Questlove spins the soundtrack of his life in 'Music is History'

TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross.

When I interviewed Ahmir "Questlove" Thompson over the summer after the release of his documentary "Summer Of Soul," at the end of the interview, I immediately invited him to come back when his book was published in the fall. Well, it comes out next week, and I'm happy to say Questlove is back to talk with us about the book.

He's the co-founder of and the drummer in the hip-hop band The Roots, which is, among other things, the house band for "The Tonight Show With Jimmy Fallon" (ph). He's also the show's music director. He's won five Grammys. Among the things he's famous for is knowing thousands and thousands of records and being a much sought-after DJ. At President Obama's request, Questlove DJed Obama's final White House party in January 2017.

The story behind that is one of the many stories Questlove tells in his new book, "Music Is History." It's a year-by-year series of songs that have meant a lot to him from 1971, the year he was born, to the present. He describes what makes each of those records important, the place they hold in his life and how they reflect what was happening in America at the time. The book also includes a collection of playlists he's put together, ranging from songs he learned through other groups' samples to short songs that help him think about how stories can be told with brevity. We'll be hearing some of the records he writes about.

Questlove, welcome back to FRESH AIR. I'm so glad you've come back.

QUESTLOVE: Thank you for having me. I appreciate it. Thank you.

GROSS: So let's start with a record from the year you were born. And this is a record that seems to have a lot of significance to you. It's a Tony Williams Lifetime album called "There Comes A Time." And Tony Williams used to be the drummer with Miles Davis, and he started drumming with him when he was - when Tony Williams was, like, super young, still in his teens.

QUESTLOVE: Yeah, he was like 15, 16. Yeah.

GROSS: Yeah. And the track you've chosen from the year that you were born, 1971, which you didn't hear until years later - this is actually a vocal track with Tony Williams singing. So what is it about the lyric that really reached you?

QUESTLOVE: More or less his singing delivery. Because of having perfect pitch, I'm really sensitive to when people are off-key or just a little pitchy - as singers say, pitchy - or even with rhythm, when they're off rhythm. And - which is weird because now I embrace mistakes. But back then, I was like the hall monitor. Ah, that's off.

GROSS: (Laughter).

QUESTLOVE: So, yeah, when Tony Williams starts singing, to me, it felt like the twins in Stanley Kubrick's "The Shining" - like, the way that they're standing in the hallway. He just sounds real eerie. (Singing) There comes a time when you want to - like, it doesn't - the melody doesn't match the music at all, and it hit me. And, you know, on top of that, the DJ that was playing it on that jazz station wound up being my manager until his dying day - Richard Nichols, who at the time was a Temple University jazz station DJ. So, yeah, it just - it sounded very eerie because it was off-key slightly.

GROSS: And what about the lyric, there comes a time when you want to be older; there comes a time when you want to be bolder? Did you relate to that?

QUESTLOVE: You know, I've been trying to interpret that for the longest, and it didn't make sense until I made the decision at my manager's funeral, at his homegoing service that we were going to do that song because that's the way that he entered our lives. And I realized that all those lyrics really described Rich. And it really hit me, especially the line, I love you more now that it's over. And I thought that was a really apropos way to send him to the next life.

GROSS: Well, let's hear it. This is Tony Williams from 1971, the year Questlove was born. This is "There Comes A Time."

(SOUNDBITE OF SONG, "THERE COMES A TIME")

THE TONY WILLIAMS LIFETIME: (Singing) There comes a time when you want to be older. There comes a time when you want to be bolder. I love you more when it's over. I love you more when it's over. There comes a time when you're helpful. There comes a time...

GROSS: So that's Tony Williams' "There Comes A Time," recorded in 1971, the year Questlove was born. And that's one of the songs he writes about in his new book, "Music Is History."

You have a chapter on blaxploitation films and their soundtracks in your 1972 year, and you talk about "Shaft" and "Super Fly," "Across 110th Street." So you were too young - you were like 1 year old when those movies came out. But what do they - what do the soundtracks from those films come to mean to you?

QUESTLOVE: In the case of "Super Fly," the reason why it's so connected to me was basically because oftentimes, music can also mark tragedy. And I know it's kind of weird. Like, half of these - almost more than half of the songs that I've chosen for the book are sort of marred by some sort of tragic event that goes with it. But in the case of Curtis Mayfield's classic "Super Fly" soundtrack, I had an accident once when I was 2 years old. I just got out of the bathtub, and I was running around the house. And we happened to have - we had a very unusual radiator that's made of, like, metal. And it was almost like touching an iron when you iron your clothes. And all I remember was that Curtis Mayfield was singing "Freddie's Dead" on "Soul Train," and mid-song, the second that my entire right leg landed on this radiator and practically burned my skin off, the song went to a modulated key. And almost to this day, I get a chill. I mean, I have a better relationship with it now. But back when I was younger, if ever a song modulated and went to a whole 'nother key, like, dramatically, that was like the equivalent of, like, the Boogie Monster under the bed or - like, it just scared me. Like, I'd turn all the lights on. And so, yeah, I have a very weird relationship with music as well. So it took a long time for me to really get over keys modulating.

GROSS: So key modulations gave you PTSD.

QUESTLOVE: It did. It did for the longest. Like, it was - I was maybe 16 before those burn marks, like, weren't on my leg anymore, so...

GROSS: Whoa. Do you think part of the reason you play drums is that you don't have to play key modulations? There's no...

QUESTLOVE: You know...

GROSS: There are no chords when you're playing drums.

QUESTLOVE: (Laughter).

GROSS: I mean, there's tonal shifts, but they're not chords.

QUESTLOVE: Yeah, they're not chords. I really don't know. That's something to think about. It's a - that's a good observation.

GROSS: So which part of "Freddie's Dead" should we play?

QUESTLOVE: You can go do the scary part. I'm fine.

GROSS: (Laughter).

QUESTLOVE: In the middle when the song changes to the next key - that's the part.

GROSS: OK. So let's hear it.

(SOUNDBITE OF SONG, "FREDDIE'S DEAD")

CURTIS MAYFIELD: (Singing) Hey, hey. Love, love. Hey, hey. Yeah, yeah. Ha, ha. Love, love. Yeah, yeah. Ha, ha. Yeah, yeah. Freddie's dead.

GROSS: OK. That was the part that modulates in "Freddie's Dead," which...

(LAUGHTER)

GROSS: Can you still listen to that without getting thrown back into a state of fear?

AHMIR THOMPSON: I cannot separate my brain from thinking about that moment. The second that happens, it's just - put your thigh on an iron for about five seconds. Like, that's what it feels like. So...

GROSS: Wow. OK.

THOMPSON: Yeah.

GROSS: I think we need to take a short break here, so let's do that and then we'll talk more. If you're just joining us, my guest is Ahmir "Questlove" Thompson. He has a new book called "Music Is History." We'll be right back after this break. This is FRESH AIR.

(SOUNDBITE OF MUSIC)

GROSS: This is FRESH AIR. Let's get back to my interview with Ahmir "Questlove" Thompson, co-founder of the hip-hop band The Roots, which is the house band for "The Tonight Show With Jimmy Fallon." Questlove directed the documentary "Summer Of Soul," which was released over the summer. His new book is called "Music Is History." He chooses one or more recordings from each year since his birth in 1971 and describes their personal and historical significance.

Let's move forward a few years now. We could stop in 1978, in which you write about disco. You were 7 at the time. You have interesting thoughts about disco, about how some of it was actually interesting. A lot of it was just very kind of almost like a factory churning it out. But one of the things you say that I found really interesting is that you thought disco was kind of tragic for some of the musicians during that period. Can you talk about that a little bit?

THOMPSON: Yeah. I can only imagine that - to have to be as disciplined as a musician - to be that disciplined could be somewhat constraining. But I understand that the purpose of it was to play something for 12 minutes so that the party can last longer. And the more that you just stay repetitious, the more effective it is. But I don't know if that's satisfying to the soul as a musician. So that's why I said that.

GROSS: Something I had to go back and listen to because I hadn't heard it before is that James Brown had a disco recording called "The Original Disco Man." I don't know what you think of it. I think it's so bad. You know, it was a period when everybody was kind of forced to do a disco recording because that's what was selling. And all kinds of people were put in the disco format with horrible results. And I think, wow, this is a really strange example of it.

THOMPSON: OK. So for a James Brown-ologist, there's really two ways to look at his album canon. And really, when you're talking about his true zone, you're kind of talking 1967. Even though he had hits before '67, '67 is where I feel the true paradigm shift of him inventing funk music comes into play. And, you know, every album was absolutely a miracle because he was writing - he was Moses. He was, you know, he's getting the tablets from the hand of God to feed the earth. And then 1975 came, and you clearly realized, like, OK, well, that streak's over. Like, we had James Brown, you know his commandments from '67 to '74.

However, James Brown is such an interesting figure because he doesn't make mediocre music. It's either the most life-changing classic music ever or equally horrible music. And the fact that...

GROSS: (Laughter).

THOMPSON: I don't know. I respect, even if it's horrible, it's interesting. In my opinion, he's never made a bad record. It's just what we would deem classic and horrible. He was never mediocre, which is great, fine by me. I would love - I have a dream to make a horrible record, like really commit to making a bad record.

GROSS: (Laughter).

THOMPSON: Because I think at the end of the day, you just have to be interesting.

GROSS: So should we hear just a little bit of a James Brown horrible record?

THOMPSON: Depending on which song you want to play.

GROSS: He's "The Original Disco Man."

THOMPSON: The title cut? Yes, that's absolutely, positively a great example of that. Yes.

GROSS: OK, so we're playing this as a curiosity with no disrespect to James Brown. So...

THOMPSON: Oh, absolutely not. I think it's classic...

GROSS: OK.

THOMPSON: ...In the weirdest way possible.

GROSS: OK. And this is from the 1978 chapter of Questlove's new book, "Music Is History." That's where this song fits in.

(SOUNDBITE OF SONG, "THE ORIGINAL DISCO MAN")

JAMES BROWN: (Singing) In 1955, people were dancing to all kind of jive, yeah. In 1966, you all got down with my funky licks. Uh-huh, yeah. Hit it.

UNIDENTIFIED SINGERS: (Singing) He's the original disco man with the original disco band. He's the original disco man. His groove is where it all began. He's the original disco...

GROSS: That was James Brown during the disco era, where everybody was forced to make disco recordings (laughter). And yes, it's one of the songs referred to in Questlove's new book, "Music Is History." OK, let's go to another song. And this is a song by The Police, who I was a little surprised to see in the book. But this is a song with real personal significance to you, in part because of the lyric and also because of the production.

QUESTLOVE: Yeah.

GROSS: So tell us what about the lyric reached you? Now, I should mention, the song itself came out in '79. But you didn't hear it until two years later, in 1981, when you were 10. What was it about the lyric that you responded to?

QUESTLOVE: I think it was, like, one of the first self-deprecation songs that I heard. You know, I changed my clothes 10 times before I took you on a date. And, you know, I'm so nervous and scared and that sort of thing - and, you know, especially, like, at age 10, when I was, like, really starting to like girls and all those things and was real shy to approach them, had low self-esteem and that sort of thing. It's like, oh, yeah, I relate to this guy, the loser guy. And I don't know why, but that song, like, just always stuck with me until very recently, when I realized, like, you know, I have to get out of that mentality of, hi, guys. How are you doing? Like - so really, honestly, wasn't until last year that I realized that that's almost, like, a dangerous practice that we all somehow participate and get into, like, this addiction to sadness.

GROSS: In the book, you say you had a lot of social anxiety when you were young and that this lyric really spoke to you about that.

QUESTLOVE: I still have social anxiety (laughter).

GROSS: Was it helpful to find the word social anxiety, to have, like, a word describing the feeling?

QUESTLOVE: I'm a self-admitted reluctant leader. I have miraculously found awesome ways to become this sort of iconic figure without ever having to leave my post. Like, I'm kind of like "Wizard Of Oz."

GROSS: Yeah. Yeah.

QUESTLOVE: I hide behind Tariq. I hide behind Jimmy Fallon. I hide behind these books. I hide behind my Instagram posts. Like, everything that I've done always has a shield that prevents people from really, really, really getting to me. Even as I reveal things, like, it's always, like, from a distance.

GROSS: You know, on that note, I think about you DJing at parties. So - like, on the one hand, like, you're the center of the party. On the other hand, you're not in the middle of the party. You're set apart from it, at the turn tables.

QUESTLOVE: Oh, absolutely.

GROSS: You don't have to talk to people. You don't even have to dance. (Laughter) You could just be spinning the records or tapes or whatever it is that you're doing there. So is that part of the pleasure of DJing is that you could be in the party, be the center, but not have to be socially present?

QUESTLOVE: Absolutely. It makes me omnipresent. It gets me all the elation in the world if I play the right song. And it allows me to be antisocial.

GROSS: (Laughter) Yeah.

QUESTLOVE: Like, the yelling - whoop - that's enough for me. Like, when I hear...

GROSS: (Laughter).

QUESTLOVE: If you play the right song, whoop.

GROSS: So we should hear The Police doing "Does Everyone Stare," Which is the song that has led to this part of the conversation. And it's one of the songs that Questlove writes about in his new book, "Music Is History." The song is from 1979, but Questlove first heard it in '81.

(SOUNDBITE OF SONG, "DOES EVERYONE STARE")

THE POLICE: (Singing) I change my clothes 10 times before I take you on a date. I'm in a cold sweat, I panic, and it makes me late. I knew you never asked for this. I know my shots will always misfire. My shots will always miss. Does everyone stare this way at you? I only look this way at you. I change my clothes 10 times before I take you on a date. I get the heebie-jeebies, and my panic makes me late. I break into a cold sweat, reaching for the phone. I let it ring twice before I chicken out and decide you're not at home. Does everyone stare the way I do? I only stare this way at you. I never noticed the size of my feet until I kicked you in the shins...

GROSS: So that was The Police recorded in 1979. And it's one of the songs that Questlove writes about in his new book, "Music Is History." We're going to have to take a short break here, so let's do that and then we'll be right back. We'll talk more, and we'll hear some music. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF SONG, "UPPER EGYPT")

QUESTLOVE: You can't hear the guitar, Kurt. But it's just basically like a, (vocalizing) - like a "Chicken Grease" chord. Yeah.

(SOUNDBITE OF MUSIC)

UNIDENTIFIED MUSICAL ARTIST: All right, Afrobeat (ph). Go back (ph). Angry solo (ph).

GROSS: This is FRESH AIR. I'm Terry Gross. Let's get back to my interview with Ahmir "Questlove" Thompson, co-founder of the hip-hop band The Roots, the house band for "The Tonight Show With Jimmy Fallon." He's also the music director on the show. He directed the documentary "Summer Of Soul" about the 1969 Harlem Cultural Festival. That film was released over the summer. In his new book, "Music Is History," he chooses one or more recordings from each year since his birth in 1971 and describes their personal and historical significance.

Your new book is a year-by-year history of songs that have special significance for you since your year of birth in 1971. For 1988, you write about Public Enemy's album "It Takes A Nation Of Millions To Hold Us Back," which is a...

QUESTLOVE: Yeah.

GROSS: ...Pivotal record for a lot of people. I think it was maybe especially pivotal for you, both in terms of, like, music, but also changing the course of your life.

QUESTLOVE: Yeah.

GROSS: You were working at a '50s-themed fast food place in Philly?

QUESTLOVE: Big Al's.

GROSS: Where was that?

QUESTLOVE: It was on Penn's campus, on 34th and Walnut. All I can simply say is that I think every teenager has that one moment in his life or her life or their life in which the possibilities of what life has to offer is shown to you, and it's up to you to accept that mission or to ignore that mission.

GROSS: Well, how did that music - how did that album tell you that you needed to change the direction of your life and quit your job at Big Al's?

QUESTLOVE: OK. So what makes Public Enemy one of the most important artists ever is the fact that in one fell swoop, they literally made my dad's entire record collection cool because their pop art, Jackson Pollock method of just throwing paint on the wall and watching these colors blend in with each other, that's how they treated records. So I'm listening to their music, and it's like, wait a minute; that's David Bowie. Wait a minute; that's George Clinton. That's James Brown. That's the Commodores. That's the Bar-Kays. Like, I'm - you know, I'd listen to it one down to see, like, how many sound bites could I recognize from my dad's record collection? And once I went over a hundred, I was like, wait a minute; this is my dad's record collection in one record. It's like a catalog. I can do this.

But it was done in a way in which - it just didn't sound like - it wasn't like they were mirroring that my dad's record collection. It was like they filtered it and made it sound urgent. And it was like hearing - I could imagine it was like what it was like to hear the Sex Pistols or Bad Brains or punk music for the first time. Like, I had that for me. And when I got to work, I couldn't stop thinking about that record. And when I went on my lunch break, I never went back. I just sat in the park and listened to that record for four hours. And I said to myself, this is what I want to do with my life. Like, I want to make a kid quit his job and change his life direction. This is what I want to do. Like, not just, like, make music or get a record deal - like, the way that music made me do those things, this is when I said, this is my direction.

GROSS: Well, you were already playing with The Roots, right?

QUESTLOVE: We were a year into it. But, you know - I mean, to be honest with you, I - you know, The Roots kind of started with a lie. Like, I was just trying to impress a girl that I liked in high school. And I was just thinking off the top of my head - yeah, I got a group with that guy. And, you know, I ran up to Tariq like, yo, we got a group in case blah-blah-blah ask you, all right? And Tariq was, like, baffled. Like, huh?

GROSS: (Laughter).

QUESTLOVE: Yeah, yeah. We got a group. And then that's kind of how it was. Like, we'd just freestyle at lunch period. Like, we did one talent show, and Boyz II Men got all the attention and all the girls crying in the audience and all those things. And you know - so I didn't truly expect - like, I was going to follow my father's dream. My father wanted me to go to Curtis Music Institute. In his mind, like, going a classical - the classical route and making, you know - you could make $100,000 a year playing classical music. You know, that was like respectable, which is why people always ask me, is it true you really didn't tell your dad about The Roots until the second album? And it's like, yeah, because, you know, this is you defying your parents - defying your father. My mother hates when I tell that story 'cause she doesn't want the world to think that she didn't encourage me. She did encourage me. But you know, to tell your dad, you're not going to go to Juilliard and you're going to get a record deal with your high school friend, like, that's - that isn't the reason why he, like, you know, busted his behind to put you in the best schools to, you know, "to quit to do rap music," end quote.

So - but yeah, I heard that record, and it just absolutely - that was my Moses-come-to-the-mountain moment in my life.

GROSS: So which track from "It Takes A Nation Of Millions" best illustrates your father's record collection?

QUESTLOVE: His absolute disdain for the track "Rebel Without A Pause" - he thought it was a teakettle going off and just thought it was absolute noise. And you know, little did he know, that was just his beloved James Brown loop being repetitive. And, you know, he couldn't argue with me there.

GROSS: (Laughter) OK, so let's hear it.

(SOUNDBITE OF SONG, "REBEL WITHOUT A PAUSE")

PUBLIC ENEMY: (Rapping) Yes, the rhythm, the rebel. Without a pause, I'm lowering my level. The hard rhymer, where you never been, I'm in. You want stylin'? You know it's time again. D, the enemy, tellin' you to hear. They praised the music. This time, they play the lyrics. Some say no to the album, "The Show," "Bum Rush," the sound I made a year ago. I guess you know. You guess I'm just a radical. Not on sabbatical, yes, to make it critical. The only part your body should be partyin' to - Panther power on the hour from the rebel to you.

Ay, yo, Chuck, man, I don't understand this, man. Yo, we got to slow down, man. You losin' 'em.

(Rapping) Radio suckers never play me. On the mix...

GROSS: That's Public Enemy from 1988. And that's a song from one of the albums that Questlove writes about in his new book, "Music Is History." Well, let's take another short break here. We'll be right back. This is FRESH AIR.

(SOUNDBITE OF THE ROOTS SONG, "PROCEED IV [A.J. SHINE MIX]")

GROSS: This is FRESH AIR. Let's get back to my interview with Ahmir "Questlove" Thompson. His new book is called "Music Is History." And in the book, he chooses one or more recordings from each year since his birth in 1971 and describes their personal and historical significance. He's a - he's the co-founder of the hip-hop band The Roots, the house band for "The Tonight Show With Jimmy Fallon." And he directed the documentary "Summer Of Love," which came out over the summer. And that's a documentary about the 1969 Harlem Cultural Festival.

There's a lot of drama attached to the day you were signed to Geffen.

QUESTLOVE: Yep.

GROSS: It's the day your mother told you she was going to divorce your father. So you're like...

QUESTLOVE: Yeah.

GROSS: You're coming home with this, like, great news, and she's hitting you with this, like - I don't know how you thought of the news of the divorce, but - how did you think about it - like, what was that day, this big collision of, you know, shocking news and great news about your record?

QUESTLOVE: Yeah, it just - first of all, to break the news to my dad that the group even existed in the first place and, surprise, I'm not going to college; here's my record deal; don't get mad - like, that was, like, worry No. 1. But then on top of that...

GROSS: So when you signed the - I mean, when you signed on to the label, your father still didn't know.

QUESTLOVE: He didn't know until it was absolutely unavoidable.

GROSS: Right.

QUESTLOVE: Like, it's hard to keep a secret from your dad when you're on MTV and BET and Rolling Stone.

GROSS: Right.

QUESTLOVE: You're getting all this press.

GROSS: Yeah.

QUESTLOVE: You're, like, trying to hide newspapers and - nothing. But, yeah, literally, the night of our celebration of signing, I was like, all right, I'm going to tell my dad about the band. I mean, I knew that he knew that, like, I was hanging with Tariq a lot, and we were, like, setting up, doing these little demos in my bedroom. But he didn't know that I'm about to sell the family farm on a dream of making it with my best friend and - you know, 'cause he still was like, OK, you're going to college, and you're going to go to - that sort of thing.

GROSS: So let's talk about the news from your mother...

QUESTLOVE: Yeah. So she leaves...

GROSS: ...Hitting you at the same time as you just are celebrating.

QUESTLOVE: Yeah, she laid the news on me at the same time, the night of our - kind of our victory party, which, you know, was really doom and gloom for me because my whole identity was, like, the one kid that had both of his parents in the household, like, the one kid whose - both parents show up at parent-teacher night. Like, I was a special kid. But, you know, I'm also, at this point, 22, 23 and no longer a kid. So in many ways, I just had to - I had to grow up quick.

So this was a trial by fire, you know, standing up to find my dad, becoming my own person, an adult, and also accepting that my mother wanted to - you know, wanted to leave this union that she stayed in just to - you know, just to keep up appearances because we were a showbiz family. So a lot of those things in my past were just - you know, it was literally like burning down the house. Like, we had spent our entire - my entire childhood as a musical traveling family. And the face of the family was very happy. And, you know, we were exemplary of, like, what's awesome about the doo-wop industry - like, Lee Andrews and his kids and his wife do a show together. And all that just came to a halt when I got my record deal in '94.

GROSS: Yeah, your father was, you know, in the group Lee Andrews & the Hearts, which had several hits.

Well, let's take another short break here. If you're just joining us, my guest is Ahmir "Questlove" Thompson. His new book is called "Music Is History." We'll be right back. This is FRESH AIR.

(SOUNDBITE OF SAINT SINNA FEAT. CREEBO LODI SONG, "REAL FLOW")

GROSS: This is FRESH AIR. Let's get back to my interview with Ahmir "Questlove" Thompson, co-founder of the hip-hop band The Roots, which is the house band for "The Tonight Show With Jimmy Fallon." He directed the documentary "Summer Of Soul," which came out over the summer, documenting the 1969 Harlem Cultural Festival. His new book is called "Music Is History." He chooses one or more recordings from each year since his birth in 1971 and describes their personal and historical significance.

So I'm going to skip ahead to 9/11 and - 'cause you write about what that was like for you in your new book, "Music Is History." So you were in - on 9/11, you were in a hotel in Midtown Manhattan.

QUESTLOVE: Yeah. What makes that day significant was, one, it was Michael Jackson's 30th anniversary, so hotels were booked. And it was also fashion week 'cause it's September, and that was booked. And Bono had just started his Red organization for AIDS research. And all the hotels were booked. So initially, the hotel we had had lost our reservation, and there was a brief moment for four hours in which I personally was booked inside of the Marriott Hotel inside the World - right next to the World Trade Center.

GROSS: No, really?

THOMPSON: The only thing that saved me was the fact that usually around 1:00 in the morning or 2:00 in the morning, hotels will refresh their system. And, you know, depending on the computer they have, it takes two or three hours. I wasn't willing to wait till 5:00 in the morning. So luckily, one of the people that brought us there was like, look, I got a place at Bryant Park. You could take one of those rooms. And it was like, no, I'll wait. Room's almost done. And - no. I don't know why, but I went to the Bryant Park, where normally I would have just insisted I'll sit in the lobby until my room's ready. And yeah, I narrowly - I left that hotel around 4:00 or 5:00 in the morning, not knowing that in two hours what was going to happen. So yeah, I wound up in the Bryant Park Hotel.

GROSS: That's an amazing story.

THOMPSON: Yeah. And...

GROSS: So you find out what happens. You know, people are calling you and texting you. You find out what happens. And your first response is, OK, you extended your stay at the hotel. And then you paid a taxi driver $100 to take you to the Virgin record store, which is a few blocks away. It's just amazing that your first reaction was I got to get some more music. It's like, the world may be ending, I'd better get some more records. Like, what was going through your mind when that's what you did?

THOMPSON: I'll be honest with you. The way that Prince describes what the apocalypse was like in "1999," the song, that's kind of what was happening. Like, when I tell you - I was just - I was disheveled because, one, you know, I heard the phone ringing in my sleep. And I didn't know. And when I looked at the phone, I saw that there was 18 missed calls from my mother. And instantly I thought, oh, my dad just died. And I can't take this right now. I need two hours just to process the bad news. Like, I didn't even call her back.

So it wasn't until 11:00, maybe 10:00 or 11:00 that I finally called my mom to brace myself for the news that she's about to give me. And then she tells me something else. And I'm like, huh? And I turn the TV on and see what's happening. And then I was like, wait. I didn't know none of this was happening. I thought you're about to give me bad news about dad. Like, why else would you call 20 times in a row? And I ran downstairs.

And my - just the world was - my band was running like, text him, text him. And I'm like, what's going on? What's going on? And they're like, we're in front of the Philadelphia. The world's ending. Like, that's how they told me. And, you know, I didn't have my luggage. And I was like, wait. Can I stay here? Said, you can stay here if you want to, but I ain't staying in New York City. And I just took five minutes out. And I that was just like, all right, if this is the end, what do you want to do? And I hate to say this, but - and this is kind of the basis of our friendship now, me and Jay-Z. I was just like, I got to hear what this Jay-Z record sounds like. I can't - I'm sorry.

(LAUGHTER)

THOMPSON: So I ran - I had my wallet on me. And I saw a taxi. And, you know, he seemed rather calm. He was like the only calming figure out there. I said, can you drive to the Virgin Megastore real quick? And I gave him $100. I said, do me a favor, just keep the meter running. Can you give me 20 minutes? I'm just going to run and get some things. He's like, yeah. I said, you'll stay here for 20 minutes? He said, absolutely. And I ran in. And just imagine, like, "Flight Of The Bumblebee." (Vocalizing). I ran, I rummaged through the entire DVD section. I rummaged through all - I brought records I had already. I just thought, well, this might be the last record store experience I have. So I purchased like $5,000 worth of music.

GROSS: Wow.

THOMPSON: Came out with like eight bags. And I just went in my room, which is weird enough because I only listened to "The Blueprint." I got to my room.

GROSS: That was the Jay-Z album.

THOMPSON: Yeah, yeah, the Jay-Z record. That's all I did. I just sat there and listened to it. And a funny thing happened. I liked that record.

GROSS: Were you not expecting to?

THOMPSON: In which I was, quote, "supposed to not" - "I was supposed to not like that record." Like, there was there was an apartheid happening in hip-hop between the haves and the have-nots. The successful rappers were looked at as like the compromisers, the devils, the evil-doers. And we were like the liberals, like, we were the - you know, we were the creatives. And we put creativity before money. And I told a mutual friend of mine - of Jay's, I was like, yo, I would never say this in public, but I kind of like this Jay-Z record. And this person took it as a cue, was, like, yo, I have to tell Jay-Z this. I was like, no, no, no, don't tell him because he's the devil and...

GROSS: (Laughter).

THOMPSON: He's just like, look. I want you to breathe. This is important. I'm telling Jay that you like the record. And I really thought, like, my career was going to end. Like, what if the world finds out I talked to a rich rapper? And she came back to me and said, you know what? That really touched him because it's one thing for, like, his fan base to like it. But the fact that he made you - and the thing was, like, Common also told her, like, yeah, I like this record, too. Like, we were scared to let the world know that we liked this Jay-Z record, that he wanted to talk to me the next day. And I was like, no, I'm never calling him back.

So I, like, avoided him like the plague for, like, three weeks. He wanted to ask me if we would be his band for "MTV Unplugged." And I just thought that was the most riskiest thing ever. Like, what will - my families will think I'm selling out if I'm playing with a rich rapper. And it turns out, like, Jay is one of the most - he's one of my favorite people to work with of all the people I ever worked with. Like, it turned out to be one of the best experiences ever. And you know, it it changed our lives really.

GROSS: Well, we should hear something from "Blueprint," from the Jay-Z album that you're talking about. What would you like to play from it?

QUESTLOVE: Um, wow. It's - let's see. Probably I would play "Izzo," the most popular cut on that record produced by Kanye West - "Izzo."

GROSS: OK. Let's hear it.

(SOUNDBITE OF SONG, "IZZO (H.O.V.A.)")

JAY-Z: I appreciate that. (Rapping) H to the izz-O, V to the izz-A. For shizzle, my nizzle, used to dribble down in VA, was herbing 'em in the home of the Terrapins, got it dirt cheap for them. Plus if they was short with cheese, I would work with them. Brought in weed, got rid of that dirt for them. Wasn't born hustlers, I was birthing 'em. H to the izz-O, V to the izz-A, for sheezy, my neezy, keep my arms so breezy. Can't leave rap alone. The game needs me. Haters want me clapped in chrome. It ain't easy. Cops want to knock me. DA want to box me in. But somehow, I beat them charges like Rocky. H to the izz-O, V to the izz-A Not guilty, he who does not feel me is not real to me, therefore he doesn't exist. So poof, vamoose, son of...

(Rapping) H to the izz-O, V to the izz-A. For shizzle, my nizzle, used to dribble down in VA. H to the izz-O, V to the izz-A. That's the anthem get your damn hands up. H to the izz-O...

GROSS: That was Jay-Z from his album "Blueprint," one of the albums that Questlove writes about in his new book "Music Is History," a year-by-year history of songs that have meant a lot to him since the year of his birth in 1971.

So just playlists - the book is filled with playlists. And that's one of the things you're famous for. Obama asked you to do a playlist, and you never finished it. You - like, you were so conscientious about wanting to do, like, the perfect song for each, you know, for each track on the playlist.

QUESTLOVE: It took me for - yeah, by the time his presidency ended, I think I was still on, like, the letter P. And then I just realized the playlist never ends. Like, even to this day - since the beginning of "The Tonight Show," I've spent an hour every day chipping away from music to add to the playlist. And it still never ends.

GROSS: Wait. You're still working on the Obama playlist?

QUESTLOVE: It's weird because I just did his 60th birthday party. He allowed a redo. If you remember the last time I was on your show, I mentioned, like, how disastrous the White House gig was, me overthinking it. And I did a redo. And I promised that, yeah, I was going to get him his weekly allowance. I don't know why I keep procrastinating with him because, you know, with everyone else, I'm pretty much - you know, I feed them playlists. Like, just this week, Diddy called me and says, yo, I heard you're doing playlists for people. I do it for Mariah Carey. I do it - like, I do these weekly playlists for people. And I feed them an hour music at a time like it's a prescription. But I don't know. With him, I'm so nervous to share music with him because, you know - and he told me, like, you overthink everything. Like, just let it go, and just share the music. And I'm like, no, it's not ready yet. So...

(LAUGHTER)

GROSS: Someday.

QUESTLOVE: One day - yeah, one day - I promised him this year for 60th that I'd start his allowance. And it's always when he does his summer list thing that I feel the need to really intervene and give him music that he needs to be listening to.

GROSS: It's been great to talk with you again. Thank you so much for coming on our show. I always really enjoy our conversations.

QUESTLOVE: Thank you. I love talking to you, too. Thank you.

GROSS: Ahmir "Questlove" Thompson's new book is called "Music Is History."

Tomorrow on FRESH AIR, we'll hear a remarkable story of beating the odds. Our guest will be Richard Antoine White. As a young child, he slept in abandoned houses and parks in Baltimore, but he became the first Black American to earn a doctorate in tuba performance and is now principal tubist for the New Mexico Philharmonic. He has a new memoir called "I'm Possible." I hope you'll join us.

(SOUNDBITE OF MILES DAVIS' "IT COULD HAPPEN TO YOU")

GROSS: FRESH AIR's executive producer is Danny Miller. Our senior producer today is Sam Briger. Our technical director and engineer is Audrey Bentham. Our interviews and reviews are produced and edited by Amy Salit, Phyllis Myers, Roberta Shorrock, Sam Briger, Lauren Krenzel, Heidi Saman, Therese Madden, Ann Marie Baldonado, Seth Kelley, Kayla Lattimore and Joel Wolfram. Our digital media producer is Molly Seavy-Nesper. Thea Chaloner directed today's show. I'm Terry Gross.

(SOUNDBITE OF MILES DAVIS' "IT COULD HAPPEN TO YOU")
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