The Ballad of Biggie and Tupac

Summary

Podcast Summary: Stuff You Should Know

Episode: The Ballad of Biggie and Tupac
Date: January 22, 2026
Hosts: Josh and Chuck
Podcast: iHeartPodcasts

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Overview

In this in-depth episode, Josh and Chuck delve into one of music and pop culture’s most infamous rivalries—the story of Tupac Shakur and The Notorious B.I.G. (Biggie Smalls). They trace the roots and trajectory of their friendship, its tragic deterioration into the bloody East Coast vs. West Coast hip-hop feud, and the circumstances that led to the deaths of both men. The episode is candid about the real violence, complicated loyalties, intense media focus, and the myths that continue to surround their legacies.

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Key Discussion Points and Insights

Setting the Stage: 90s Hip-Hop and the Need to “Be Real”

• The rivalry between Tupac and Biggie was pivotal in defining and popularizing the East Coast vs. West Coast era in 90s rap.
• Both rappers felt pressured by the industry, fans, and media to embody the hard-edged lifestyles they rapped about, at risk of being branded “fake” or “studio gangsters.”
  • "A lot of people make a case that lifestyle was essentially demanded by fans and the media..." (02:14, Josh)

Tupac’s Origins and Rise

• Born Lesane Crooks in Harlem, 1971; mother Afeni Shakur was a prominent Black Panther, famous for her acquittal in a high-profile bombing case.
  • "He was actually renamed by his mom when he was about a year old after indigenous South American revolutionary Tupac Amaru II..." (04:26, Chuck)
• Early life marred by poverty, mother’s addiction, and self-reliance—selling drugs as a teen in Marin County near San Francisco.
• Excelled in English and poetry; mentored by his English teacher, Leila Steinberg, who became his first manager and supporter.
• Early break as a dancer (and later rapper) in Digital Underground; stood out for his serious, hard-hitting lyrical style.

Biggie’s Background and Breakthrough

• Born Christopher Wallace, 1972, Brooklyn; raised by a Jamaican immigrant mother committed to education.
• Attended the esteemed George Westinghouse high school with DMX, Busta Rhymes, and Jay-Z.
• Also began selling drugs in his youth due to family’s financial struggles; spent nine months in jail in the early 90s.
• Demo tape landed him on Source Magazine’s “Unsigned Hype,” catching the attention of Sean “Puff Daddy” Combs.
• Signed to Bad Boy Records; performed under Notorious B.I.G. due to legal reasons.

Friendship Turns to Rivalry

• Tupac mentored Biggie at first; the two were close, with Biggie staying at Tupac’s LA home.
  • "...whenever Biggie went out to LA, he stayed on Tupac's couch." (16:15, Josh)
• Sean Combs was reportedly jealous of their friendship and disliked by Tupac, whom he saw as an executive “playing” gangster.
• Tension escalated with the infamous 1994 Quad Studios shooting in NYC, where Tupac was shot and, seeing Biggie and Combs upstairs, concluded they were involved—though there’s no evidence of this.
  • "Biggie was like, I have no idea what he's talking about. And Tupac just decided that if Biggie Smalls hadn't set him up, he had at least turned his head and let all of this happen." (24:28, Josh)

The East Coast vs. West Coast Divide

• Quad Studios shooting crystallized the beef, aligning Tupac and Biggie with the Bloods and Crips, respectively, making peaceful reconciliation nearly impossible.
• The rivalry was fanned by media coverage—especially the September 1995 Vibe magazine cover—and by figures like Suge Knight (Death Row) and Sean Combs (Bad Boy).
• Suge Knight’s infamous call-out at the 1995 Source Awards (“Any artist who don’t want to worry about the executive producer... come to Death Row!”) openly escalated tensions.

Paranoia, Betrayals, and Violent Escalation

• Tupac’s time in prison (for sexual assault) deepened his paranoia and conviction that Biggie and Combs had orchestrated the shooting. Biggie’s release of “Who Shot Ya?” was perceived by Tupac as a direct taunt, though it predated the attack.
  • "It seems like it was a one-sided beef, but the beef on Tupac's side was so energetic that you couldn't just ignore it." (24:28, Josh)
• Personal betrayals included Tupac hiring Biggie’s wife, Faith Evans, for a song, later (apparently falsely) claiming he slept with her.
• March 1996 Soul Train Awards: both entourages faced off with guns drawn—miraculously, without actual violence.

Murders of Tupac and Biggie

• Tupac's Death (September 1996, Las Vegas): After a Tyson fight and altercation with Orlando Anderson (a Crip), Tupac was shot—Anderson and fellow Crips believed responsible.
  • “A few hours later, Suge Knight and Tupac are at a stoplight. Cadillac pulls up next to them, and the car is shot up and Tupac is dead six days later at 25.” (42:36, Chuck)
• Official suspicion initially landed on Combs and Biggie, but evidence pointed to Crips’ retaliation. 2019 memoirs and a 2023 arrest (Keefe D) furthered that narrative, with a trial pending for 2026.
• Biggie's Death (March 1997, LA): Killed in a similar drive-by after a Vibe party. Theories implicated Suge Knight, Combs, even the LAPD—no one ever charged.
  • “...it certainly seems to have been a contract hit...was almost certainly a conspiracy.” (46:10, Josh)

Legacy and the End of the Feud

• Both released posthumously: Biggie’s Life After Death (sold over 10 million), Tupac had nine posthumous albums.
• The once-explosive East vs. West rivalry faded as the hip-hop scene decentralized—hosts credit Outkast and the rise of Southern hip-hop for “ending” the beef.
  • "You can thank Outkast for ending the east coast, west coast rivalry." (48:24, Josh)

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Notable Quotes & Memorable Moments

• Chuck: "To me, they're sort of victims of that whole thing in a lot of ways." (03:06)
• Josh, on the pressure to be “real”: “It was inevitable that it would end in death and violence.” (02:45)
• Chuck, on Tupac's early years: "He studied poetry. He continued to after he dropped out. And actually, his teacher, his English teacher, ... ended up becoming his first manager." (05:42)
• Josh, on Biggie’s rise: "He excelled in English in high school, but also like Tupac, his family was not exactly well to do ... so he started selling drugs on the side." (11:31)
• Chuck, summarizing Biggie’s school: "George Westinghouse Career and Tech Education High School, which had quite an alumni base as far as hip hop goes, because DMX, Busta Rhymes, love Busta and Jay Z all went there." (10:24)
• Josh, on the role of the labels: "You had Bad Boy with Sean Combs, Death Row Records on the other side ... and one of those guys was ... Marion Suge Knight. He was a blood." (28:50)
• Chuck, on the Suge Knight Source Awards moment: "He invited any ... rapper who didn’t want to worry about the executive producer trying to be in all the videos ... come on over to Death Row Records." (29:58)
• Josh, on Tupac's declining trust: “There's pretty widespread acknowledgment or belief that he was suffering from substantial mental health issues while he was alive, and that that had a huge impact on the way that he interacted with people.” (27:40)
• Josh, on the legacy: "Biggie Smalls and Tupac usually kind of battle for first or second place on most lists of the greatest rapper of all time. My money’s on Biggie Smalls." (32:57)

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Important Timestamps & Segments

• [03:47]–[08:50]: Tupac's upbringing, family, and early career
• [09:38]–[13:38]: Biggie’s background and path to hip hop
• [15:10]–[17:50]: Tupac and Biggie’s early friendship
• [20:44]–[24:28]: Legal troubles, shootings, and beginnings of the feud
• [29:58]–[31:29]: The Source Awards, Suge Knight’s provocation
• [36:13]–[41:33]: Further escalations—Soul Train Awards, Faith Evans, media involvement
• [42:36]–[44:24]: Tupac's murder—details and aftermath
• [45:36]–[47:41]: Biggie’s murder and conspiracy theories
• [48:04]–[48:34]: The rivalry's demise and the rise of Southern hip-hop

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Final Reflection

Josh and Chuck present not only the chronology but also the context of two extraordinary talents whose lives and deaths reflected both the intensity and the tragedy of their times. They balance anecdote, history, and their own fandom with candor and humor—making the saga feel immediate and real, while never losing sight of the deep sorrow at its core.

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For listeners wanting a captivating, thorough walk-through of the Biggie vs. Tupac saga—complete with context and personality—this episode hits every note.

(Note: Timestamps may vary by a few seconds due to transcript formatting.)

Transcript

[A]

This is an iHeart podcast. Guaranteed Human. Welcome to Stuff youf Should Know, a production of iHeartradio.

[B]

Hey, and welcome to the podcast. I'm Josh and there's Chuck and Jerry's here too. So this is a good old fashioned stuff you should know. One of our ongoing hip hop editions. Yeah, I feel like a dork anytime I say hip hop, so I usually say rap.

[C]

Yeah.

[B]

But regardless, that's what we're talking about.

[C]

Yeah, we're talking about Biggie and Tupac and we want to issue a warning and a trigger warning, no pun intended there. But this one's obviously gonna. Because we're talking about the lies of these two guys who were in many ways real gangstas. A lot of stuff went down, including sexual assault and gunplay and murder. And it's, you know, it's probably not appropriate for the younger listeners. And so we just wanted to get that out there. Hopefully if you know anything about Biggie and Tupac, you know that there's some more adult content coming your way.

[B]

Nice coa man.

[C]

Yeah.

[B]

So, yeah, we are talking about Biggie and Tupac and they are pretty well known. If you listen to either one of them or even kind of have a passing awareness of hip hop, especially in the 90s, you probably know that Biggie and Tupac had probably the biggest rivalry in the hip hop world. It's referred to as a beef between one another. So much so that it actually triggered or caused, at the very least popularized the East coast versus West coast thing of rap in the 1990s. That was huge. It was the central focus of rap during basically that whole decade.

[C]

Yeah. And sadly would leave both of them dead from violence. It was. I hope that's not a spoiler for anyone, but yeah, at very young ages. It's super sad what happened to those guys and just super sad that that was brought about because of just sort of the lifestyle that went along with their careers, you know?

[B]

Yeah. And a lot of people make a case that lifestyle was essentially demanded by fans and the media and certainly fostered and nurtured by fans in the media. And so I think both Biggie and Tupac and all the people around them and other rappers basically felt like they had to act like they. The stuff that they rapped about or else they would be fake baby gangsters sometimes or studio gangsters even worse.

[C]

Well, yeah, yeah.

[B]

And then they were also surrounded by literal Bloods and Crips. So it essentially had. It was inevitable that it would end in death and violence.

[C]

Yeah. I mean, I think Hip Hop more than other types of music, too. There's an expectation to be. To be real again. God, all these puns flying out of my mouth.

[B]

Oh, from Sabre's Hill.

[C]

Yeah, of course. But to be real, and like you said, if you were found out, to be sort of rapping about something and really kind of fake in real life, like, that's no good for your career as a hip hop artist. So it's sort of, you know, I don't know. To me, they're sort of victims of that whole thing in a lot of ways.

[B]

Yeah. But at the same time, they definitely bought into it. Oh, yeah. I mean, they essentially laid the groundwork for that. It's just. It's crazy because it's just such a ubiquitous, widespread thing for so long. It's strange to. To think that you can trace it back to one group, one duo, essentially.

[C]

Yeah. So we're going to tell you a little bit about Tupac and his beginnings, a little bit about Biggie, and then once they met up, kind of what happened from there. But as far as Tupac goes, he was born in 1971, same year as me. He was born in Harlem. His mother was Afeni Shakur, and she was one of the Panther 21. I'm pretty sure we talked about them in the Black Panther episode, but they were part of the Black Panther party, the ones who were accused of carrying out a bombing campaign. She did win an acquittal in court defending herself, and exposed a lot of stuff about undercover cops and the tactics they used that were very untoward. But Tupac was born about a month after that trial and born Lesane Crooks. But it's not like he changed his name to be a cool hip hop guy later. He was actually renamed by his mom when he was about a year old after indigenous South American revolutionary Tupac Amaru ii. So he's essentially was always Tupac.

[B]

Yeah. He was Named after an 18th century Incan, I believe, who led a rebellion against the Spanish. Little known fact. I didn't know that, did you?

[C]

I did not.

[B]

So I usually think I associate Tupac with New York because pretty much all the movies he was ever in were all set in New York. But he's from San Francisco. I mean, he was born in Harlem, but his family moved to San Francisco, or actually Marin county, which is a suburb of San Francisco, pretty early on in his life. And at the time, his mom was struggling with a crack addiction. So Tupac was essentially on his own from a very young age. And as black kids at the time in the 80s in particular, did to make money when you were in a situation like that. He sold drugs. And that's how he supported himself for a long time, while he was even going through school, too.

[C]

Yeah. And he was like, we'll see. Biggie was. He was a really good English student, and I bet a lot of hip hop performers were good in English. You know, it just sort of makes sense. But he dropped out of high school. He studied poetry. He continued to after he dropped out. And actually, his teacher, his English teacher, one of them, Leila Steinberg, was like, hey, I see a lot of potential in you. You can crash on my couch when you need to. And she ended up becoming his first manager.

[B]

Yeah. And she said, you always have to wear that. That bandana around your head just so like you do. Because I love it.

[C]

It looks super cool.

[B]

I know we've also talked about this before, but he was a member of Digital Underground with Humpty Humphrey of the famous Humpty Dance. He's shown dancing in the Humpty Dance video in the background. He was a dancer for Digital Underground, but later, I think rapped on some of their albums.

[C]

Yeah.

[B]

But even from the outset, his whole vibe was much, much edgier than Humpty Humps was like, Humpty Hump was rapping about how big his nose was and having sex in Burger King bathrooms. Right. Like, Tupac was rapping about what part poverty and crime are like in the black community.

[C]

You know, he. He. He didn't go by Humpty Hump.

[B]

What was his. What did he go by?

[C]

That was Shock G. I've heard him.

[B]

Referred to on other songs as well.

[C]

All right. AKA Humpty Hump. So.

[B]

Okay.

[C]

Yeah, you weren't completely wrong.

[B]

A little. Little side. I would direct people to the Merge song Risky Business that features Humpty or. Or Shock G. It's a pretty cute little song.

[C]

All right.

[B]

So Tupac goes out on his own. He's got, like I said, a totally different vibe. And he released a solo album called tupacalypse. Now, there was no other title that it could have possibly been than that.

[C]

Yeah, for sure.

[B]

But the problem was, like, he was keeping it real. So there was nothing in the studio that he was producing that could be played on the radio.

[C]

Yeah.

[B]

So it was an underground sensation, but publicly, most people had not heard of Tupac at that point.

[C]

Yeah, for sure. He. Dan Quayle kind of gave him a little more press when he blamed that record Tupacalypse. Now, on the shooting of a Texas State Trooper. So he was in the news a little bit, at least. And he started acting kind of right afterward. In 1992 and 1993. He put out or he was in the movies. Juice and Poetic justice, both really great movies. Juice is awesome, actually. So is Poetic Justice. I love both of those movies.

[B]

The one I've seen him in, I think I saw Juice. I didn't see Poetic Justice. I saw above the Rim. He was really good in above the Rim.

[C]

I never saw that one.

[B]

Oh, that's a good one. You should see it.

[C]

All right, we need to get together and have a Tupac watch party, I guess.

[B]

Okay, let's do that. Yeah.

[C]

But he started getting a little more famous sort of slowly. And this is when, kind of the early 90s, at the very beginning of his career, is when he first started getting into trouble and getting like a real reputation as sort of living that lifestyle.

[B]

Yeah, I mean, like for real. He was involved in a shootout, a shootout at the Marin County Festival where he lived, where he had just performed that killed a six year old who was playing on a school ground nearby. Yeah, he shot at off duty police in Atlanta in 1993 when he tried to prevent them from beating up a black motorist. And those charges were thrown out because it turns out the cops are off duty, didn't announce themselves as cops and were super drunk. But you know, those kind of things, like his legend as like a thug living the thug life, which I think he basically coined, that just formed and melded really quickly right out of the gate. Like this guy was legit as far as his. His fans were concerned.

[C]

Yeah, for sure. So that's Tupac's early days. Biggie Smalls was born. He's a little younger. He was born in 1972 in Brooklyn. His name was Christopher Wallace. He was born to Jamaican immigrant parents and his mom was a preschool teacher. His dad was a politician in Jamaica, but ended up leaving when he was 2 years old and became a welder in the United States. But his mom, Valletta, really thought a lot about education, obviously, as a teacher. So she took on a second job just so she could send him to a very well regarded high school, and then later went to George Westinghouse Career and Tech Education High School, which had quite an alumni base as far as hip hop goes, because dmx, Busta Rhymes, love Busta and Jay Z all went there.

[B]

Yeah, I'm guessing I didn't. I wasn't able to find it, but I'm guessing they crossed paths, may have been there at the same time.

[C]

Yeah. I mean, Donald Glover would have gone to my high school had they not sent him to the School of the Arts.

[B]

Oh yeah.

[C]

And I saw him in New York City a few feet from me when I was there in December. And let me tell you, dude, I don't know if I've ever seen a more handsome grown man in person. With my eyeballs, really. He's astoundingly good looking. And I wanted to go over and say like, hey man, we grew up in the same neighborhood basically, and you're.

[B]

Really good looking, you're really handsome.

[C]

But he, I'm such a big fan of his, but from his music to his acting. But he was with his family and like, it's just like, I'm just not going to do that.

[B]

Instead you got in your car and shouted Redan High rules and like laid rubber peeling out of the parking lot.

[C]

Yeah, that's right. Sure. Danger Mouse went to my high school too, though.

[B]

Oh yeah. Oh, I forgot about Danger Mouse. Danger Mouse did that Gray album with the Beatles and Jay Z, right?

[C]

I don't know.

[B]

We'll find out the hard way. So like you said, a lot of hip hop artists are probably, or probably were, are good English students. And Biggie Smalls was not an exception to that. Like Tupac, he was actually. He excelled in English in high school, but also like Tupac, his family was not exactly well to do. Remember his mom took a second job to put him just through high school. So he started selling drugs on the side, crack again, this is the 80s, and eventually dropped out of high school. And I think any kind of straight and narrow he might have been on from high school was just kind of removed. And he started to get in like actual trouble with the cops.

[C]

Yeah, he ended up in jail. Actually. He spent nine months in jail at one point because he couldn't make bail. And once he got out, he made a demo tape under the name Biggie Smalls. His nickname as a kid was Big, but I think that came from a gangster in a movie from 1975 called let's do it Again. Biggie Smalls did. And he said that he wasn't trying to get into a career, he just sort of did it for fun. And that got him on Source Magazine's list in 1992 of unsigned and their Unsigned Hype column, which eventually put him on a compilation with other unsigned rappers, which eventually landed him on the ears of a 23 year old named Sean Combs.

[B]

So, yeah, Sean Combs, Puff Daddy Diddy. People have probably heard of him by now for all sorts of reasons. His career as a 23 year old was as vice president of Uptown Records. And pulled being a entrepreneur and all sorts of other things, he decided to found his own record company, Bad Boy Worldwide Music Group, usually known as Bad Boy Records. And one of the first things he did was sign Biggie Smalls. And they became paired up in the media. They hung out, they were friends, they were fairly close. But like those two were inseparable as far as like the public was concerned. Whether that was fully true or not.

[C]

Yeah. And his, when he put out his first single, it was under the name Notorious B.I.G. because of legal issues, I guess, with the movie Biggie Smalls. Was that it?

[B]

That's my take, yeah.

[C]

Okay, so he was Notorious B.I.G. iG officially everyone called him Biggie. Of course he had a kid in 93 with his high school girlfriend, Jan Jackson, not Janet Jackson. And he hadn't really broken through at this point even though he was with Sean Combs at the time. But he, you know, so he continued to kind of deal drugs. Apparently Combs was like, he can't do that kind of stuff if you want to get anywhere. But he broke up with his high school sweetheart who he had his first kid with. And a few months after that ended up with Faith Evans who was also on the Bad Boy label. And that is Biggie and his start. So good. Time for a break.

[B]

Yeah, we're at 1993. Tupac's already a star and Biggie's starting to come up.

[C]

All right, we'll be right back. S Y L Y S K SK.

[B]

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[C]

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[B]

Yeah. So it's no wonder millions of business owners rely on Spectrum business to keep them connected. Visit spectrum.combusiness to learn more. Restrictions apply. Service is not available in all areas. So one of the things you may or may not know, if you're just kind of passingly familiar with the beef between Biggie and Tupac is that they started out as friends. They were actually pretty good friends for a while. Tupac, like I said before we broke, was already a star. His star was established and still growing. Biggie was just starting to come up. He was pretty, pretty well known around New York and Tupac kind of became a mentor to him. They met in 1993 and they hung out with a bunch of other people, played around with a bunch of guns at Tupac's house. And they became close enough that whenever Biggie went out to la, he stayed on Tupac's couch.

[C]

That's right. Like I said, he kind of considered Biggie like one of his lieutenants at the time and definitely was a mentor. Biggie's debut came out. It was called Ready to die in 1994. And before that, Biggie was like, you know what? I think you should just be my manager and take over from. Take over for Sean Combs. And Tupac was like, nah, man, you need to stick with that guy. Apparently Tupac wasn't a big fan of Combs, but, you know, he said that I had a feeling he just didn't want to get into managing him.

[B]

Well, he said, he'll make you a star. And I think he did know that, like, you know, Tupac wasn't a manager or a label owner. Like, he was a performer. And Sean Combs liked to think of himself as a performer, but really he was an executive. So it probably was the smarter move to stay with him, at least at first. Right?

[C]

Yeah.

[B]

The problem was, is Sean Combs, again, remember, inextricably linked BFF with Biggie, as far as the public's concerned, was actually jealous of Biggie and Tupac's friendship. He wanted to be friends with Tupac. He was jealous that Biggie got to be friends with Tupac. The reason Tupac didn't care about being friends with Sean Combs is that he thought Sean Combs was basically a poser. He was a record executive playing like he was a hardcore rapper and he didn't have much respect for him. And I think that that really kind of came through to Sean Combs after a little while. And he didn't. He started not liking Tupac.

[C]

Yeah, that's right. So the beef is sort of the beef seed is planted as they are. You know that old saying, where's the beef seed?

[B]

It's been planted. Exactly.

[C]

Ready to die, like I mentioned, was Biggie's debut in 94. It was a big hit. It went double platinum about a year later, which means a lot of records were sold. And this was when the west coast was sort of the. Like, all the big hip hop stars were mainly out of the West Coast. So he was kind of the biggest thing coming out of New York right off the bat. And it's a great record. He was, you know, he. He rapped A lot about, you know, sort of like the lifestyle and the gangsta stuff that he was doing. But also there was a lot of vulnerability on that first record, too.

[B]

Yeah, yeah. He and Tupac wasn't shy about rapping, about mental health and stuff like that. And up to this point, like, you did not talk about that kind of stuff. It was all about partying and having sex and, like, doing drugs and all that stuff. You didn't talk about being paranoid or, like, super worried about being killed or anything like that. And I just. To kind of set the scene. Can we talk a little bit about the brief history of hip hop up to that. That point and how big of a deal it was when Ready to Die came out?

[C]

Sure.

[B]

Because you said that the west coast had kind of taken over from the east coast, like from Slick Rick and LL Cool J and all them, the ones who were coming up in the 80s. At the time that Biggie Smalls record came out, everyone was all about Dr. Dre, Ice Cube, Snoop Dogg, all these guys. Like, that's where rap was. It was on the West Coast. So for somebody to. To come along and basically snatch that away and bring it back to New York, it was just a really big deal. And. And it took a rapper of the caliber of Biggie Smalls to do something like that because there are tons of other albums that had come out. Like Tribe Called Quest had three albums by this time. And yet the Biggie Smalls record coming out just completely undid, essentially caused an earthquake in the rap world and tilted everything back to New York.

[C]

Yeah, for sure. So as this is happening and Biggie's blowing up in a big way. Tupac is in New York filming a movie in 1993, and we get a new guy on the scene, or he was actually on the scene, but a new guy, as far as his podcast goes, named Haitian Jack. And he starts hanging out with Tupac. Tupac likes this guy. They start partying together. Biggie knows about Haitian Jack because he was pretty familiar with the street gangs of New York. And he warns his friend Tupac, and he's like, man, this guy is real trouble. So, like, you gotta watch out. You should probably stay away from this guy. Cause, like, he's a super violent dude. Like, I know we're all real, but this guy is. He will land you in jail probably at some point. So stay away or get you killed. Yeah.

[B]

So things are going along. Biggie and Tupac are friends. One's in New York, one's on the West Coast. It turned out Biggie was pretty right in warning Tupac against Haitian Jack because shortly after that, Tupac met a girl named Ayanna Jackson. She was 19 at the time, while he was in New York filming, hanging out with Haitian Jack. And she alleged that Tupac, Haitian Jack, the road manager for Tupac, Charles, Man Man Fuller and another man, I couldn't find who he was, gang raped her, and she called the police. Afterward, the police showed up, they found guns in the room.

[C]

And.

[B]

And now Tupac is in big, big trouble again. Right. So two threads begin here. One is Tupac is now charged with sexual abuse, sodomy, and possession of guns. Illegal guns. Yeah, that starts. That thread starts. It will pick up again later. But another thread starts, which is a dispute, a beef now with Haitian Jack because he thought that Haitian Jack had dropped the dime on Tupac to get out of the trouble for this gang rape charge. Yeah.

[C]

So Haitian Jack had his case separated from Man Man Fuller. And Tupac, he pleaded down to a lesser charge. He pleaded guilty to two misdemeanors and avoided jail time. Tupac always said he was innocent and that he was set up and sold out by Haitian Jack. But that, you know, we need to point out, that completely contradicts the story of the victim from Ayanna Jackson. So. But, you know, the whole point of this is there's, like you said, there's now this official beef that kind of, again, planted the seed of what would happen to he and eventually Biggie moving forward.

[B]

Yeah, and the thing that really kind of blew this, this whole thing up is Tupac said as much. He said Haitian Jack cooperated with the police. This major actual gangster in New York cooperated with the police in an interview with the New York Daily News. So the New York Daily News prints Tupac saying that. And that did not make Haitian Jack very happy. Those two separated immediately. They didn't talk anymore. They weren't friends anymore. They didn't hang out. And now Tupac had essentially an enemy in Haitian Jack, which is, from what I can tell, not what you wanted.

[C]

No, not at all. So the case is moving forward. At this point, Tupac is financially strapped because while he is making money, he's spending it faster than he's making it. He's also helping out friends and family with their finances. So there was an invitation from a guy named Jimmy Henchman Roseman. He knew Sean Combs, he knew Haitian Jack, and he said, hey, Tupac, why don't you do a guest spot for this rapper, Little Sean? He's in Biggie Circle, he's a guy with Sean Combs as well. We'll pay seven grand. He needed the money, so he did it. He shows up at Times Square at Quad recording studios on November 30th along with three of his guys. And before getting on the elevator to go up and record, they were met by these other three guys who draw guns, tell him to get down on the ground. Tupac draws his gun and he ends up being shot. He ends up being robbed. He ends up being beaten pretty badly. And Combs and Biggie and Jimmy Henchman Roseman were up in the studio at the time they were there. So all of a sudden Tupac is getting wheeled out on a gurney, sees those guys and he flips a bird at Biggie and his crew. Cause he thought they were in on this attack. And that's when the beef really started between these two.

[B]

Yeah. And Biggie was like, I have no idea what he's talking about. And Tupac just decided that if, if Biggie Smalls hadn't set him up, he had at least turned his head and let all of this happen. Like he knew that it was going to happen. He didn't warn him. There's no evidence whatsoever either one of those things happened. And Biggie Smalls always is like, no, like this had nothing to do with it. After Tupac died, he was obviously heartbroken and spoke in public about how sad he was that Tupac was dead. It seems like it was a one sided beef, but the beef on Tupac side was so energetic that you couldn't just ignore it. There was just a divide. And the divide was so great that Bloods hung out with one side. I think Tupac side and Crips hung out with Biggie's side.

[C]

Yeah.

[B]

And you have that kind of thing. Like there's very little chance of like reconciling or accidentally hanging out because you ran into each other on the street and you kind of patch things up. That is not going to happen with you now hanging around with the Crips and the Bloods.

[C]

Yeah. And no one ever really got to the bottom of who was behind that shooting. There's a lot of disagreement and people pointing fingers and claiming this and that. I guess we don't need to totally get into that. But after he was beaten and shot and robbed, he's bandaged up, he's in a wheelchair, he's still got this court case going on. And he is found guilty of sexual assault. He's acquitted on the other charges, and he's sentenced to 18 months in prison. Where his third album came out. Me against the World came out while he was in prison serving that sentence.

[B]

Dude, if you want cred, release your rap album while you're in prison.

[C]

Yeah. Called Me against the World.

[B]

Yeah, exactly.

[C]

Yeah.

[B]

So while Tupac was in jail, I don't remember how long he was in for.

[C]

18 months.

[B]

18 months. Okay. While he was in jail, Biggie releases a track called who Shot you? And Tupac interprets that as it was completely directed to him. It was essentially Biggie Smalls gloating about having set up Tupac. And now Tupac was in jail and he'd been shot. And that seems to not be the case at all. Biggie Smalls apparently wrote that song before the Quad City shooting. And again, just from all evidence, it seems like Biggie had no problem with Tupac. This is all in Tupac's head. Like this whole east coast, west, west coast beef seems to have come from Tupac being paranoid, essentially. And I looked up why he might have been paranoid. And apparently there's pretty widespread acknowledgment or belief that he was suffering from substantial mental health issues while he was alive and that that had a huge impact on the way that he interacted with people. The level of trust he would afford even the closest people. Like, I think it was very easy to fall out of his favor because you might do or say something that he suddenly found suspicious and now all of a sudden, like you were his enemy. Like you would do something like set him up or rob him or pay for him to be killed or something.

[C]

Yeah, I wondered about that. I'm glad you looked into that.

[B]

Thank you. I am too.

[C]

You're welcome. Maybe we should take another break.

[B]

Yeah.

[C]

All right, we'll take another break and we'll get back to it right after this.

[B]

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[C]

All right, so I don't need to go over what we've been talking about because everyone's listening. So at this point, the record labels that were handling this kind of music, it wasn't like the major label stuff at this Time like that would happen in the future. But it was basically hip hop labels. You had Bad boy with Sean Combs, Death Row Records on the other side. That company was founded about the Same Time in 1992 by Dr. Dre and a few other guys. And one of those guys was his former bodyguard, Marion Suge Knight, spelled S U, G E. He was the CEO of Death Row Records.

[B]

Yeah.

[C]

And he was a blood. Like, he was, you know, he was a straight up blood from South Central Los Angeles.

[B]

Yeah. So. And he's now the CEO of Death Row Records. Right. So that automatically makes Death Row Records like another. It's this legit music label. As far as, like, the stuff that the artists on the label are rapping about. The CEO of the record label is a blood, not a form of blood. A blood.

[C]

Yeah.

[B]

So we talked about how the Quad Studio shooting, like, really kind of started the beef. The thing that made that beef really genuinely public came at the awards show for Source magazine. Their annual awards this time. This One was in 1995, where Suge Knight, who'd been visiting Tupac in jail and apparently had bought into Tupac's theory that Sean Combs and Biggie Smalls had set him up to be shot and robbed. Suge Knight was accepting an award, and during his speech, he invited any. Any rapper who didn't want to worry about the executive producer trying to be in all the videos, which was a direct shot at Sean Combs. Yeah. He said, come on over to Death Row Records. And I mean, if you go back and look at, like, Biggie Smalls videos and, like, basically any rapper on this label at the time. Oh, yeah, Sean Combs is probably going to pop up making a cameo, if not dance on it. And usually with his shirt wide open. Yeah. He really was not. He was not what they, like, Death Row Records was doing. And so, like, Suge Knight made a pretty good point. Like, if you were really actually looking for legit stuff, come over here. But saying it publicly and doing it by taking a shot at Sean Combs at the Source Awards.

[C]

Yeah.

[B]

While you're accepting an award, it was a big deal that was. That really kind of made that beef public, and it turned into east coast versus west coast essentially immediately.

[C]

Yeah. I mean, I remember at the time thinking. Because I remember just seeing. And it wasn't just rappers, like, they had, like, some R and B acts, and I feel like. I feel like Combs was always in those videos, just like. Like you said, either dancing or just like. Yeah, yeah. In the background.

[B]

Yeah.

[C]

And I remember thinking about the time, at the time, and this wasn't like, my hip hop was all, like, earlier stuff and Tribe Called Quest and that kind of thing. And, you know, Dr. Dre and Snoop. I was into that at first, but this generally wasn't my thing. But I remember thinking like, this guy's like, he sucks. Like, he's not. He's not a talented artist. No, because he wasn't, I guess, you know, he was a. Like you said, an executive and a producer. And I was. I remember thinking that, like, why is he always throwing himself in there in front of the camera? Like, he sucks.

[B]

Yeah. And he was dorky even compared to who were essentially mainstream rap artists like Tupac and Biggie Smalls.

[C]

Oh, yeah.

[B]

No shade on them. But there were way more underground rappers at the time putting out really good stuff. Tribe Called Quest is a really good example of that. That when you compared them to them, he became even. Even more cringy. Right?

[C]

Yeah, yeah, for sure.

[B]

He was. It was. And he definitely, like, kind of brought down the credibility of. Of the label and all the artists on it. For sure. Like, Biggie Smalls was exponentially too good for Sean Combs. Sean Combs just kind of had him under his thumb.

[C]

Yeah, absolutely.

[B]

Which is sad because, I mean, Biggie Smalls is. Biggie Smalls and Tupac usually kind of battle for first or second place on most lists of the greatest rapper of all time. My money's on Biggie Smalls.

[C]

What about you as the greatest rapper of all time?

[B]

Well, it's between Tupac and Biggie. How about that?

[C]

Oh, okay. Cause Chuck D, like, dead in the bullseye for me.

[B]

Oh, yeah.

[C]

Oh, yeah. I was always a Public Enemy guy. Like, that started in high school.

[B]

I like them, too, but I don't know. I think. I don't like the. I don't like the instrumental track to a lot of their stuff. It's too hard and brawl edgy for me.

[C]

Yeah, I liked it. I mean, trust me, I was way more into, like, the Tribe Called Quest and Farside and Jungle Brothers and like, that kind of style. So. Public Enemy. Me being into Public Enemy in high school is definitely kind of a weird thing.

[B]

Yeah.

[C]

But as I was listening to the Smiths and the Cure.

[B]

That's right. No, I'm with you. I was listening to the Smiths and the Cure, but also like boot camp. Click. Like Smith and Wesson, Nas, Wu Tang, Gangstar.

[C]

Yeah, see, I never. I like Gangstar, but I never got into Wu Tang.

[B]

They were pretty good. They were they were better solo. I think most of, like, Method man and RZA were better solo than Wu Tang together, but whatever.

[C]

And this is two middle aged white guys discuss their hip hop past.

[B]

I do. I do have to say that Dr. Dre's the chronic was literally life changing.

[C]

Oh, for sure.

[B]

And it's not just me that that happened to. I think that changed a lot of people's trajectory.

[C]

I was one of them, man. I know that thing by heart inside and out. Yep, it's a fun listen. When I put it on, a lot of nostalgia floods back.

[B]

It is. I thought the same thing would be for Doggy Style, Snoop's debut solo album. It's not. It does not hold up.

[C]

Yeah, I mean, it's not. It wasn't as good as the Chronic.

[B]

By a mile, but I liked it as much as the Chronic at the time, and I don't anymore.

[C]

Yeah, I'm with you. And part of that may have to do with the fact that Snoop Dogg has, I don't know, become the Snoop Dogg of today.

[B]

Man, he's amazing. He's now the owner of Death Row Records.

[C]

No, he's awesome. But I just feel like he's a bit overexposed for my taste.

[B]

Oh, I see. He's like the.

[C]

The Peyton Manning of the hip hop world.

[B]

He's the Pedro Pascal of rap.

[C]

Okay. Even better said.

[B]

But he's an American treasure, though. I mean, like, he was an Olympic mascot. Along with flavor. Flavor.

[C]

Now I'm picturing Snoop Dogg, Pedro Pascal, and Peyton Manning and just sitting at lunch just saying, like, guys, isn't this great?

[B]

I could see that. Talking about mutual funds.

[C]

Yeah. We should do something together because we're not out there enough.

[B]

Right. It'll blow everyone's mind.

[C]

All right, so we are in September 1995. At this point. Suge Knight has dropped the bomb at the Source Awards, which I'm sure did not sit well with Sean Combs. And Tupac is in prison at this point. And Knight and Combs go to the same party here in Atlanta at what was called the Platinum House. It's a strip bar over on Piedmont Road near the Colonnade, which you love.

[B]

Yeah.

[C]

A fight breaks out, and a guy named Jake Robles was a death row employee, and he was a blood and a close friend of Suge Knight. He was shot and killed, and witnesses were like, sean Combs, bodyguard, is the one who did it.

[B]

Right. So this is not good. This does not help this rivalry at all. And eventually, I guess, over the same time, Tupac's still in prison, but Suge Knight is still visiting Tupac there. And like they're becoming closer and closer because not only is Suge Knight going out of his way to go visit Tupac in prison, he's also helping him financially, helped him post bail to get out on an appeal. And when Tupac gets out of prison again, he's now deeply indebted to Suge Knight. But apparently they were. They had become real friends. He releases his fourth album, All Eyes on Me, I think it was In February of 1996, like immediately went double platinum. I think it went to number one on the charts.

[C]

So at this time, Death Row is at Can AM Studios outside la. That's what they're working out of. And people, you know, at the time were like, you know, the real stuff is going down there. There's a big gangster culture in and around that studio. Suge Knight is, is a real heavy.

[B]

He's.

[C]

He's threatening people right and left if they don't, you know, aren't on his good side. And people are hanging out there with gang members who are their security. So there's, you know, there might be Bloods there one day, there might be Crips there one day, there might be a huge singer there one day recording. But all of this is sort of happening around Can AM Studios, right?

[B]

So Tupac gets out of prison and remember, like, this guy's like essentially a heat seeking missile focused on Biggie Smalls. Like, I get the impression that he just sat in prison, like, ruminating about Biggie Smalls and getting back at him. So one of the first things he does was hire Biggie Smalls wife, Faith Evans, who was herself a pretty popular recording artist at the time. He offered her $25,000 to be on one of his records, a track for his album All Eyes on Me. And she did. She's like, sure, 25 grand, I'll do it. And I guess after she performed, or laid down the track, I guess as it's called, he was like, I got my check at the hotel room. You got to come over to my hotel room to get it.

[C]

Red flag.

[B]

Yeah. So she went. Both of them say that he propositioned her. He says that they had sex. She has repeatedly denied and emphatically denied that they did. But just the fact that they were in a hotel room together gave Tupac, even if it wasn't true that they had sex, gave him plenty of grounds to tell everybody that they did have sex, to at least gnaw at Biggie Smalls with Questions, you know, in his head.

[C]

Yeah. And this is his wife. So, like, it's on for real at this point. There's no coming back at the Soul Train Awards show. This is in March of 96. Tupac and Biggie both won awards. So they were there. That was the first time they had been together since that Quad Studio shooting, which is where it all started. And they both had their guys with them. They both had their entourages. Tupac had the Bloods. Biggie had the Southside Crips on his side. And there was a guy named Keith D, and he was a Crip, so he was with Biggie. And outside of this, at the Soul Train Award show, they got into a fight, basically. Witnesses said that Tupac is shouting down Biggie's groups, sort of inciting them. They all brandish guns, but nothing happens at this point. Just a lot of sort of back and forth and, like, you know, I've got my gun, so shut up.

[B]

Yeah, it's astounding. Crips and Bloods with their guns drawn in the same spot and no one shot anybody. That's crazy. So Tupac released Hit Em up, which is considered one of the best diss tracks of all time. He actually specifically names Biggie by. Well, by name. He also talks about how he slept with Biggie's wife, Faith Evans. Yeah, and while this is also going on, there's, like, a lot of money to. That people have figured out we can make from this, right? Like, this beef and, like, say, you know, some street skirmishes or whatever. This stuff makes news, right? Like, people know about this. And this is before, I think cell phones were still kind of bricky at the time, long before the Internet, like. And people still knew about this stuff. It was just a big deal. And that helped sell records like crazy. It also helped sell magazines. There's a vibe magazine from September 1995, and on the COVID is Biggie Smalls and Sean Combs. And it talks about east versus West. Some people put their finger on that Vibe issue and point to it as, like, fanning the flames of this beef and essentially making these. These two groups, like, have to hate each other even more or else they're going to seem weak or, like, you know, fake, whatever.

[C]

Yeah, for sure. And while this is all going on, Tupac is becoming a little more paranoid about Death Row Records and Suge Knight. And basically, like, Suge Knight's kind of controlling the money, saying that, you know, you're gonna blow all your money unless I'm in control. He didn't think he was getting the proper royalties. He thought, you're holding. Holding me back in Hollywood, and I'm trying to get my movie career going. So, like, trouble is sort of brewing on the inside there. Which finally would culminate on September 7, 1996. A lot of people connected with Death Row records. Tupac, you know, as one of them, went to the Mike Tyson fight against Bruce Seldon in Las Vegas. And after the fight, one of the Death Row group members, he was a blood named Trevon Lane, saw a guy who said, hey, he stole a Death Row necklace from me a few months ago. That guy's name was Orlando Anderson. He was a Crip and a nephew of Keef D and Tupac. Suge Knight and other people jump. Anderson rough him up pretty good. And a few hours later, Suge Knight and Tupac are at a stoplight. Cadillac pulls up next to them, and the car is shot up and Tupac is dead six days later at the age of 25.

[B]

Yeah, apparently he was, like, making jokes and everything as he was being put onto the gurney after the shooting, but he just went downhill really quick from there.

[C]

Yeah.

[B]

So a lot of people are like, this is Biggie. This is Sean Combs. They had. They said they had nothing to do with it, but this, this. This did kind of give Biggie Smalls, like, a wide opening to be like, this stuff has to stop. These. This East Coast, west coast thing has gotten out of hand. And it seemed pretty cut and dry that really it was them beating up Orlando Anderson and him and other Crips being in town who targeted and carried out this, this drive by, you know, that seems like almost certainly the explanation for the whole thing.

[C]

Yeah, I mean, that's who the cops thought from the very beginning. It was the guy that was jumped and beat up. They didn't arrest him. He died a couple of years later in a shooting in Compton. Fast forward all the way to 2019 in a memoir where Keefe D admitted that he was in that Cadillac. He said, I gave the gun to Anderson. He was in the backseat. There were two other guys in the car. Some people say it was a guy named DeAndre Smith who was the actual trigger man. But basically everyone in that car ended up being killed except for Keef d. And in September 2023, he was arrested and charged with Tupac's murder. And that trial is going to happen all these years later, coming up this summer in August of 2026.

[B]

Yeah, and Keef D. And later on a bad boy co founder named Kirk Burrows. And others. After all these allegations and revelations about what Sean Combs has been up to came out, they've come forward and been like, we think he actually did have something to do with this. Seems like a pretty quick turnaround to me. I think it was just Crips retaliating for a beat down. So Tupac is gone now, like you said, age 25. And if you want, you can go. You know where Clarkson is, Chuck?

[C]

Uh, sure. That was a rival high school of Redan.

[B]

There is a Tupac statue and memorial in Clarkston. Did you know that?

[C]

I did. I've never seen it though.

[B]

We went there. You mean I went there and it's pretty. It's pretty amazing. And it's just in the middle of this little rinky dink suburb of Atlanta. Strange, but it's cool.

[C]

That was kind of my stomping grounds was that area of Memorial Drive where Clarkston was owned.

[B]

Oh, yeah, yeah. Well, we'll have to go to the Tupac statue together sometime.

[C]

I'll go check it out.

[B]

So. So I think what, Chuck? Like less than six months? No, right. At about six months after Tupac was killed, Biggie Smalls was murdered.

[C]

Yeah. This was March 1997. He was in a car, riding in a car, leaving a party of vibe magazine in LA, pronounced dead at the hospital. He was but 24 years old. And immediately everyone was like, this is Suge Knight, who, by the way, people blamed Tupac shooting initially on Suge Knight. Yeah, but. But he was shot as well. He was just grazed, but that seems obviously to have not been the case. But everyone immediately was like, no, Suge Knight definitely was in on Biggie's murder.

[B]

In retaliation for Tupac shooting. Right?

[C]

Yeah.

[B]

It's also entirely possible that Sean Combs did this too, but it certainly seems to have been a contract hit. Like they, the, the people who killed Biggie Smalls shot and shot into his car. They were lying in wait. They were essentially parked at this intersection, waiting for them to stop. They stopped. Sean Combs car ran a red light and Biggie's car stopped at it. So Sean Combs wasn't near the shooting when it happened. There was an FBI agent who came forward, or actually, I guess, created a whole report on this, who is like this. It was essentially the LAPD hiring a hitman at the behest of either Suge Knight or Sean Combs. And so it was not Tupac's, probably was not a conspiracy. Biggie Smalls murder was almost certainly a conspiracy.

[C]

Yeah. And you know, Suge Knight Would have done all this from jail. He was in jail at the time. He is in jail. He's in prison now. Again, this is from. This is a 28 year sentence. So this is a big one. And this is for the death of a. A Compton businessman from 2015. He was never charged in Biggie's killing, but Biggie's last record or last, you know, sort of official release. I know they both put out a lot of stuff posthumously, but his next, like, real drop was Life After Death. It was called that before he was murdered. But that sold more than 10 million copies in certified diamond.

[B]

Yeah, I guess. Tupac released nine posthumous albums. Seven of them went platinum.

[C]

Yeah.

[B]

Did you know Suge Knight has a podcast from jail called Collect Call?

[C]

That's a pretty good name for a podcast from prison.

[B]

Agreed. Yeah. You want to know what ended the East Coast west coast beef?

[C]

Oh, is that still not happening?

[B]

No, no, it ended fairly soon after this. Rap became more decentralized and groups like outkast came around. And the. The. Whether you were from the east coast or the west coast was watered down. It didn't matter nearly as much. So you can thank outkast for ending the east coast, west coast rivalry.

[C]

Yeah, because people are like, no one's got a beef with Big Boy and Andre.

[B]

No, everybody loves them for sure. Like, I. I know we sound maybe facetious. We are not being facetious right now.

[C]

No, my boy, I love Outcast.

[B]

One last thing. Apparently Michael Jackson assaulted Tupac once in a studio when Tupac insulted Quincy Jones's daughter.

[C]

Oh, Rashida. Or another one.

[B]

Another one. Not Rashida. I don't think it was Rashida. I don't know.

[C]

I wonder how that fight went.

[B]

It's a widespread rumor. And apparently also, you know, Biggie was on one of Michael Jackson's songs, like, doing his thing. Like legit doing his thing. It wasn't watered down for the radio or anything like that. And apparently Michael Jackson threw his lot in with Biggie and was not a big fan of Tupac and snubbed him once.

[C]

Oh, wow.

[B]

And apparently, in addition to beating him.

[C]

Up and everyone said no one cares. Put side here on Michael Jackson. You don't have that kind of cred.

[B]

No. Yeah, but it is a. Like, Biggie does a pretty good job on that song.

[C]

I'll have to check it out.

[B]

Okay. I think that's it, Chuck.

[C]

Man, we did it.

[B]

We did it. We made it through. Hopefully we didn't sound too ridiculous and dorky at any point, but we'll find out. Yeah, Chuck said. Yeah. It means it's time for listener mail.

[C]

Yeah, this is just kind of a nice email with some good suggestions. Hey, guys, My name is Josiah Brown. I live in 10, Tennessee. I've been a devoted fan since I was about 10 years old and I'm 20 now. My mom put me onto you guys, and I basically never stopped. So thanks, Mom.

[B]

Thanks, Mom.

[C]

I've been binge listening recently. I do that every so often. I've just been reminded of how wonderful the show is, and I just want to reach out and say thanks for providing some wonderful content and bringing the same big old smile to my face all these years. Keep up the good work, fellas. And that is Josiah B. And Josiah had a lot of good ideas, including Anne Frank, Oskar Schindler, Motown.

[B]

Okay.

[C]

I want to do Motown for sure. Mr. Rogers. I can't believe we haven't done that one yet.

[B]

We were going to, and then that Tom Hanks movie came out and kind of ruined it for a little while.

[C]

Yeah, I finally saw that on a plane recently.

[B]

What'd you think?

[C]

Did you see it? No, it was okay. In the Hindenburg. In that the Hindenburg. Hindenburg is going to be coming at some point in the not too distant future because we commissioned that article and it's. It's in the folder on the computer. So I definitely know we're going to get to that one.

[B]

Okay. Booyah. Who is that again? Josiah.

[C]

Josiah.

[B]

Thanks a lot, Josiah. That was a very nice email and thanks for all the great ideas. If we do any of them, hopefully we'll remember to credit you with them, right?

[C]

That's right. Except for the Hindenburg. Yeah, it's already in the bat.

[B]

Okay. If you want to be like Josiah and E, email in. We would love to hear from you. You can send it off to stuffpodcastheartradio.com.

[A]

Stuff you should know know is a production of iHeartRadio. For more podcasts, my heart radio, visit the iHeartRadio app, Apple Podcasts, or wherever you listen to your favorite shows. This is an iHeart podcast. Guaranteed Human.