BOBBYCAST: Is Bobby Wrong For Being Mad at This Country Artist?  + Jeff Pearlman Discusses What He Learned About Tupac While Writing His Book + Why Tupac Died Broke + The Process of Interviewing Over 650 People for the Book

Summary

Bobbycast: Is Bobby Wrong For Being Mad at This Country Artist?

Featuring Jeff Pearlman — What He Learned About Tupac (October 17, 2025)

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Overview

This episode of the Bobbycast, hosted by Bobby Bones, dives into two distinct but compelling discussions. First, Bobby shares candid stories from his experiences with country artists who reach out for favors, exploring themes of authenticity and the challenges of professional boundaries in the music industry. The main segment features acclaimed journalist and author Jeff Pearlman, who has written a new biography about Tupac Shakur. They explore Tupac’s complex life—his roots, insecurities, artistry, financial troubles, infamous feuds, and lasting legacy—while also delving into the grueling process of interviewing over 650 people for the book. The conversation is rich with insights, notable anecdotes, and memorable quotes.

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Bobby’s Opening: Navigating the Music Industry and Artist Relationships

[01:43–20:01]

• Fan Interactions & Misidentification:
  Bobby recounts a humorous story of being waved at by teenagers who mistake him for Johnny Knoxville.

  • “The kid in the backseat goes, ‘hey, big fan... You’re Johnny Knoxville, right?’” – Bobby Bones [04:19]

• Artists Requesting Airplay:
  Bobby opens up about receiving frequent DMs and texts from artists seeking airplay or influence. He clarifies his real power is limited—he mainly picks one song per week for a national show and curates the “Women of iHeart Country” segment.

  • He expresses preference for direct requests rather than manipulative “warm up” messages.
  • “I respect that so much more … it was honest.” – Bobby Bones, on straightforward requests [09:17]

• The Uncomfortable Side of Industry Hustle:
  Bobby describes the discomfort when artists fish for compliments instead of real feedback.

  • “If you ever tell an artist what you think about something ... they're not looking for general feedback.” – Bobby Bones [10:19]

• Boundaries and Disappointments in Friendships:
  Bobby details a falling out with a country artist friend who abruptly canceled on a charity co-headlining slot under false pretenses (vocal cord “surgery” turned “rest,” when in reality, none of it held up).

  • The charity incurred substantial extra costs to replace the artist.
  • “The shadiness of it all felt weird and so negative ... So I’m going to relax them from my friendship group.” – Bobby Bones [16:49]

• The Clique Culture of Nashville:
  Bobby reflects on the drama and exclusion in Nashville’s music community, likening it to high school.

  • “This town is the most dramatic town, too. It is. It’s easy to say. It’s so fake, but it’s just like high school.” – Bobby Bones [17:24]

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Interview: Jeff Pearlman — Tupac’s Life, Legacy, and Biography

[21:56–65:40]

Understanding Tupac’s Insecurity and Drive

[21:59–27:07]

• Roots of Insecurity

  • Jeff traces Tupac’s insecurities to extreme poverty, an absent and addicted mother (Afeni Shakur), and childhood experiences of rejection and shame.
  • “...this background of rejection, poverty, sort of embarrassment, shame, I think fueled a lot of what he was—for good and probably for bad too.” – Jeff Pearlman [22:25]

• Performing Arts & Auditioning

  • Tupac’s boldness, even as a youth at the Baltimore School for the Arts: “He just knows he’s going to nail it.” [23:19]
  • Early performance at the Apollo at a Jesse Jackson fundraiser was a lightning bolt of visibility.

• The Drive to Be Seen

  • Tupac’s need for attention eclipsed even money or love, according to people around him.
  • “The one thing everyone who knew Tupac from the beginning to end fed Tupac more than love, more than money, more than cars, was attention. Being looked at, being seen, being heard.” – Jeff Pearlman [26:06]

The Genesis of Tupac as a Rapper

[27:07–28:52]

• Rapping began in New York on the stoop, then blossomed in Baltimore.
• Anecdote: Audaciously trying to get Salt-n-Pepa’s manager, Herby Love Bug, to listen to his rap at a hotel.

Reporting Process — 650+ Interviews and the ‘Brenda’s Got a Baby’ Story

[28:52–36:02]

• Jeff usually expects to interview 400+ for a biography; for Tupac, he conducted 652 interviews.

  • “To me, in my mind, if you don’t clear 400 people, I interviewed 652 for this book.” – Jeff Pearlman [29:04]

• A Reporting Miracle: Finding ‘Brenda’s Baby’

  • Tracking down the real-life inspiration for Tupac’s “Brenda’s Got a Baby”—now a 33-year-old man named Devon—and orchestrating his reunion with his mother.
  • “She has his name tattooed on her arm…they’re just hugging and crying and they talk through the night.” – Jeff Pearlman [35:16]

Truth, Memory, and the Challenge of Biography

[36:10–39:57]

• Dealing with Contradictory Stories

  • Jeff describes methods of cross-checking facts and weighing reliability, especially after the subject’s death.
  • “People who had five minutes with that person spent hours with that person.” – Jeff Pearlman [38:23]

• Accepting Limitations

  • Addresses the inherent flaws of biography—can’t be in someone’s head, have to trust but verify stories.

Tough Truths: Rape Accusations and the Biographer’s Responsibility

[39:57–44:44]

• Jeff reveals two separate rape accusations against Tupac.
• He tracked down the rarely-known LA case’s police report and interviewed the anonymous alleged survivor, seeking the truth regardless of whether it protects or tarnishes Tupac’s legacy.
  • “I feel responsibility to biography more than I respond…to pleasing fans and selling books.” – Jeff Pearlman [42:01]

Cultural Context: Writing About Tupac as a White Author

[44:44–45:42]

• Jeff candidly addresses outsider status, noting he wanted the most comprehensive, fact-driven Tupac book rather than a fan’s view or essay.

Biggie vs. Tupac — Sound, Culture, and “Guttural” Power

[45:42–47:27]

• Jeff contrasts Tupac’s “guttural” delivery (as described by Shock G) with Biggie’s technical brilliance:
  • “Biggie was a great rapper...brilliant lyricist. His delivery was flawless… But with Tupac, he was able to relate to people and make people feel what he was saying, not just by the words…but by the way he said it. He was very unique in that regard.” – Jeff Pearlman [47:10]

The East Coast-West Coast Feud & Tupac’s Shooting

[47:27–52:14]

• Quad Studios shooting framed as the start of real animosity between Tupac and Biggie:

  • “Tupac at that moment, forevermore believes that either Biggie was directly responsible for it...” – Jeff Pearlman [48:31]

• Who Shot Tupac?

  • No definitive answers—possible suspects include Haitian Jack.
  • Fascinating detail: The EMT who treated Tupac at Quad Studios believes Tupac shot himself in the groin, based on wound examination [49:34–51:42].

Money Troubles and Suge Knight

[54:02–61:59]

• Growing Perspective through Writing:

  • Jeff was deeply moved by hearing Tupac’s sister describe their profound poverty.

• Suge Knight’s Manipulations:

  • Pearlman considers Knight in a villainous trio with Don King and Donald Trump.
    • Story: Suge ‘gifts’ Tupac a car he technically doesn’t own; Tupac realizes he possesses next to nothing, despite outward appearances.
    • “My entire life is controlled.” – Pearlman quoting Tupac [57:07]

• Tupac Died Broke:

  • Despite fame, he had less than $200K, little property, and most assets were leased or tied up by Death Row.
  • “He just never had a great stream of income coming to him, just period and all.” – Jeff Pearlman [61:12]

• Estate Wealth After Death:

  • The Tupac estate now profits far more, a point Jeff finds deeply ironic and possibly objectionable.

Pearlman’s Process — And Lighthearted Wrap-up

[62:27–65:38]

• Jeff describes his chaotic writing process, literal “crack den of paper” [62:50].

• Humorous final questions: Bobby asks if Pearlman wanted to try crack due to deep research on Tupac’s life (no!), but Pearlman admits interest in someday trying Hennessy and a blunt instead [63:24].

• Pearlman shares he became more of a fan after the book:

  • “When you learn about what someone went through, the hardships, the troubles—the highs, the lows…I think it has to make you more of a fan because you can appreciate the struggle.” – Jeff Pearlman [64:33]

• Next project: Memoir about early Nashville journalism career, possible Lakers book [65:05].

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Notable Quotes & Moments

• “If you ever tell an artist what you think about something…they’re not looking for general feedback.” — Bobby Bones [10:19]
• “I feel responsibility to biography more than…I do to pleasing fans and selling books.” — Jeff Pearlman [42:01]
• “People don’t understand what you have in me… You don’t see it, but I see it.” — Jeff Pearlman on Tupac’s self-belief [23:19]
• “Suge Knight, to me…would be him, Don King, and Donald Trump. Guys who just take advantage of people.” — Jeff Pearlman [55:19]
• “He just never had a great stream of income coming to him, just period and all. Again, all the stuff he, quote, unquote, owned—he actually only owned one car. Every other car he ever had was leased.” — Jeff Pearlman [61:12]
• “When you learn about what someone went through...I think it has to make you more of a fan because you can appreciate the struggle.” — Jeff Pearlman [64:33]

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Timestamps for Key Segments

• Bobby on country artists hustling for airplay: [04:19–11:00]
• Artist friend backs out of charity, honesty in relationships: [13:26–18:15]
• Intro to Jeff Pearlman: [21:56]
• Tupac’s roots, insecurity, drive: [22:25–26:06]
• Brenda’s Got a Baby real-life story: [29:34–36:02]
• Addressing rape allegations and biography’s duty: [39:57–44:44]
• Biggie vs. Tupac artistic comparison: [45:42–47:27]
• East Coast-West Coast feud: [47:27–52:14]
• Suge Knight’s impact and manipulation: [55:19–57:33]
• Tupac’s financial struggles and estate: [61:12–62:27]
• Jeff on the emotional result of writing the book: [64:33]

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Conclusion

This episode of Bobbycast is a nuanced, honest examination of both the music industry’s internal politics and the complex legacy of Tupac Shakur. Bobby’s introspective stories about boundaries, honesty, and professional disillusionment dovetail into a fascinating, in-depth interview with Jeff Pearlman. Pearlman's account provides not just a window into Tupac’s legendary—and deeply flawed—existence, but also rare insight into the painstaking construction of biography as art and record. The episode is filled with memorable stories, sharp observations, and a resonant message about the value of truth over myth.

Transcript

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Hey everybody. Just driving in back to my house and there's like this white BMW that was right next to me driving on the road, but it was going like 45 miles an hour. It wasn't like a highway or anything. And these four kids started to wave. And if I'm in a car and someone starts to wave at me, there are a few things that can be Number one, it can be that I have a flat tire. That's happened before. Number two, it can be that my gas cap is hanging out because it is on like a little plastic thread that keeps it attached to the car. That's happened before. It could be that they're fans of the show now, being that they're 17 to 19 years old, I probably don't think they're fans of the show if that happens. Probably a little too young at this point. But they're waving, they're waving. I'm waving back. And also I have a pretty cool car and so sometimes it's that. And so I Roll my window down and slow down a little bit because I don't want to hit the kids. I don't want them to hit me either. And the kid in the backseat goes, hey, big fan. I was like, oh, cool. It is one of those times. And he was like, you're Johnny Knoxville, right? No, I was like, I'm not Johnny Knoxville, but thank you. So I wonder if one time in his life, because Johnny Knoxville is actually famous, but I wonder if one time in his life Johnny Knoxville has been approached and someone has said, like, hey, you, Bobby Bones. Just once. But, yeah, that happened on the way here to do this. I've been the last couple days, I don't want to say dealing with, because it's not really anything significant, but. And this has happened a lot through the last 10, 11 years of my career where I will get DMs or texts from artists, and it will always be kind of like a warm up, A warm up before they ask. And the thing is, I really can't do much for them, meaning I don't really program music, which is why when people are like, you're what's wrong with country music? I don't really have anything to do with country music as far as putting it out there. There was a time in my career five or six years ago where I was playing a bit more music, but I don't program music. I literally program two things. One, the national countdown on the weekend, but not the actual countdown that's determined by spins and radio stations all across the country. I play one song, I pick the spotlight artist of the week, like, I do that. And that's a significant spin, I guess, because pretty much every city in the country plays that. But it's only one time, one time on the weekend. The other thing that I do, because I put it in my contract, is the Women of I Heart Country Show. So the quick story of that is six, seven years ago in my contract, when I had a bit of leverage, I said, hey, I want one hour every weekend to just play female songs on every one of our stations, which is like 200 plus stations. And at the time, I think everybody thought that was a little weird because they're like, you're not even a woman. And, you know, candidly speaking, that's true, I'm not a woman. But it was very much the beginning of, hey, why aren't there as many women being played on the radio? And so I wanted to be out in the front of that. I already was. But because I'm a dude you kind of don't get the credit. Wasn't really looking for the credit, but like, when I would tour, I had all, for the most part, female openers. I was constantly having female guests on the show that weren't. So I was already doing my part, but I really wasn't doing anything national programming wise that was consistent. And so I said, hey, give me this hour. Because I wanted to give female artists a bit of a. I don't know if I should share this, like a bit of a spike on the chart because it was a pretty heavy play on that show. Like, I'd play a couple songs from new artists, they'd get a big spike. Program directors would see they got a whole bunch of spins and they'd go, oh, maybe this song is good. Give it a listen. And it really didn't change, like the total outcome of a record. But maybe it gave some of those artists a chance earlier. So that was the whole idea behind it. So I have an hour and I program that. And you're gonna see my point here. And if I want to, like, they call it spike a song in, I can do that, which is just on my show. If I decide I want to play a song, I'll play a song. But I really don't want to be the song guy because with that comes everybody wanting you to play their songs, and that's just not me. And again, there was a time when I was breaking songs like crazy. If it was Buy Me a Boat or Girl Crush or I Love this Life Low Cash, there's six or seven of those songs that I played a whole lot when nobody else was playing, which really moved them up the chart and then gave them really strong ammunition to go other places and go like, look, it's getting a lot of play. I stopped doing that because, one, I don't want to base my career on music I don't make. So it's been something that I occasionally do, but I don't really put any significant time, thought, effort into it. That doesn't mean that people don't hit me up thinking either. A, I have more power than I actually do, which is not a whole lot. I guess I have a little sway with the president of iHeart Country. I mean, I've worked with them for 13 years. I know him very well. But, you know, anyway, I get the warm up from these artists and it'll just be a reach out, out of nowhere to be like, what's up? How's it going? How you been? And I can tell immediately when the warmup is happening because I know the warm up is going to be possibly a day, a day and a half of, hey, cool, we should hang out sometime, whatever else. And then bam, there'll be a file in my text message. And, hey, if you don't mind, would you check this song out and tell me what you think of it? And when an artist asks you what do you think of a song, they really don't want your opinion unless it's good. They really just want you to go, oh, it's excellent. I'd love to play it. And if you don't say that, then they're gonna ask, hey, is there any way you can play it? So I've been getting the warm up from a couple artists, one through text, one through dm, around the same time, ironically. And I know them, but I'm not friends with them. Now at the same time, there's another artist that hit me up a couple of weeks ago who I don't know either. I don't know how they got my cell phone number. I mean, I don't really care, but they just were like, hey, this is so. And so I got this new song out. Would you listen to it? And if you like it, maybe you'll consider it. I respect that so much more. And I don't think I ever played it, but I don't, like, have a bad taste in my mouth just because it was right to the point, like, it was honest, where the other people are like, let me give you a little massage. Let me tickle you around the waist. Okay, that'd be $500. It's kind of, I guess it's not really the same, but that's what I've been dealing with. And I just know when it's coming. And so I guess I can be a little cold when I see it coming because I don't respond. And one of them, they were DMing me. And I knew what it was because it had already been like three messages. And this has probably happened to me before at some point with the same artist. And so I didn't want them to see that I had read their dm, so I just would delete the message. And then like clockwork, the next day, boom. Got a new song. Would love for you to check it out. It also sucks because it makes me not trust anybody. And the thing is, I don't really have the power. I don't have power to, like, shape a career. Like, I can put you on the show or the podcast, and that's more of a macro versus a micro thing. Because if you come on the show or you come on the bobbycast, usually that translates into, like, social media. You know, the podcast does really well now. It's probably the second biggest country music podcast. The bobbycast is behind our show, which is number one. So there is some significance to that, but I. I just don't have the power for the music. But then it has me. Not like the artists who do that, which it isn't fair because I know it's their job to hustle in a way, but I don't like the grossness of it. Like, I did like, the guy who I didn't really know that hit me up and was like, hey, I got the song. Listen to it, and if there's any chance you consider to play, that'd be awesome. And there was no, like, question. There was no, like, what do you think about it? Because if you ever tell an artist what you think about something, a song, and you're like, yeah, I don't really.

Think it was that good. It wasn't for me.

I wouldn't say that, because I know that's not what they're looking for. They're not looking for general feedback. That's happened a couple times with friends, and they're not even asking, like, hey, is it a good song? They're going, hey, do you think if we took this to the vice president of programming that they would like it, do you think? And those answers I can give, but I don't really want to, like, not like artists, because it affects other decisions. Like, there are times where it's like, hey, it's an interview coming up with this person. Do you want it? And it's been kind of gross like that. And I've just been like, I don't think so. Like, I don't want to be around something that makes me feel weird or if I feel like somebody has, like, ulterior motives with something. So that's been the last couple days that, and my tooth. My tooth here is still broken. I get a lot of messages from you guys that are like, hey, why is your tooth gone? And my wife especially, who calls it tiny, she's not a fan of it. My dentist actually just texted me because I think he saw it online as well, and he's like, hey, come in. Let's fix your tooth. And I kind of decided that I wasn't going to fix my tooth until I had a reason to fix it, meaning if I was going to go and do some television work of some Sort. So my thing was I'll fix it when it needs to be fixed because I don't really like going to the dentist, although my dentist is good. But you see here, it's still gone, it's still jagged. But at this point, I did pay for it already, so I should go and get it fixed. I'm hoping that this recording here, which you're watching either on YouTube or the audio, sounds good. I'm trying it a different way, so hopefully it doesn't look or sound too weird. And if it does, don't worry. Done. I'll stop doing it this way. I get a lot of response to that YouTube video that I did on artists that don't like each other. And if you go over onto the YouTube page, which the YouTube page is different than the Bobby Bones show YouTube page, this is obbybones channel. I probably should just change it back to the Bobbycast. But over on the channel, I did all these artists that had feuds and then people that I have fought with, I'm not even gonna say feuds, because who cares about me? Over the years and I keep getting messages and DMs like, are you feuding with anybody now? I'm really not, because, like, it's mostly energy and time waste. Like, it's all a suck of time and energy. And also I just kind of, at this stage of my life, cut people out if that relationship isn't a net positive for both of us. And I think relationships should be romantic relationships, friendships, any relationship should be a net positive. That doesn't mean it's always going to go good. As a matter of fact, the longer that you're in them, if they are substantial, it is not going to go good. But at the end, when you tally it all out, you should actually be a little better because of the relationship. I can give you a story. And I'm not beefing or feuding with this person just because I've chosen not to.

But.

And I'll keep the timeline out, it was. I would have considered this person a friend. And so I was doing a charity event and the charity said to me, because we weren't getting paid because it was for charity, hey, do you have anybody that would want to hop on and do this charity event with you, like a co headliner? And so I called this person friend of mine and I was like, hey, here's the charity. I think it's something you might want to be involved in. And they were like, yeah, sounds great. And so we had signed up to do this charity event, like eight months ahead of time. Well, a few weeks to a month leading into it. And again, I would have said I was actual friends with this person, not just buddies that you see or people that come on the show and you're like, what's up, buddy? I haven't seen you in a while. But you're really not friends. Like, not acquaintances friends. Like real friends. I would have considered us to be right there at that level. And about a month before, I get a call from this person's manager, which is weird. And my manager gets a call from this person's manager, which is weird because I know the person. Like, I've spent significant personal time with the person, and they go, hey, they gotta back out of the event. They have to have, like, vocal cord surgery. And I'm like, dang, that sucks. My initial reaction is, dang, that sucks. Because anytime you gotta have any surgery, that's.

That's.

That's not fortunate. Secondly, if you're a singer and you have to have vocal cord surgery, that's gotta be scary as crap. But I remember thinking, why didn't this person who's my friend call me to tell me? Because I know they're still talking. I just had seen them on social media that day. And again, I really felt like this was a friend. But so I thought it was weird that the manager called me. By the way, if you have to, like, get out of something for any reason, if it's like a personal reason, a health reason, I don't care, Just say it. If your grandma's sick, no problem. Also, it's not my charity event, so just like, be for real about it. I guess my whole point to this is I hate when people aren't for real about stuff. And so I'm like, okay, man, that sucks for them, first of all. And second of all, for this charity event that I am co headlining, because.

I was doing stand up, they were.

Doing music, and so there's just a few weeks left and I have to call the charity. I had to call the charity and be like, hey, this person's not doing this anymore. And so, like, so we had to find somebody new. And they ended up having to pay a pretty significant amount of money to get another person. And that's money that would have gone to the charity, but because it was so last minute, they had to pay a bunch. And that sucked for them. Didn't suck for me because whatever. And then I find out the story changes from vocal cord surgery to they needed to be on vocal Rest.

Same thing.

Had you just called and said that from the beginning, I think that I'd have been like, oh, I totally get it. Like, you can't play in a charity celebrity softball game if your elbow. If you need elbow rest because you've heard it, do it. There's just common sense things. So you could have said that, but it started with surgery and that they didn't call me. So I was pissed that the person didn't call me.

I was like, why?

And so after I shared my frustration of. Especially when I found out that they didn't even need vocal rest, they were then on a television show after that, and they had no surgery. I don't really quite know why they wanted out of the event, but they were so dishonest about everything that I thought, I don't really the kind of person that I want to have in my life. And I haven't really spoken to them in, like, two years. And as I say that out loud, I don't love it. And I did get a call way after the fact, but it was only after the fact that I was, like, so irritated that they were so dishonest. One it was surgery, then it was vocal rest, and then they need vocal rest, but they're still gonna go and do a television. It wasn't even my charity. It wasn't even my money. I had to pay for the extra person. It was just weird they didn't call me. So the shadiness of it all felt weird and so negative that I thought, if they can do this at this point, they can also do this at a different point. So I'm gonna go ahead and. And I'm going to relax them from my friendship group. And by the way, I don't have a big friendship group. I really don't do anything. I work. I got, like, four people I hang out with and all good. So they're not missing me in their life. I'm not missing them in their life. But when it comes to, like, shadiness, I don't have any room for it. When it comes to drama, I don't have any room for it. Oh, especially drama. I'm not a dramatic person. This town is the most dramatic town, too. It is. It's easy to say. It's so fake, but it's just like high school. If I cared about having friends in the artist community, I think I'd probably stay irritated and upset about it. But it is so cliquey, and it's groups that want it to be known that other people can't be in their group. And it's like artists and wives. And it's kind of funny to watch from the outside, especially when you see, like, pictures being posted on social media because you know these people and you know why they're doing it. But I think back in high school, it bothered me because I wasn't cool. Now I kind of am glad I'm not cool because I don't really have an interest to be parts of some of these things. And I hope wherever you live, I know this is happening, too. It's not just a Nashville thing. I think this is a every. And Nashville's not a small town, but the music, the performer community is a pretty small community here. And it happens here, too. So just know that it happens here, too. So, yeah, that's what's up. That's the check in here, I think. Now we're going to get over to the interview that I did with Jeff Pearlman and we talk about Tupac. He wrote a Tupac book. It's very interesting. Even if you're not really a Tupac fan, I think it's interesting to hear the stories about it he has written. I think it had 10 number one bestsellers. So we're gonna get to that. I'm hoping you're not hearing all the text messages come through my computer as I've been recording this. This has been a trial run and thank you, everybody, and I will talk to you on the other side of this.

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[Asma Khalid]

America is changing, and so is the world.

[Tristan Redman]

But what's happening in America isn't just the cause of global upheaval. It's also a symptom of disruption that's happening everywhere.

[Asma Khalid]

I'm Asma Khalid in Washington, D.C. i'm.

[Tristan Redman]

Tristan Redman in London, and this is the Global Story.

[Asma Khalid]

Every weekday, we'll bring you a story from this intersection where the world and America meet.

[Tristan Redman]

Listen on BBC.com or wherever you get your podcasts.

[Jacob Goldstein]

This is Jacob Goldstein from what's yous Problem? Business software is expensive. And when you buy software from lots of different companies, it's not only expensive, it gets confusing. Slow to use, hard to integrate. Odoo solves that because all Odoo software is connected on a single affordable platform. Save money without missing out on the features you need. Odoo has no hidden costs and no limit on features or data. Odoo has over 60 apps available for any needs your business might have, all at no additional charge. Everything from websites to sales, to inventory, to accounting, all linked and talking to each other. Check out [e-mail]. that's o d o o dot com.

[Bobby Bones]

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And we're back on the Bobbycast.

All right, we have Jeff Perlman on with us, who wrote a book about Tupac. Only God Can Judge Me, the Many Lies of Tupac Shakur. I think as a performer myself, it's all rooted in absolute deep insecurity. I do not look at Tupac from back when I would listen to Tupac. I mean, I guess I do occasionally now, but for the most part, I didn't look him as a super insecure guy. Like, what did you learn about him in that element as a performer? Was it based, rooted in insecurity at all?

[Jeff Pearlman]

I think it was based more on insecurity brought forth by abject poverty, by his mother's addiction to crack, by spending much of his days living in his youth in Baltimore with rats scurrying up and down the baseboards, showing up at school in thrift store clothing, having bad teeth, not smelling good, girls not being interested in him. Like this background of rejection, poverty, sort of embarrassment, shame, I think fueled a lot of what he was for good and probably for bad too.

[Bobby Bones]

I found that with people that come from not a lot, I would even include myself a bit. There is that there are two ways to go. One, like, you want to prove everybody wrong, and so you're gonna stop at nothing until you do. Or what's, you know, actually a lot easier to do is just fall into it and fall into that same system. What was Tupac's relationship with those choices?

[Jeff Pearlman]

Oh, you know, he, he, he, he grew up in New York, moved to Baltimore. He spent his freshman year at Dunbar High School, then found out about the school, the, the Baltimore School of Performing Arts, and he had to audition and Tupac had nothing. He wore two pairs of pants. He would rotate his pants. He wore the same crappy thrift store shoes. Everything about him was poor and sad and small. He was small and kind of Spinely. And he shows up for this audition, and he just knows he's going to nail it. Like, he knows. He doesn't think he's going to nail it. He knows he's going to nail it. And he walks into the grand ballroom of the Baltimore School for the Arts, and the four teachers are all sitting there, four white teachers, very stern. And he does a monologue from Raisin in the sun, and the teachers, when he's done, stand up and applaud for him. And he gets a spot in the School for the Arts. And he knew he was going to. Like, he was so driven. He knew he was bigger than what surrounded him. He knew he was more powerful. He knew he had this thing in him, like he always knew. And I think everything going on around him drove him to be bigger. It was almost like this thing, maybe you've gone through yourself. You people don't understand what you have in me. Like, you don't see it, but I see it, you know, like, he showed up and he's on the stage, and he knew it. He just knew it. And I think that was all driven from what he came from.

[Bobby Bones]

Was there anything around him that led him to believe that there is a reality in performance? He was on the east coast, so, you know, you're kind of close to New York. Like, how did he know if it wasn't a tangible thing?

[Jeff Pearlman]

Well, it kind of was. So he was in a. He was in a theater company in New York before he moved to Baltimore as a young teen. And he actually performed at the Apollo Theater at a Jesse Jackson presidential fundraiser in 1984 in a raisin in the Sun. And he had this moment. He was the first person on stage for the performance. He's in the Apollo Theater. It's filled with people. Jesse Jackson is there. And it's this moment where everything is quiet and you look out and they're all looking at you. And I do think there's something really, really profoundly true about people who always feel ignored and underappreciated, having everyone look at you and have the focus on you and you feel seen. So I would say that moment in particular was a real jolt to him becoming what he became.

[Bobby Bones]

And again, just getting into, like, the fundamental parts of him as a performer, I found that a lot of performers are, in essence, searching for love because they didn't get it at one point in their life. And. And that, you know, performing on a stage, performing behind a microphone, like you're searching for adulation, for love to compensate for what you did not have growing up. And I. I think that's what you're saying. Would that be kind of the reason he did any performance at all?

[Jeff Pearlman]

I think so. I mean, it's really interesting. His mama, Fanny Shakur, was a very famous Black Panther, represented herself in the famous Panther 21 trial when she was pregnant with Tupac, was this civil rights icon. And he. She. She was his hero, his absolute hero. And then she became an addict. And he's watching this woman he loves also fall off into dis. A state of disrepair. And all he wants is something in his life that feels real and positive. And the thing he gets is attention. His whole life. The one thing everyone who knew Tupac from the beginning to end fed Tupac more than love, more than money, more than cars, was attention. Being looked at, being seen, being heard. I think that's a really powerful driver for a lot of athletes I've written about, I'm sure for a lot of musicians and people you've interviewed as well, this need to be seen and heard. And I think he was a guy who was ignored much as. As a child. And all of a sudden, people are lavishing attention on him.

[Bobby Bones]

Then when did it turn to hip hop? When did it turn to I can be a rapper?

[Jeff Pearlman]

I mean, he started. He started rapping when he was in New York on the stoop in the Bronx, like his mom, his aunt Glow. All these people would go be upstairs in the apartment smoking weed and talking, and all the kids would be on the stoop, and they're all listening. This is in the Bronx in New York city in the 1980s. They're all listening to Curtis, Blow, Houdini, you know, Sugar Hill Gang, Run dmc. And he's just rapping on the steps. And he moves to Baltimore, and he teams up with a guy named Mouse, and they start rapping. They form a little rap group. And he has this moment, this great, great moment. He's a student in Baltimore, and there's a. A concert coming to the Baltimore arena, including Salt and Pepper. And Salt and Pepper's manager is her Herby Love Bug. And they go to this show, Salt and Pepper, and it's Heavy D. It's different performers, and they know the performers are all staying at a comfort in near the Days in, near the Baltimore Arena. Before the show ends, they decide they're going to go to the Days in and show Herby Love on what they could, but what they could do. So they rush and they see him walking in, and Tupac walks up to him too. That's a teenager, hasn't done anything. Bad haircut, shitty crappy clothes. Excuse me. And he's like, yo, Herbie, Herbie, this is my crew. Can you. Do you want to hear us sing? Do you want to hear us rap? Blah, blah, blah. He's like, yeah, okay. And he's like. He's like, but I gotta go up. And he never came back down, right? And Tupac is waiting and waiting and waiting. He's getting more mad and more mad. And finally he's like, we're going upstairs. And they spend the night hanging out with the rappers outside their room. Like, he just had that audacity about him. You're going to hear me. Someone's going to hear me. So throughout Baltimore, he's rapping. And then he moves to Marin City, and that's where it takes off. In California, when you do a book.

[Bobby Bones]

Like this, obviously you want to talk to the people that knew Tupac and the people that knew. The people that knew Tupac.

But when you start, how many people.

Do you think you're going to have to interview? And does that list expand as you're going?

[Jeff Pearlman]

I usually consider you got to go at least 400 on a biography. To me, in my mind, if you don't clear 400 people, I interviewed 652 for this book. So it was. It was deep. And I got. I had extensive time with his sister, with the people who formed him along the way, his different managers, performers, cousins. I had a moment, like the greatest reporting moment in my career came out of this book. It's a story. I don't know if you want me to tell it or not. Yeah, no, tell.

[Bobby Bones]

Please do.

[Jeff Pearlman]

Okay. So do you know the song Brenda's Got a Baby?

[Bobby Bones]

I do.

[Jeff Pearlman]

Okay. Tupac is filming Juice in New York City. It's 1990. And every day when he was growing up, he would read the New York Times, his mom would read him the newspaper. It was very important to her that he knew what was going on. So every day while filming Juice in New York, they would bring a pa, would bring him a copy of the New York Daily News. And one day there's an article and it's Cries in the Night and It's about a 12 year old girl who's raped by a cousin, deliver the baby without anyone knowing she was pregnant on the bathroom floor, wrap the baby up in an odd job bag, plastic bag, threw the baby down the trash chute, and that was the inspiration. Tupac reads this article, says to Omar Epps, I gotta go in my trailer. I gotta go. My trailer. Sits in his trailer, writes the words to Brenda's Got a Baby. Brenda's got a baby. Brenda's barely got a brain. The damn shame the girl can hardly spell her name. So this song is his first big song. And I decided I really wanted to find the baby who was thrown down the trash heap all those years ago, who inspired this song. And I work with a genealogist named Michelle Suli, who's just incredible. And I told her about this, and one day, she. She's like, I think I have a number for this guy. His name's Devon. I. I text because no one answers their phones. I text this guy Devon, and I'm like, hey, by any chance, is this you? And I attach the article. My name is Jeff Pearl. He writes me back. He's like. He's like, call me tomorrow. Long story. I go to Las Vegas. He lives in Las Vegas. He's 33 years old now. He was the baby at the time. He was the baby who was thrown down the trash Heat by Tupac. I'm talking with him about it. Amazing story. Basically, he was adopted. After he was thrown down the trash heap, his. His parents moved to Las Vegas. They died. He does an Ancestry.com search. It's not that long ago. All these tentacles point back to the noble Dr. Ali Housing projects in Brooklyn. He reaches out to different relatives. They're like, we've been looking for you for years. We didn't know what happened to you. Also, are you a fan of Tupac? He's like, I love Tupac. They're like, do you know the song Brenda's Got a Baby? Of course I know the song Brenda's got a baby. We think you're the baby, and Brenda's got a baby. He flies back to the housing projects where he was born. They show him the shoot where his mom threw him down. He poses with it. He meets all these relatives. It's this beautiful moment. He hasn't seen his mom in a gazillion years. Like, shortly after he was born, we decide we have to find the mom. My genealogist, Michelle Sully, thinks she has a number. She calls this woman. She goes, is this Janine? I'm using a fake name. She goes, is this Janine? She goes, yeah. Did you have a baby when you were 12 years old? The woman starts screaming, do you know where my baby is? Do you know where my baby is? She goes, well, my name is Michelle. I'm a genealogist. I'm working with Jeff, oh, my God. Do you know where my baby is? She's screaming and crying. Michelle says, I mean, the woman says, I need to. I need to take care of the. She goes, I live in Newark, New Jersey, but I'm. I'm. I'm away because I'm going to see the Red Hot Chili Peppers. And Michelle says, where are the Chili Peppers playing? And she said, in Las Vegas. She goes, your son lives in Vegas? They met that night. Wow.

[Bobby Bones]

The Bobby cast. We'll be right back.

[Asma Khalid]

America is changing, and so is the world.

[Tristan Redman]

But what's happening in America isn't just a cause of global upheaval. It's also a symptom of disruption that's happening everywhere.

[Asma Khalid]

I'm Asma Khalid in Washington, D.C. i'm.

[Tristan Redman]

Tristan Redman in London, and this is the global story.

[Asma Khalid]

Every weekday, we'll bring you a story from this intersection where the world and America meet.

[Tristan Redman]

Listen on BBC.com or wherever you get your podcasts.

[Jacob Goldstein]

This is Jacob Goldstein from what's yous Problem? Business software is expensive. And when you buy software from lots of different companies, it's not only expensive, it gets confusing. Slow to use, hard to integrate. Odoo solves that because all Odoo software is connected on a single affordable platform. Save money without missing out on the features you need. Odoo has no hidden costs and no limit on features or data. Odoo has over 60 apps available for any needs your business might have, all at no additional charge. Everything from websites to sales to inventory to accounting. All linked and talking to each other. Check out Odoo at O D O o dot com. That's O D o o dot com.

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[Bobby Bones]

This is the Bobbycast.

So how does that make you feel this as a person? Like, aside from the book, aside from what we're talking about here, like, that's like, like fundamentally shifting. That's one of those events for them and probably for you as well.

[Jeff Pearlman]

It gives me chills even telling that story right now, having told it several times already, you know, to my relatives and friends, it's an amazing feeling. It's fantastic. It's one of the best. It's the best find I've ever been a part of in my career by far.

[Bobby Bones]

Man, I just questions about that, like, did. How, how, how did the meeting go?

[Jeff Pearlman]

It was great. It was beautiful at first. In fact, she showed up and she hadn't seen the baby. She hadn't seen her son in years and years. She had visitation for a brief period of time after he was born where she was able to see him. And that was. And she shows up. And when they were in the house after she gave birth, they found her, brought her to the hospital, brought the baby to the hospital. They let her hold the baby and name the baby, and she actually named the baby Devon. She gave him his first name and the adoptive parents kept the name. She shows up, they met in a, in a casino in Vegas, in the lobby, and she has his name tattooed on his arm, on her arm. Because she had just always been thinking about him from years and years ago, from decades ago. She tattooed his. His name on her arm. And they're just hugging and crying and they talk through the night.

[Bobby Bones]

Wow, that's crazy. I mean, if, if that is what comes of the book, like, That's a lot.

[Jeff Pearlman]

100% agree. 100% agree.

[Bobby Bones]

Wow.

Yeah. So as far as Tupac goes, you know, everybody thinks about him as being a West coast guy, which isn't. I, I've known that that's not where he grew up, but that's where he became the Tupac that we know. Did Tupac consider himself a West coast guy?

[Jeff Pearlman]

Yeah, he definitely did. Over time he did. He basically when he, before his senior of high school, he went two years at School for the Arts in Baltimore and he moves to Marin City and he's very upset about it. And Marin City he lives in, it's called the Jungle. And he basically lives in public housing in Marin City. His mom dives Heavy Duty in the crack. And while there, Tupac moves in with a kid his age named Demetrius Striplin, who's a DJ and just a nice guy who takes him in. And during that time period, Tupac is writing raps non stop and he's listening to Too Short and Ant Banks and all these Bay Area rappers and he's absorbing it. But he has a moment near where he lives. They would have these rap battles and he gets his ass kicked in a rap battle one day by this guy named Tack who's like 13 year old rapper and he just demolishes Tupac. Tupac goes back to the apartment and he's devastated and he vanishes for a week. For one week, nobody sees Tupac. And basically he spent the week hanging out with the biggest crack dealer in Marin City. And he asked a guy if he could follow him around. His name was Bobby Burton. If he could follow him around and just take notes about what it is to deal crack and to be a gang banger and to be a badass in the inner city. And he comes back and he has a songwritten called all in the Days of a Criminal. And he wraps it for his roommates. Immediately they're like, whoa. And it really did show. The guy was a student. And actually, it's one of the joys of this book was I spent a lot of time with the old crack dealers of Marin City. And, like, I went to a diner with Bobby Burton and his grandson, and this guy was the most terrified, terrifying crack dealer in Marin City. And we're sitting there eating eggs with his grandson. And it was a very full circle kind of moment for me as a reporter.

[Bobby Bones]

I'm assuming the grandson doesn't know his granddad as that crack dealer.

[Jeff Pearlman]

No, it was a lot of like this. A lot of like. Cover your ears. All right, go listen over there. You go over there for a minute. Great guy, though. The guy was awesome. He was delightful. Yeah.

[Bobby Bones]

When you interview 650 plus people and they give you stories that, well, are exactly the opposite, how do you deal with that?

[Jeff Pearlman]

It's a lot of cross checking. It's a lot of triple checking. It's also a lot of who has a history of being a reliable subject, who might exaggerate one thing that I have found with Tupac, and I'm sure you've seen it also with celebrity young deaths. As the years pass, people who weren't that close to that person suddenly are amazingly close to that person. People who had five minutes with that person spent hours with that person. So it is a lot of, like, checking and rechecking, double checking and just making sure someone says no. This is a person you can trust, a trustworthy person. Telling you someone is trustworthy goes a long way.

[Bobby Bones]

What about the development of truth into, like, hyperbole? And not for any other reason than time. That has to happen too. Right?

[Jeff Pearlman]

Of course. And the truth of the matter is biography is a flawed medium to a small degree. Right. My book before this was about Bo Jackson. Most of what Bo Jackson did athletically wasn't recorded. You know, he was timed running a 41340. I can see the notation for the 413040 in the Auburn log. Do I know for a 1 million trillion percent fact that it wasn't 42340? I don't like part of this is believing what is written and believing stories that are reputable. It's a flaw. There's no doubt. The other flaw of biography is you can't be in the person's head. So Tupac is walking down the street. Tupac is in the MGM grand, and he sees Orlando Anderson, and he goes, punch him. I'm thinking, he's probably thinking, oh, crap, I gotta punch this guy before I know he's thinking about the jets quarterback situation. You know, you can't know. You can't be in someone's head. It's the hardest part of biography, by far, is you can't be in someone's head.

[Bobby Bones]

I would think, too, when you are writing a story on a dead legend, which is what Tupac is, you want to make sure you get the good, the bad, the middle, the background all. But when it's something uncomfortable, like a rape accusation, like, how did you deal with that?

[Jeff Pearlman]

I had something. I haven't even talked about this yet, but, you know, it's in the book I found. All right, so the rape accusation was obviously tough. And I reported it and reported it and reported it, and I found people who were around there and different people. But the interesting thing is, four months before that happened, another woman accused Tupac of rape. It's never been reported before. And I found the police reports that were filed, and it happened at a Club in LA. It was a woman who was celebrating her 21st birthday. I found a redacted police report and then an unredacted police report. So I had all the names, and I found this woman, and she basically, she needed a ride. Hunt. She was 21. She was at a club in LA. She was out with her friends. Her friends kind of ditched her. She had been talking with Tupac and his crew. They offered her a ride home. She was staying with her boyfriend, who was a football player at usc. They, instead of going home, according to her, Tupac, like, we got to stop at the house real quick. He had a house not far.

[Bobby Bones]

Where?

[Jeff Pearlman]

Far away. She said. According to her, she said, just come in for a minute. Just come in. He goes in. She said he had a gun on his. On his, like, bookshelf and said he raped her. And then he said one of his friends drove her home and also forced her to have sex. So she. I got this police report. And I know I have to try to talk to this woman, right? And this was four months before the incident at Nell's in New York City involving Ayanna Jackson. It's four months before I have this police report. I'm writing a biography. I know for a fact Tupac fans do not want to read this.

[Bobby Bones]

Right.

[Jeff Pearlman]

If you're a Tupac fan, you understandably want to believe that Tupac wouldn't have done such a thing, was innocent. But I feel responsibility to biography more than I respond. Feel responsibility to pleasing fans and selling books, if that makes sense. I have this police report, I have the name, I find the woman, I reach out to her. At first she tells me it's all true, but she's like, I, I don't want to talk about it. And when I found the unreal I found a few months later, I reached out to her again and I said, I'm just curious, do you have any interest in seeing the police report? Like, do you want to see it? And she said, yeah, actually I do. And I sent it to her and she called me back. She's like, okay, I want to talk to you because this is making me really mad. And basically what happened is everything she said, she swore happened all these years later. Anonymous. She had no reason to lie or not. Like there was no incentive for her to lie. She's a 50 year old woman now living not at. In California. But she said after, after she filed the report, the officer who was going to decide whether to go, the detective was going to decide whether to follow through with the, with the charges said, why didn't you run away when you had a chance to run away? And she's like, I was drunk and scared. And they're basically like, no, you had a chance to run away and you didn't run away and they didn't pursue it. And she was so mad delivering that that she talked to me at length about it. Now she talked to me anonymously, which is fair because it's a rape case. So that's knowing that he had a very similar incident. There are a lot of parallels between what happened to this woman in la, what happened to Ayanna Jackson in New York. So that's a big part of the reporting of it.

[Bobby Bones]

I would think that the human nature part of writing a biography would be, and I'm glad you spoke on that feeling like you have an allegiance to the biography more than the, than, than the fans of Tupac, that if you're writing about Tupac, you want his fans to buy the book. So I'm sure that there's a part of you that's like, man, if I just don't write about this, I think.

More people want to buy the book.

Because it's just a glowing part of Tupac. I mean, is that an internal struggle that a writer like yourself have to deal with?

[Jeff Pearlman]

And it is not. But I understand why it would be. I, I just, long ago, starting at the University of Delaware and as a news writer at the Nashville, Tennessee, I'm like, that's not how I think. You know, like probably maybe to my own financial detriment, I just don't think, oh, man, I have to. This is going to be. Tupac fans are going to love this. I want a historic record of Tupac. The goal is always, and I'm not saying it's always achieved. The goal is someone reads your Tupac book and they say, well, there's no other reason to write a Tupac book. Like what? There's nothing more. There's no other reason to write a Tupac. And I'm not saying that's real, but that's kind of your goal. And I can't. It's not. I'm not a fan writer. I'm not writing for team beat or BOP or whatever it would be in 2025. I'm just not that guy. So it is what it is.

[Bobby Bones]

You're a white guy writing about a hip hop artist. I don't know. That's. That's weird, huh?

[Jeff Pearlman]

Yeah, yeah. My agent, it's my first non sports book. It's obviously my first hip hop book. Yeah, no doubt about it. My agent was like, are you, do you really think, do you really think you're the guy to write this book? And the truth of the matter is, this is weird, but true. The writer Kevin Powell had on his website for years, next book. A Tupac book. Right. For years. And I kind of just assumed Kevin Powell was going to write this Tupac book and I was just not going to write it. But he never did it. And I wanted the book where 650 people interviewed about Tupac. I didn't want the book why is the greatest rapper of all time or Tupac and me my Wild Adventures. You know, like, I wanted the book about Tupac, so I just, I know I'm white. I come from an outsider's view. I tried to be honest about it and open about it and, and do.

[Bobby Bones]

My best whenever I think about hip hop in the 90s, even late 80s, 2000s, right? Because that was like my time. And I think about the rappers that were, I'd call the best culturally and also, but then the best, like that sounded the best. Like, for me it was always like Biggie always sounded the best. But Tupac meant more to the culture. And I grew up in not a white neighborhood, so I was never like, tupac sounds better than Biggie, but he says more than Biggie.

Although Biggie did say a lot because.

Biggie had stories too, right? Like he's, he's doing his, he's doing his thing. East coast, what are your thoughts on my possibly incorrect narrative?

[Jeff Pearlman]

Okay, I think Shakji from Digital Underground said it perfectly.

[Tristan Redman]

He.

[Jeff Pearlman]

He has passed away, but when he was live, he said a lot of rappers rap. I'm going to paraphrase, he's a lot of rappers rap from the nose, Some rappers rap from the lip, some rappers rap from the throat. He said Tupac rap from the stomach, where it was guttural, you know. And the other, only other rapper, really great rapper who could compare to that is dmx where it's like you feel it and you feel every word. And there's a song Tupac has, it's probably my favorite Tupac song. It's called Shorty Want to Be a Thug. And just about a 16 year old kid who's trying to, you know, gang banger. And you just feel every word of it. Like you feel every word of it. And I think about rappers from who came up alongside Tupac. Biggie was a great rapper. He was a brilliant, brilliant lyricist. His delivery was flawless. It was beautiful. It was almost symphonic and how beautiful his rapping was, but it wasn't guttural, you know. And I feel like with Tupac, he was able to relate to people and make people feel what he was saying, not just by the words, which were powerful, but by the way he said it. I think he was very unique in that regard.

[Bobby Bones]

And the reason that I compare the two, obviously is because the whole East Coast, west coast, and how that tragically ended, how much of that started as wrestling and ended real or was it all real?

[Jeff Pearlman]

Well, it started at Quad Studios and Tupac is going to Quad Studios and Tupac is on trial in New York. And at the same time, an artist named Little Sean is releasing, is putting together an album. And Tupac needs money. You know, true Buck died very. He had less than $200,000 in his bank account when he died. Like he did not have a lot of money. And he has the legal fees and everything's Mounting. And he's going to go to Quad Studios and record a track for Little Sean. And he's getting paid. This is crazy. $7,000. That's how much. Tupac was going to Quad Studios to do a track for some guy, Little Sean. So he. He's going there and he pulls up and he gets out and, you know, he's. He's. He's in the lobby and he gets shot, and he gets. He gets robbed and he gets shot, and he goes upstairs, and there's Biggie and there's little Cease. He was down in the elevator, and these guys are there, and. And Tupac at that moment, Forevermore believes that either Biggie was directly responsible for it, or if nothing else, I'm in New York City. This is your city. How could you. In this building, how could you not know? And I interviewed a lot of guys who are in prison with Tupac at Clinton, and he did not let that go. He held that tight. Biggie did this. I know Biggie did this. That M effort did this. He wrote lyrics about it. He was so angry about it, irrationally, so that when he got out and then he writes, hit him up, obviously, and it just inflames everything. So I don't think Biggie tried visiting Tupac in the hospital. He tried visiting him again at Clinton. Literally called his manager Watani and said, can I. I want to go visit Pac. And Tupac said, no, I'm not seeing that guy. I think Biggie was dumbfounded the whole time. Why am I getting blamed for all this? But Tupac saw it as a certainty then.

[Bobby Bones]

Okay, let's just say it wasn't Biggie.

Who do.

Who do we think it was? Puffy?

[Jeff Pearlman]

I mean, most of the eyes point to. To Haitian Jack, who. Who took Tupac kind of under his wing. He was actually Tupac's muse for above the rim when he played Birdie. And then they started having this growing divide, and Tupac started calling him out as a hanger on. There's a lot, but there's no certainty. There is no certainty. I will say one thing that was interesting, who I did find for the book. So Tupac was shot. It was always noted incorrectly. He was shot three times in the head, in the hand, in the testicles that went into his leg. And for years, there are always these rumors that. That Tupac. That Tupac shot himself in the Boss. And I found a. The first EMT to ever get to Tupac. And he'd never been. He'd never been interviewed before, and he's like, wow, how'd you find me? And I'm like, I don't know. I found him one. He was listening. One little article, this guy, and I tracked him down. The first EMT to get to Tupac, he's sitting there in Quad Studios. The EMT comes up. He gets out. Tupac is there. He's a bullet lodged in his head between the skin and the skull. It was this close from penetrating his brain, and instead, skin it was embedded in. The guy said he never saw it like that before. Get shot in the hand. And Tupac pulls down his trousers. He's wearing jeans. Trousers, Jeans and his. His boxer briefs. And he sees there's a. There's a. There's a hole in his testicle, but there's no entrance area. Right? There's no. There's no gun power residue, and there's no entrance shot through the jeans or the underwear. And the guy said to me, he had to have shot himself in the balls because he did have the gun here. He used to carry his gun in the waistband. And there was no entrance wound from outside, no entrance mark from outside. So he's like, I've known for years that he shot himself in the. In the Boss. And it was a debate for years and years in hip hop, how did Tupac shoot himself? Who shot Tupac? Blah, blah, blah. And the one was in the Boss.

[Bobby Bones]

Okay, so if he got shot in the head, because I hear hand and then I heard balls, obviously in the head. But if you get shot in the head, they're trying to kill you. If you get shot in the hand and the balls, only they're trying to scare or hurt you. When Tupac was shot, were they trying to kill him?

[Jeff Pearlman]

I honestly don't know. I just don't know. You have to admit, sometimes you don't know. I don't know the intent because I don't know who shot him. Like, I don't know who shot him. So I don't know. My. I think they were trying. Probably trying to rob him and scare him, you know, And Tupac didn't just. You know, he didn't just cower, which you're supposed to do. He never did. So I don't know for sure, though.

[Bobby Bones]

Let's take a quick pause for a message from our sponsor.

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[Tristan Redman]

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[Bobby Bones]

And we're back on the Bobby cast.

All the people that you've interviewed, I'm sure you there's a takeaway with each person. Probably gives you perspective you've never had because, right, you're basically getting as close inside of someone's life as you can get without actually being in their life. What about studying Tupac, like, made you look at life a bit different?

[Jeff Pearlman]

I mean, you asked earlier about being a white writer and I think you, you go into a subject and you think you understand a perspective and then you realize you don't understand a perspective at all. And to me, truly, obviously I've seen poverty. I've never been, I've never lived in poverty, but I've seen poverty. And the different athletes I've written about, I feel like Tupac's sister describing, literally describing the sound of the rats scurrying up and down the baseboard in their Baltimore row house pad, digging into food and eating their food and her saying how haunted she was by that all these years later. I feel like that her describing the level of poverty that they emerged from was deeper and more profound and more painful than my experience writing about people who rise from impoverished situations. And I think it was important for me.

[Bobby Bones]

What are your feelings on Suge Knight after you finished the Book on Tupac.

[Jeff Pearlman]

Terrible. Absolutely. Suge Knight, to me, I put Suge Knight in a trio. If he were starting a doo wop group, it would be him, it'd be Don King, and it'd be Donald Trump. Guys who just take advantage of people. Take, you know, he goes to Clinton to bail Tupac out. I'm gonna bail you out. So I think it was 1.6 million bail. Tupac thinks this is money that Suge is giving him. It's not. It's advanced earnings. And I'll tell you a great, truly great Suge Knight story. The Emblematic two Real quick. Emblematic Suge Knight Stories. Number one, Tupac is filming Gang Related, the movie with Jim Belushi. One day, Suge Knight shows up on set with a car as a gift for Tupac, which he was prone to do. He lavish him with gifts, material possessions, and he shows up and the whole crew is what? They stop filming. And, yo, Pac, this is, it's. I just want to thank you for all you're doing for the Death Row family. This is amazing. Blah, blah, blah, blah. I want to give you this car, bro. This is for you. They hug. Shug leaves. Tupac turns the assistant producer and says, this is mine. Like, what do you mean? I don't own this. I don't own anything. Like, all the cars I have, they're all leased. The place I live least, I don't own anything. My entire life is controlled. Number two, Tupac dies in Las Vegas after the Mike Tyson, Bruce seldom fight. Week later, the family Shug is there in Vegas. He was obviously driving the car. He's there kind of hanging around the family. He promises the family he'll take care of Tupac's ashes. Tupac is cremated. A couple days later, a FedEx delivery guy shows up where Tupac was living. And all the family had congregated in LA with a cardboard FedEx two day delivery box with Tupac's ashes in it. That is how Suge Knight handled the delivery of Tupac's ashes.

[Bobby Bones]

Dang, that doesn't sound like a good dude at all.

[Jeff Pearlman]

Not the best. He did play three games to play three games for the Los Angeles Replacement Rams in 1987, which makes me smile.

[Bobby Bones]

I always think when I hear of people that were just like, like awful people. I always go back to what their origin stories are and what made them, like, what affected their lives in such a tragic way that made them so tragic. And I know you didn't write a book on Suge Knight, but how did Suge Knight become such an awful person.

[Jeff Pearlman]

I dug a lot into Suge Knight. Suge Knight is from Compton. Grew up in a very stable household. You know, his name is Marion Knight. His nickname is Suge because they said he looked like the sugar bear from the. From the cereal box. So went from Sugar bear to sh. Very good household. Played in the marching band, played drums in the marching band, High school football games. He played in the games. Halftime, he'd go and play drums in his football uniform in the marching band, go back and play football. Went to El Camino College for two years. Was a junior college all American as a defensive lineman. Goes to unlv. While he's at unlv, he starts doing work on the Strip as a bodyguard and kind of likes it. Winds up going into the music business working for Dick Griffey for a while. And he works with Bobby Brown as a bodyguard for Bobby Brown. And he just. I think the thing with him, like, I interviewed a lot of guys from Compton who grew up with Suge, and universally, it wasn't that they liked or disliked Suge, but they were like, that guy wasn't a gang banger. This one guy, Mob. James. James McDonald, who grew up in Compton with Suge, is like. He had a quote. I remember exactly. He was like, suge wasn't wearing a bandana. Suge wasn't. Suge wasn't carrying sugar. He was like. He said he was soft as raw, blank of, you know, Val. Like a. You know, he was just. But he want. He was of Compton, but he wasn't of Compton. Like, he wasn't. He wasn't a. He wasn't carrying. He wasn't a blood. He wasn't caring. But he built this image based on size, based on wanting to be a sort of mafioso figure in music, having this image, you know, Death Row. His. His. His line was, you either make a hit or you get hit. And one guy he hired told me he's get hired by Suge. Suge walks him to the window inside Death Row and he says, look out that window. And he goes, all right. He goes. Just so you know, we don't fire guys who don't perform. We throw them out windows. And there's just a million stories of Suge Knight making people kneel naked, drink urine, making people kneel naked, apologize, hitting people, punching people. They kept baseball bats in the closet. Wasn't for a company picnic. He was to beat the crap out of people. He just went from seeing what it was to be tough to deciding, I want to be tough.

[Bobby Bones]

I just wonder where that inferiority complex comes from. Because, again, I look at every villain, even in movies, or even, like, the worst people in real life, and go, there's something that triggered that. And I tr. Because I. For me, I don't believe, unless there's some sort of chemical hormonal thing, that people are just born bad. I think there's trauma, I think. And with Suge Knight, I've always, you know, wondered, like, what about Suge? Because I'd heard the story. I think I've seen a picture of him playing in the high school band in his uniform that I'm like, what made him. Because even the Vanilla Ice story that he tells about Suge not hanging him off the ledge, you know, because it's crazy. I know this is not a Suge Knight interview. I have two questions. The. How did Tupac not have money?

[Jeff Pearlman]

Well, first of all, every. All right. Well, a really telling part of this is he's in prison. And the main woman who took care of him, who's one of the best people I've ever met, is this woman, Yasmine Fula, who is both his business manager, a former Panther, kind of an aunt, godmother, like, figure. And she would visit him every week in prison. And she would always come with family requests, right? Your mom wants a new house. Your cousin needs this. Your other cousin needs this. And it's a classic tale of a guy always coming from nothing and all of a sudden, always giving to everyone. Second of all, he never made that much money. Poetic justice. Janet Jackson made 2 million. I think Tupac may have made a hundred thousand. I remember the exact amount. He was never, you know, Juicy made $17,000. He was never in a huge movie, all eyes on me. Death Row kept a ton of money and then was paying his legal bees legal bills. You know, he had legal fees out the butt, nonstop. So, like, he just never had a great stream of income coming to him, just period and all. Again, all the stuff he, quote, unquote, owned, he actually only owned one car. Every other car he ever had was leased.

[Bobby Bones]

Does his estate have a lot of money now?

[Jeff Pearlman]

I think they're doing pretty well. I mean, the estate wasn't that. They're not bad or anything, but they weren't super friendly with this book, but I'm sure they do. You know, they own a lot of rights. When every time you buy a Tupac shirt in Walmart or Target, you're giving money to the estate. That's not a criticism, that's just A reality. So I think they're doing pretty well.

[Bobby Bones]

That's kind of. Yeah, that's. That's kind of bizarre that after the death, most of the money's made.

[Jeff Pearlman]

I don't like the thing I don't like. Again, it's a judgment. I'm not saying I'm right. I don't love you going to Target and there's like a nine dollar made in some sweatshop in some, you know, poor country shirt with Tupac on it. I just think Tupac, it's a guess. I really think you would have hated that. I don't think you would have liked that.

[Bobby Bones]

My final question is mostly about you. I remember you doing the tick tocks of you talking, but also being like a coffee shop. I don't know which it was, Starbucks or whatever it was. I don't know. But you would have stacks and stacks of papers and you'd have your laptop and. And I just picture like at home. It's like A Beautiful Mind. You've got strings going from articles and like. Because again, that's so much information. How accurate is it that you were just. It was papers everywhere.

[Jeff Pearlman]

I do not have A Beautiful Mind. But it is papers everywhere. It is. I call it my cracked end of paper. It's just like non stop and folders because I print everything out because I'm old enough they still do that. And I like outlining and underlining and this and that. So it's like, where's that?

[Jacob Goldstein]

Where's that thing? Where's that?

[Jeff Pearlman]

It's more Nutty Professor, I think, than Beautiful Mind where shoveled and lost. But yeah, it's kind of. Now all that stuff is in my garage. My wife is like, can we get rid of it? And I'm like, not yet, but soon.

[Bobby Bones]

Okay, last. Last question. And this is this. It could be really stupid, but did you ever want to try crack since you wrote so much about it?

[Jeff Pearlman]

No, I did not.

[Bobby Bones]

Okay, listen, I don't know, I. Maybe you did. I. Oh.

[Jeff Pearlman]

I'll tell you what I wanted to try. There are two things I haven't tried yet. I've only smoked weed a handful of times in my life. I'm just not that guy. And I'm not a big drinker. I still haven't tried Hennessy. I'd like to try Hennessy and I've never smoked a blunt and I like to smoke. But I will tell you, Bobby, and this is cool. My daughter Casey, who's in college for Father's Day last year gave me because There's. There's a line in a Tupac song. I can picture you in heaven with a blunt and a brute from God Bless the Dead. She got me a beer and she couldn't find a blunt, but she got me a joint and gave it for my. For Father's Day last year. Because I used to always say, I can picture you in heaven with a blunt and a brew. So that was kind of a funny gift.

[Bobby Bones]

But no crack. All right, well, hey, I thought you kind of got.

[Jeff Pearlman]

If you want to do it together, I'm in.

[Bobby Bones]

Jeff, I really appreciate the time. And here's the thing. The book Only God Can Judge Me, the Many Lives of Tupac Shakur. If you're hearing this before it's out, because it comes out on the 21st, you can order it. It'll be at your. At your door on the 21st. If you're hearing this after the book is out now. Okay, final, final, final question. Did you become more or less of a fan of the person after writing the book?

[Jeff Pearlman]

More, because it's the same thing with everyone I write about. I love the complexities of people and I love the journeys of people. And actually, it is interesting. The books that are just glowing portraits of people, I don't think they actually make you more of a fan. They just reinforce your fandom. But when you learn about what someone went through, the hardships, the troubles, the highs, the lows, the horrible moments, the great moments, I almost think it has to make you more of a fan because you can appreciate the struggle. So that's where I sit, Jeff.

[Bobby Bones]

Appreciate the time and good luck. I hope you sell tons and tons of books.

[Jeff Pearlman]

Thank you so much. I appreciate it.

[Bobby Bones]

All right, thanks, Jeff. See you later. Man.

[Jeff Pearlman]

Oh, man, thank you so much.

[Bobby Bones]

Hey, who are you doing next? Not. Not for. Not. You know, I'm not going to say anything. Are you working on one already?

[Jeff Pearlman]

I'm doing a book no one's going to buy that's a memoir about my early Nashville journalism career. It's a project, and then I'm either I'm lined up to do the third Laker trilogy book about Kobe Post, Shaq and that whole team, but I don't know if anyone's going to care, so I'm a little torn.

[Bobby Bones]

Well, the. Both books. Both books you just mentioned you went well, nobody's going to care. Nobody's going to care.

[Jeff Pearlman]

I don't know. I'm a self loathing Jew from New York. It's what we do.

[Bobby Bones]

All right, Jeff, good to talk to you, man.

[Jeff Pearlman]

All right, Bobby. I'll see you. Take care.

[Bobby Bones]

Thanks for listening to a Bobbycast production.

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[Tristan Redman]

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[Asma Khalid]

America is changing and so is the world.

[Tristan Redman]

But what's happening in America isn't just the cause of global upheaval. It's also a symptom of disruption that's happening everywhere.

[Asma Khalid]

I'm Asma Khalid in Washington, D.C. i'm.

[Tristan Redman]

Tristan Redman in London, and this is the Global Story.

[Asma Khalid]

Every weekday we'll bring you a story from this intersection where the world and America meet.

[Tristan Redman]

Listen on BBC.com or wherever you get your podcasts.

[Jacob Goldstein]

This is Jacob Goldstein from what's yous Problem? Business software is expensive. And when you buy software from lots of different companies, it's not only expensive, it gets confusing. Slow to use, hard to integrate. Odoo solves that because all Odoo software is connected on a single affordable platform. Save money without missing out on the features you need. Odoo has no hidden costs and no limit on features or data. Odoo has over 60 apps available for any needs your business might have, all at no additional charge. Everything from websites to sales to inventory to accounting. All linked and talking to each other. Check out Odoo at o d o o dot com. That's o d o o com.

[Tristan Redman]

This is an iHeart podcast.