Jeff Pearlman on Tupac Shakur: The Myths, the Music, and the Man Behind the Legend

26:01Like it was just stupid. He didn't die for anything. I hate that he didn't die for anything. He should have been a guy, honestly, who stood up to police as he had done in the past as they were like brutalizing a black motorist and go out that way or should have gone out leading a march or should have gone out in the Middle East standing up for whatever. You know, like he had greatness about him and he died in such a not great way. How did the guy who actually pulled the trigger, how did he eventually get caught? Because it was only in 2023. He didn't get caught. He got shot. He got killed. All right.

26:33He was murdered. Yeah, he was murdered. How did they know though that it was him? I don't even remember. It was like two years after he shot Tupac. Was it two years after he shot Tupac? It was a decent amount of time after he shot Tupac. And he was killed in a revenge killing and that was it. you know and you know the the irony is like biggie and tupac were i don't know if they were friends at that exact moment but like when tupac was first shot you mentioned in the book how biggie and puffy even showed up at the hospital correct and then biggie wanted to uh visit him when he was in clinton a clinton correctional facility the prison tupac was like f that guy i'm not letting him come biggie was dumbfounded that tupac held him in blame for his shooting at quad studios um so you know it's kind of a weird it's all just it's sad the whole thing is sad it was this time period where people were caught up in something that was half real half contrived that didn't really mean anything these are two gifted young artists smart guys who rose up from tough circumstances to become you know great and for them to both go out like that is just disturbing it just sucks it's no different than kirk cobain's death it's another it's a it's a senseless time period of artists you know Shannon Hoon of Blind Melon and you know these guys and Cobain it just sucks it all sucks I hate it all I do take a quick break if you like this episode I'd really really appreciate it it would mean so much to me please share it with your friends and subscribe to the podcast email me at alcatra at gmail dot com and tell me why you subscribed thanks

28:20This November, action is free on Pluto TV. Go on the run with Jack Reacher. Every suspect was a train killer. Then buckle up for Drive, World War Z. Every human being we save is one less fight. And Charlie's Angels. Damn, I hate to fly. Launch into sci-fi adventure with the fifth element and laugh through the mayhem in Tropic Thunder. What is going on here? All the thrills, all for free. Pluto TV. Stream now. Pay never. Being an entrepreneur is a 24-7 job. And when you're hiring, you need a partner that works as hard as you do. That hiring partner is LinkedIn Jobs. When you clock out, LinkedIn clocks in.

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30:13Capital One, what's in your wallet? Find out more at CapitalOne.com slash Spark Cash Plus Terms Supply. I feel like at that exact time, like the mid-90s, Shakur and Biggie were probably the two best storytellers. I always thought of their rap as like, they were great storytellers. As opposed to, you know, every rapper was good at something, but for them, it was the storytelling. And in In some ways, they were very similar, I felt. Yeah. Well, I mean, I think Tupac had something big he didn't, which is Shaq G from Digital Underground talked about it. A lot of rappers rap from the nose and the mouth, from the throat, and that Tupac rap from the stomach, from the gut.

30:55And I do think he and DMX later shared that thing where it's like, ugh. It's not just I'm telling you a story. I'm making you feel this story. Like I'm putting a bunch of rocks in your hand and you need to feel the weight of it. I do think Tupac had that. yeah man i think both big and the crazy thing is tupac was really a new york trained rapper like he was learning there learning to rap and rhyme and do stuff on the streets of new york on the on the steps outside his aunt's apartment in the bronx like he wasn't really a west coast rapper i mean he identified with the west coast but i would say he was a he was new york born and trained baltimore bred oakland created and los angeles finalized it was funny that he was a Digital Underground.

31:35Like, Digital Underground seemed very different. I mean, I loved Digital Underground when they came out. It was odd that Tupac evolved from that to be Tupac. Yeah. Oh. I mean, same song. Listen to his verse and same song. It's amazing. And I think that Digital Underground changed that guy's life. You know, he was basically, he had kind of given up on hip-hop and was in Atlanta working with a civil rights group as kind of a youth leader. he'd given up he was like to hell with this he was very impatient his whole life very impatient and he gets a call do you want to be a roadie with digital underground and it's like what do you have to what do i do as a roadie it's basically like well you carry stuff you move stuff you lug stuff but we also might give you time on the mic he's like time on the mic i'm in and he moves back to the west coast and immediately starts touring with digital underground and his job there among with you know he would appear on some songs but um but his main thing was he would like be the hype man almost like flavor flay before the act where he'd show up in leopard print underwear uh throwing out like sex packets to the crowd and then he started performing more and more and more so how did he break out from that well first of all they started giving him uh verses and he you know had this idea he wound up getting a a record deal with interscope same label as Digital Underground for this album, To Apocalypse Now.

32:58Used a lot of producers and such from Digital Underground to do it. And he comes out with this song, Brenda's Got a Baby. And Brenda's Got a Baby, for me, kind of put him on the map. So, you know, that was a big thing for him. The arrival of that song and the emphasis of that song. I love the story you tell about Brenda has a baby. Yo. Sure. I mean, I love that song. I think it's insanely important. I do. I think it's really, really important. And he basically was filming the movie Juice in 1991 and he reads an article in the Daily News called Cries in the Night. And the article is about this 12-year-old girl who was raped by a cousin in the Noble Jurali Public Housing Unit in Brooklyn, delivers a baby alone on the bathroom floor, doesn't know what to do, takes a baby, puts it in a plastic bag, throws it down the trash chute.

33:54people are working in the basement that in the lot basement that day where they have the trash compactor it's a day it's supposed to get compacted they hear a baby or a cat crying and the guy who i interviewed finds the baby and is like um is like what the hell is this you know like that what the hell is this and um he uh he basically saves the baby and tubac reads this article, reads the article in the Daily News and says to Omar Epps, his co-star, oh my God, I got to go into my trailer. And he writes a song, Brendan's Got a Baby. So I knew about that story, but no one had ever found the baby.

34:31So I work with a genealogist named Michelle Suli, who's just amazing, just amazing. And she said, let me give it a shot. And a few days later, she comes up with a phone number and she's like, I think this is him. And I reached out to this kid named davon hodge and we ended up meeting at a uh in las vegas where he lives at a starbucks and he's telling me the story trash heap the whole thing he's adopted by las vegas parents they um died a few years ago he does an ancestry.com search all these tentacles come back to brooklyn he reaches out they're like do you know who you are um he's like uh it's like davon they're like well you're you were this, your mom, this article, show him the article.

35:14And we also think you were the inspiration of Brenda's Got a Baby, the Tupac song. He's like, I love Tupac. We think you're that song. All this happens, you know, his visit is amazing. He goes back to Brooklyn. He takes a photo of him next to the trash heap where he was thrown down, meets, you know, aunts and uncles and cousins. But he hadn't seen his mom. So Michelle Suley, the genealogist of the gods, goes back and finds this woman and reaches out to her and says, by any chance, did you have a baby when you were 12 years old? And she's like, who is this? It's, well, my name's Michelle. I work with this author, Jeff Perlman.

35:46We're doing a Tupac book. Is this you? She starts screaming and crying. You know where my baby is? You know where my baby is? Oh my God. What? You know where my baby is? Uh, yeah. And she's like, I need to get home. I'm away from home for a concert. I need to get back to my home in Newark, New Jersey. And she says, well, where do you, uh, what concert are you seeing? Well, I'm seeing the red hot chili peppers I mean, where's the show? It's in Las Vegas. And that night she met with her baby for the first time. And did you ever track down the cousin who had raped the 12-year-old girl who was the father?

36:18I was not able to. In fact, I think that person is dead. Okay. No. And it's interesting because I feel like a lot of art takes the wrong direction when they're trying to have a message, which is that the message is too obvious. and I feel like with that song, he tells a story about this real event that happens and just the telling the story is the impact, not actually kind of deriving meaning from it or applying any sort of meaning to it. Just telling the story is what creates the impact and again, I think a lot of theater is like political theater where they try too hard to say what their message is in the story and with Tupac he's like you say he just got this idea from a New York Post article Daily News and just does it as a song and it becomes like this hit wait it's really interesting you say that actually you're the first person who's brought this up it's funny how we are right like we'll listen to a Bob Dylan song or a Joni Mitchell song or whatever Nirvana doesn't even matter or Livia Rodrigo.

37:29And you're like, wait, what are they talking about? And you'll have someone who will say, well, the tree represents her feelings in the spring and the falling fruit represents her heartbreaking. You know what I mean? And that's really cool. I actually love that. I think that's really neat. I think great songwriting, metaphor and simile and analogies are wonderful. And in a lot of ways, Brenda's Got a Baby is not one of Tupac's best songs because it's extraordinarily literal, right? And it also does sound old-fashioned now. Like it is very, Brenda's got a baby, but Brenda's barely got a brain, a damn shame.

38:03The girl can hardly spell her name. Like it sounds from a different time period in a lot of ways. It's very ba-dum, ba-dum, ba-dum, ba-dum, ba-dum. But I agree with you. I think the literalness of that song is very important. He's just telling a story. It's no different than, I mean, this is going to sound corny, like writer-y, but like you and I sit down for a slice of pizza and you tell me the story about your day. and you're like, I met this amazing guy this morning. He was really interesting. He sold me cell phones, but he also told me he knew God. I asked him why he knew God. And he said, I knew God because he used to go to synagogue as a kid.

38:34Like that's basically what Brenda's Got a Baby is. It's a very literal story, but it's done really well. And the video directed by Alan Hughes, of all people, is fantastic. The black and white, Ethel Love as the mom. It's really good. You know, again, I wonder what, I wonder how Tupac would have evolved in style if he kept going, if he remained alive. Impossible for me to say, but I think he would have, this is also impossible for me to say, but it's a little more of an educated guess. I just think he would have dove much more into acting and maybe faded a tiny bit away from hip-hop. And I think, because it's hard to be an older act in hip-hop.

39:13Most people are not. And they wind up sort of, and this is no indictment of anyone, but like the 90s throwback tour with Kid and Play and Vanilla Ice and Young MC, and it's hard to be Jay-Z, right? It's really hard to be Jay-Z, Nas, Eminem. Like those are the three greats of survival and evolving, but it's an incredible hard medium to do so. So I could see Tupac more taking the, you know, I just think he had that kind of Robert Redford, Pacino, you know, Denzel kind of thing in him. And I also think he would have been a guy who would have like taken to the streets. Maybe he would be congressman.

39:49Can I tell you a two-second crazy story about Tupac that I think explains his direction? Of course. So Tupac had a hip-hop group called Thug Life. And they were touring with a group called Lords of the Underground, a group out of New Jersey, Lords of the Underground. The Lords of the Underground's main rapper was a guy named Dupree Kelly. His nickname was Do It All. Do It All Dupree Kelly. And one day they're in Orlando, and one of the members of Lords of the Underground is late, and they're all in the kind of van waiting to go to the arena and Tupac is getting really mad. And this guy, do it all, Dupree Kelly stands up for his guy.

40:23He's like, no, Tupac, give him time. And Tupac's like, fuck that guy, blah, blah, blah. And again, this heated argument. And Dupree Kelly, they wind up, the gig got canceled, actually. They wind up not going. Dupree Kelly goes back to his motel room. A few minutes later, knock on the door. He looks through the people, and it's Tupac standing there. And before he answers, he picks up the hotel phone, and he calls one of his other guys from Lords of the Underground. He says, yo, Pac is at my door. And guy goes, well, what does he want? He's like, I don't know, but I'm just giving you a heads up.

40:51All right. Answers the door. Tupac is holding some 40s. Someone thought I meant guns. I meant beers, you know, 40, 40 ounces. And he lets, he's like, you ain't gonna let me in? He goes, all right, come on in. He goes, listen, they sit down on the beds. Tupac goes, listen, man, I do not like the way you talk to me. Like, I didn't like that. He goes, but I love, love that you stood up for your guys. I love that you stood up for your guys. That is what we as black men need to do. We don't just need to stand up for our guys. We need to stand up for our communities. And Dupree Kelly's like, what do you mean?

41:27He's like, we need to get involved. We need to represent. You need to represent Newark harder. I need to represent Oakland harder. Cube needs to represent LA harder. In fact, we need to be involved. We can't just have laws made about us. We need to be legislators. And he's like, what do you mean? He's like, we need to start making laws. And that might mean we need to run for office. We need to hold positions. We may need to do that. And when I was interviewing Dupree Kelly, he was a Newark, New Jersey city councilman. And he told me that that talk from Tupac was a talk that set him on his way and truly put it in his head.

42:01And I love that so much. I could not love that story more. And I do believe that was a course that Tupac was headed down. I really do. Well, that's an incredible story. I mean, And look, and you look at the impact rap has had on society, even from back then, like all the debates about censorship, like Two Life Crew, which is the last group you would think to be at the center of a controversy about censorship and then successfully take it all the way to the Supreme Court and win. And yet that happened. That's a thing that happened. Yeah. I played, talking about songs that don't age well, maybe three months ago i played me so horny for my son who's 19 he just had this confused look on his face like how is this a thing because it almost sounds like a parody of rap oh my god i think it secretly i think luke campbell knew it was a parody but like it sets a ridiculous song and it's not even i mean all due respect is that he had a great career and he's had a great prolonged career it's not really that listenable to like i think it was the shock value of that song that really did it.

43:09It was a bizarre time. That was a really bizarre time in hip-hop. Also, a big Miami rap arc when not that much was coming out of Miami as far as hip-hop. Very weird. That was weird. But Luke now is active in the community and he has these baseball leagues. He's amazing. He's amazing. Yeah, he's an amazing guy. A lot of hip-hop artists have really stepped up in the community and they've done stuff and they've got involved. There are no shortage of hip-hop artists who run community centers who started education programs. The thing that people miss, I think, especially white snooty people who don't get it, is these are really intelligent guys.

43:47They're songwriters. They are songwriters, or they're beat makers. Those are not two things that just slow blow can do with an IQ of six. Tupac was wickedly intelligent. Not just intelligent, wickedly intelligent. He wrote songs at a breakneck pace. He had stuff to someone give him a beat top of his head five minutes in. He'd write these songs. I mean, the stories of people told me of him as a songwriter in the studio, hopping back from one console to another, working on this song, working on this song. No, we got to do it this way. Do it this way. He was a brilliant, brilliant mind. He was a brilliant mind.

44:20Like, brilliant, brilliant mind. Like, if he took an IQ test, he would soar past mine, which isn't saying that much. But he was just really intelligent. I think a lot of people look at, oh, those rappers. Right? It's kind of a thing. Oh, those rappers. These are, I don't think I interviewed a hip-hop artist for this book. who is not a very intelligent man or woman. Well, it's got to be hard on so many different levels. Just the production, the musicality, the performance, the storytelling. Who's your, I mean, I have to ask, who's your top five? I would go, this is no word, I'll just do my top five.

44:56Tupac, Nas, Tribe Called Quest, J. Cole, Modern. And I would go Public Enemy, even though it's kind of old school, but I still think Public Enemy resonates. and Black Steel and the Hour of Chaos was the first hip-hop song that really, really, really woke me up to the genre. So there you go. Who are yours? I'm going to be similar, but I throw in Wu-Tang Clan instead of Public Enemy. That's good. I think Nas is a genius. I think Nas, I don't know why, but Nas, he has to be considered one of the five greatest artists of all time, right? For some reason, people overlook him and he's so ridiculous he good and he's the one guy we saw him in concert a couple years ago and he did not feel dated at all at all he's a one guy him i guess jay-z to a certain degree eminem to a certain degree who has defied the hands of time and never became a novelty act in hip-hop i agree about naz and i just saw a video where he's playing with like the boston symphony orchestra or some symphony and it was like an incredible performance i just i loved it also like think how hard that is there's a um there's an album where hanson the rock band hanson plays with the like sydney orchestra and it just sounds not good like it sounds stupid it's a it's almost like they're exposed right like hanson was fine they had a few songs you know whatever but they they sound exposed naz doesn't sound exposed naz is i'm telling you i i don't understand maybe if naz had died at 25 years old we'd be talking about the mystique of naz and there is something i don't say that flippantly.

46:32I mean, there is something about young death that adds to a mystique and makes you talk about someone longer than you would. I always say, if Chuck D had died at 25 years old, we'd be sitting at the altar of Chuck D and saying, oh my God, this guy was this revolutionary who was shot down in his prime. Instead, happily, we've seen Chuck D become a 60-something-year-old man and an elder statesman of hip-hop, which is cool, but it doesn't have the mystique. I think the same goes for a lot of these guys. I think a lot of Tupac and Biggie, they were great, but a lot of it is a mystique of young death also.

47:03Same with Cobain. What if we saw Kurt Cobain get clean and become a folk singer? We'd be like, remember those Nirvana albums? Those are really good. It's kind of weird how it works. I want to throw Mobb Deep onto the list also. I love Mobb Deep. And they had a new album. They just released music and it's good. So there you go. I used to do the websites for all these guys. So in the 90s, I had a company making websites for basically entertainment company. So I did loud records. I did all the bad boy stuff. I did a lot of Interscope stuff. This was slightly after Death Row was a thing. So I had, you know, so Suge Knight was in jail at the time, although I was doing a lot of Interscope artists who had been with Death Row.

47:43And so I was immersed in that whole world then. And, you know, not as much later, but I just, I just loved it all. And then, and then I feel like since the nineties, it just maybe this is me being an old man speaking. I feel like it hasn't been as good, but of course that was my formative year. Here's a trivia question for you. Can you tell me who the first Interscope artists were? The first artist signed by Interscope? Ever? So was Jimmy Iovine the first guy who started Interscope? But I'm trying to think who was the first one he signed. Well, they approached Tupac and he was basically like, what is this album?

48:20What is this label? I think it's got to be Dr. Dre. no way before that it was um the guy who did uh rico suave oh i don't know you know it's on suave suave rico it was a really bad rap and it was um marky mark you're kidding oh and then they had um primus that's another art act they had yeah this is yeah primus primus are there are they the ones they did the south park theme is that that i didn't know i thought that was um is that not cake is that south no it's primus okay i know because i did their website for interscope oh That's so funny. So that was what Tupac desperately needed a record deal.

48:58Nobody was interested. Atron Gregory, Digital Underground's manager, was shopping it, and Interscope comes along. And it's like, well, what have you done? We did Rico Suave, we got Marky Mark, and we got Primus. And it's like, I'll take it. I'm in. You know, like, all right, that's cool. Somebody wants me. Well, they were owned by Time Warner, too, at the time. So they had the big company behind them. Yeah, true. They did have the money behind. Until Time Warner spun them off because of, in part, Tupac. Like, you know, the violent lyrics, there was the whole Tipper Gore thing going on. Well, it's also still confusing.

49:34I still find it confusing, even though I wrote the book, how, like, all right, Death Row put up the bail money for Tupac, but really, Interscope, Death Row was under the umbrella of Interscope. So it was kind of Interscope, kind of Death Row, really in a scope, but they could say it's Death Row. You know what I mean? It was basically all semantical. It was like, Death Row did it. We had nothing to do with this. Tupac's not our artist anymore. He's Death Row's artist. We're just making a lot of money off of it. It's not us. But that's how all these record labels were. None of them, like both Bad Boy and Loud Records, which was the Wu-Tang Clan and Mobb Deep, actually, they were funded by BMG.

50:15So they were all kind of like, it's like these big companies were VC firms funding these startups and not really involved in the day-to-day, and these startups would just do their thing. Yeah, well, I mean, nowadays, it's like everything. Corporate consolidation is one of the deaths of America. You have the owner of the Washington Post, also the owner of Amazon, also the owner of X, giving large swaths of money to the White House, but saying, I'm going to have an independent newspaper. I mean, this is, not to get too deep into it, but in a way, that was the early age of, we're not really involved, but give us some money.

50:49You know, so Interscope, Death Row, Shirt Night, Jimmy Iovine. Yeah, and then you look at how they all protected themselves. So when the whole censorship thing was happening with like violent and, you know, gangster lyrics and so on, okay, Time Warner said, we're wiping ourselves clean of this. We're Interscope's going independent. And all Interscope did was that they got sold to Universal, which at that point was a Canadian company. A Canadian, you know, they had bought a water company combined it with, you know, the Bronfen family bought this water company, combined it with this U.S. entertainment company.

51:22In the middle, they were a Canadian company and they bought Interscope. So it was just all smoke and mirrors. You know, you and I are about the same age and we've been around long enough that like it's very hard to hold on to idealism. And you just see like greed just trumps all. And like this idea like, oh my God, like they all knew what they were putting out with the Ice-T album, like Cop Killer Body Count. They knew what that was. They knew what that was. Of course they knew what that was. They'd heard the lyrics. They thought it would sell really well and it would do great and it would be this thing.

51:55The minute Dan Quayle catches onto it and George Bush catches onto it and it becomes a public outcry, oh no, it's not ours. But they're still reaping profits off of it. You know, and like, the truth is they should have never pulled back from the beginning. They should have just stood by their artist and endured because Ice-T was a legit artist. He wasn't a joke, but it sucks. Well, Ice-T now is more known for whatever it is. Law & Order. What's the show he's in? Yeah, Law & Order. He's had an amazing career. Icy is had an amazing career. I love Icy. I've been on his podcast. He's a great guy. I was sorry.

52:27He said something about Tupac. I didn't actually interview him. I wanted to. I didn't get him. He said he was talking about Tupac and his affiliation with Death Row at the end. People are like, was Tupac a gangbanger? He goes, nobody joins a gang at 25. That's ridiculous. He goes, the idea that you're joining a gang at 20. You join a gang when you're 16 and you're kind of recruited and you're young and dumb and don't know what you're doing and you're seeking protection, you're not joining a gang when you're 25. And in a way, that was a little bit of the ridiculousness of Tupac because he kind of started identifying with Mob Piru.

52:58He got a Mob Piru tattoo. He's shouting out Mob Piru. He wasn't of Mob Piru, but he was a symbol of them. And if you're an 18-year-old gangbanger and this hip-hop icon is shouting you out, you're not going to complain about it. But it was always kind of silly that he saw himself, fancied himself a gangbanger, when the truth of the matter is he was this beautiful mind, this amazing poet who was generating a lot of income for a lot of people. Well, I mean, I love the story. I love the book. And it was great to read something new about Tupac after all these years. And it just reminded me of a lot of different things in the book, which I mentioned in the intro.

53:37The book is Only God Can Judge Me by Jeff Perlman, The Many Lives of Tupac Shakur. Jeff thank you so much for coming on the show and talking about Tupac and rap with me it's a great pleasure I do want to say something that bothers me tell me you are four years older than me you have all your hair I have no hair this is some serious garbage and I just want to know I'm going to make an offer to you I will send you the complete collected works of Jeff Perlman my entire baseball card collection my iPhone case and 33 stamps if you're willing to swap hair. Well, you have to tell me in detail the condition of all the baseball cards.

54:19Ah, damn it. It's like 150 Mike Greenwell rookie cards. So I don't know if that interests you. Not as much, but you know, we could talk. It depends on the stamps too. Why didn't you collect comic books? I would have done this for comic books. Ah, wrong. I was all baseball cards. Maybe next time. Well, thanks a lot, Jeff. I appreciate it. Thanks for having me on. Very fun. Appreciate it.

54:54This November, action is free on Pluto TV. Go on the run with Jack Reacher. Every suspect was a train killer. Then buckle up for Drive, World War Z. Every human being we save is one less fight. And Charlie's Angels. Damn, I hate to fly. Launch into sci-fi adventure with the fifth element and laugh through the mayhem in Tropic Thunder. What is going on here? All the thrills, all for free. Pluto TV. Stream now. Pay never.