0 And so I had to stop being the reluctant, you know, person, you know, the person too cool for school

spk_0 says no first before, I ain't doing that. That's dumb. You know, and I had to examine like,

spk_0 why do you think that's dumb? Because you think, well, you think the guys are going to make

spk_0 fun of you because you went to da da da da da. And, you know, so I had to let that go. But it's

spk_0 an everyday battle almost like, yeah, it's an everyday battle. Like just waking up every day. And,

spk_0 you know, I have to, I do a morning routine, yeah, where second I get up, I spend 20 minutes,

spk_0 literally like my version of, of Eminem's opening scene in eight mile where you just gotta,

spk_0 like look at the mirror and talk to yourself and watch it. So yeah, yeah, I do it.

spk_0 What's the best piece of advice someone's given you that you used?

spk_0 All right, if a person asks me like, or is wondering, because that's the thing, it's like, wait,

spk_0 where do you still doing here? I get a, that a lot because I don't have the same numbers on the

spk_0 boards as established people, especially in my, my field of hip hop. But I've spent 20 years of

spk_0 somehow getting that, oh, surprised you're here. Like, wait, you're here too. Yeah. Like, how did

spk_0 you get in? I love that whole thing. Um, I show up. Yeah, yeah. Which I know that doesn't sound like

spk_0 sage of ice or whatever. But if you look at the amount of people, like a lot of things I just show

spk_0 up for is because someone else didn't show up for it. And I know I'm the fifth person or the sixth person.

spk_0 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

spk_0 psychological insurance plan. Yeah. Like, okay, well, it's so easy to not show up. It's so much

spk_0 easier to not show up. But again, I tell people from the mountaintops, like, I know I give the impression

spk_0 that it's like, oh, it's supposed to be about this, this, mental musical intelligence or well,

spk_0 yeah, so many records and he studies music and that I, he knows all these obscure records and

spk_0 that. None of that helps. Like, none of that helps, especially what I'm doing now. Like, there was

spk_0 no training for what I'm doing. I'm literally learning every day, the art of storytelling and

spk_0 putting, even though I have the experience of making records, it's making movies is an entire

spk_0 telling stories is a tally different medium. And so you just have to show up.

spk_0 So the final thing we do is working at our cause. Is there a nonprofit that you like to support?

spk_0 And we will contribute to them and then link to them in the show notes. I appreciate this.

spk_0 There is a group of kids. They are students at the food and finance business school.

spk_0 It's like the weirdest title ever for what it really is. This food, this high school is the

spk_0 culinary version of the La Guaria School. Think of everything that you know about a fame school.

spk_0 But instead, in addition to their, their basic classes, they learn how to bake, how to make sushi,

spk_0 how to do irrigation systems, how to work with plant food and indoor farming.

spk_0 Wow. How to, and it's a passion of theirs. When it first opened, it was more like, well,

spk_0 these students are the lowest testing score of all men hat. And so let's at least do home

spk_0 economics to school. Maybe they could be a, a maiden hotel or work at a McDonald's.

spk_0 Right. But the opposite happened. And now a lot of our students are discovering their,

spk_0 their culinary passion. And yeah, they, they attend the food and finance business school,

spk_0 which is essentially the food version of the fame school. Wow. Yeah. That is so cool. So we're

spk_0 going to contribute to them. We'll link to the show notes encourage people to contribute as well.

spk_0 Thank you. Appreciate it. Mayor, it's been an honor. Thank you for having me here. You're,

spk_0 you're wild inspirational. I'm going to go work on writing my third movie right now because I,

spk_0 everything you say fills me up with inspiration. So I feel lucky to know you.

spk_0 My fan of the show and I'm glad to be one. Thank you, sir. Thank you.

spk_0 That's going to do it for another episode of working it out. You can follow Quest Love on Instagram,

spk_0 at Quest Love. You can check out his documentaries on SNL music on peacock or sliced stone on Hulu

spk_0 or Disney Plus. I highly recommend them. You can watch the full video of this episode on our YouTube

spk_0 channel. My YouTube channel is Mike Burbiglia. Check that out and subscribe. We are posting more and

spk_0 more videos. Check out Burbigs.com to sign up for the mailing list and to be the first to know about

spk_0 my upcoming shows. Our producers are working out our myself along with Peter Salomon, Joseph

spk_0 Burbiglia and Mabel Lewis, associate producer Gary Simons, sound mix by Kate Belinsky,

spk_0 special thanks to Jack Hansenoff and bleachers for their music. Special thanks as always to my wife,

spk_0 the poet J. Hope Stein and our daughter Una who built the original radio for it made of pillows.

spk_0 Thanks most of all to you who are listening. If you enjoy the show, please rate us and review us.

spk_0 On Apple Podcasts, it really helps out. And if you're new to the podcast and enjoyed this one,

spk_0 we have over 160 more episodes that are evergreen and not behind a paywall. For the last almost

spk_0 five years, they're all free. We've had Rachel Feinstein and Jimmy Fallon and Roy Wood Jr.

spk_0 and so many great folks. Check out our back catalog comment on Apple Podcasts, which is your favorite

spk_0 that helps people find it. Thanks most of all to you who are listening. Tell your friends, tell your

spk_0 enemies. Let's say one of your enemies is self-sabotaging. They could be achieving more and they could be

spk_0 nicer to people and you just know it deep in your soul and you think, I want more for my enemy.

spk_0 You could say to your enemy, you go, hey, I know this podcast where Mike Burbiglia and Questlove

spk_0 talk about this exact thing and you could watch a documentary after that. That's exactly about that

spk_0 theme and maybe that enemy will come around and maybe not be your enemy anymore. Thanks everybody.

spk_0 We're working it out. We'll see you next time.

Questlove: The Art of Self-Sabotage

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