Stuff You Should Know - The Ballad of Biggie and Tupac

Episode Date: January 22, 2026

Biggie Smalls and Tupac Shakur had a famous beef with one another in the mid-90s. It was so intense, it sparked an even wider rivalry between the East and West Coasts. In just a few years, both men had been murdered and the music world was changed forever.See omnystudio.com/listener for privacy information.

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Listen to How to Money on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, everybody. We're going on tour. We're going to be in Denver, Seattle, and San Francisco soon, and tickets are still available. That's right. In the next few days, actually,

We're going to be in Denver on Tuesday the 27th of January. We're going to be in Seattle the next night, our dear beloved Seattle. And then finally winding it up on Thursday the 29th in San Francisco as part of our sketch fest appearance. And you can get all the ticket and tour information at Stuff You Should Know.com. Isn't that right? It is right. And we love you, Denver, and we love you San Francisco too. That's right.

We love all you cities, and we've missed you, and we can't wait to be back. Welcome to Stuff You Should Know, a production of IHeart Radio. 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. Yeah.

But regardless, that's what we're talking about. 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 going to, because we're talking about the lies of these two guys who were in many ways, real gangsters. 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.

Nice COA, man. Yeah. 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, 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. of rap in the 1990s.

That was huge. It was the central focus of rap during basically that whole decade. Yeah. And sadly, would leave both of them dead from violence. 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 was brought about because of just sort of the, the lifestyle that went along with their careers, you know? Yeah, and a lot of people make a case that that lifestyle was essentially demanded by fans and the media. Yeah. And certainly fostered and nurtured by fans and 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 wrapped about, or else they would be fake baby gangsters sometimes. Or studio gangsters, even worse. Well, yeah. Yeah. 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. Yeah. I mean, I think hip hop more than other types of music, too, there's an expectation to be real.

Again, God, all these puns flying out of my mouth. Oh, from Hyat Cypress Hill? 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. 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 think that you can trace it back to one group, one duo essentially. Yeah, so we're going to tell you a little bit about Tupac in 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 Affinni 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 Lassain 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 essentially was always Tupac. 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? I did not. 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. 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, Lila 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. Yeah. And she said, you always have to wear that bandana around your head just so like you do because I love it. It looks super cool. I know we've also talked about this before, but he was a member of Digital Underground with Humpty Humpty Hum, 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, wrapped on some of their albums. Yeah. 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 poverty and crime are like in the black community. You know, he didn't go by Humpty Hump. What was his, what did you go by?

That was Shock G. I've heard them referred to in other songs as... Well, all right, aka Humpty Hump, so... Okay. Yeah, you weren't completely wrong. A little side. I would direct people to the MERS song, Risky Business, that features Humpty or Shock G.

It's a pretty cute little song. All right. 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. Mm-hmm. There was no other title that it could have possibly been than that. Yeah, for sure.

But the problem was, like, there was, he was keeping it real. So there was nothing in the studio that he was producing that could be played on the radio. Yeah. So it was an underground sensation, but publicly, most people had not heard of Tupac at that point. Yeah, for sure. Dan Quayle kind of gave him a little more press when he blamed that record, Tupacalyps now, on the show. 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. The one I've seen him, and I don't think I saw Juice. I didn't see Poetic Justice. I saw Above the Rim.

He was really good and Above the Rim. I never saw that one. Oh, that's a good one. You should see it. All right, we need to get together and have a Tupac watch party, I guess. Okay, let's do that. Yeah. 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. Yeah, I mean, like for real, he was involved in 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 that cops were 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 fans were concerned. 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, you know, leaving when he was two years old and became a welder in the United States. But her, his mom, you know, 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 Rimes, love Busta. And J-Z all went there. Yeah, I'm guessing. I wasn't able to find it, but I'm guessing they crossed paths may have been there at the same time. Yeah, I mean, Donald Glover would have gone to my high school had they not sent him to the School of the Arts. Oh, yeah? 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? He grew up in the same neighborhood, basically. And you're really good looking. You're really handsome. 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, I'm just not going to do that. Instead, you got in your car and shouted, Rutan High Rules and, like, laid rubber peeling out of the parking lot. Yeah, that's right. Sure. Danger Mouse went to my high school, too, though. Oh, yeah? Oh, I forgot about Danger Mouse.

Danger Mouse did that gray album with the Beatles and, Jay-Z, right? I don't know. We'll find out the hard way. So like you said, a lot of hip-hop artists are probably or probably were our 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. school. So he started selling drugs on the side, crack again, because this is the 80s, and eventually he 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. 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. Yeah. 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. 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 being an 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 Small. And they became paired up in the media. They hung out there, 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. 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 for Biggie Smalls.

Was that it? That's my take. Yeah. Okay. So he was Notorious Big Iggy officially. Everyone called him Biggie, of course. he had as 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? Yeah. We're at 1993. Tupac's already a star and Biggie's starting to come up. All right. We'll be right back. I'm John Paul.

For years, I was the poster boy of the conversion therapy movement, the ex-gay who married an ex-lesbian, and traveled the world telling my story of how I changed my sexuality from gay to straight. Once upon a time, I was on 60 Minutes, Oprah, the front cover of Newsweek. And you might have heard my story, but you've never heard the real story. So join me as I peel back the layers and expose what happens. to me in the midst of conversion therapy, to shine a light on what the X-game movement does to people, and the pain it continues to cause. I had lost 150 pounds because if I couldn't control my sexuality, I was going to control my weight. It sounded like, and this is the word I used, a cult. And as I look, too, at the harm I did from within it. Listen to Atonement, the John

Polk Story on the IHeart Radio app, Apple Podcast. or wherever you get your podcasts. What if mind control is real? If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings.

Can you hypnotize someone into sleeping with you? I gave her some suggestions to be sexually aroused. Can you get someone to join your cult? NLP was used on me to access my subconscious. NLP, aka neurolinguistic programming, is a blend of hypnosis, linguistics, and psychology. Fans say it's like finally getting a user manual for your brain. It's about engineering consciousness. Mind games is the story of NLP.

It's crazy cast of disciples and the fake doctor who invented it at a new age commune and sold it to guys in suits. He stood trial for murder and got acquitted. The biggest mind game of all? NLP might actually work. This is wild. Listen to Mind Games on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. New Year, new goals, and in this economy, a better money plan is more necessary than ever. I am Matt.

And I'm Joel. We are from the How to Money podcast. And every week, we help you to spend smarter, save more, and make sense of what's going on out there. If you want 2026 to be the year you finally feel in control of your money, we're here to give you the tools and advice to help you make it happen. Listen to How to Money on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. 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 he broke, was already a star. His star was established and still growing. Biggie was just starting to come up. He was 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 L.A.,

he stayed on Tupac's couch. That's right. He was, like I said, he was a, he kind of considered Biggie like one of his lieutenants at the time and definitely was a mentor. Biggie's debut came out and 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, no, man, you need to stick with that guy.

apparently Tupac wasn't a big fan of Combs but he said that I had a feeling he just didn't want to get into managing him. 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? Yeah. The problem was is Sean Combs, again, remember, inextricably linked BFF with Biggie, as far as the public's concern, was actually jealous of Biggie and Tupac's friendship. He wanted to be friends with Tupac. He was jealous that Bickey 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 really kind of came through to Sean Combs after a little while. And he started not liking Tupac. 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? It's been planted. 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, 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 wrapped a lot about, you know,

sort of like the lifestyle and the gangster stuff that he was doing. But also there was a lot of vulnerability on that first record, too. Yeah, yeah. 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 just to kind of set the scene, can we talk a little bit about the brief history of hip hop up to that point and how big of a deal it was when Ready to Die came out?

Sure. Because you said that the West Coast had kind of taken over from the East Coast, like from Slick and L.L. Cool J and all them, the ones who were coming up in the 80s. At the time that Biggie Small's record came out, everyone was all about Dr. Dre, Ice Cube, Snoop Dog, all these guys, like, that's where rap was. It was on the West Coast. So for somebody to come along and basically snatch that away and bring it back to New York, it was just a really big deal. And it took a rapper of the caliber of, um,

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. It essentially caused an earthquake in the rap world and tilted everything back to New York. 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, you know, 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 got to watch out. You should probably stay away from this guy because, 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. 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 Iana 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. 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. So we'll 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. 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. He was in a 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 Ianna 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. Yeah, and the thing that really kind of blew this whole thing up is Tupac said as much. She 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. 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 Hinchman 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 Hinchman 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 because he thought they were in on this attack. And that's when the beef like really started between these two.

Yeah, and 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. Like he knew that it was going to happen and he didn't warn him. There's no evidence whatsoever. Either one of those things happened. Yeah. And Biggie Smalls always was 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's 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's side, and Crips hung out with Biggie's side. Yeah. 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. 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's found guilty of sexual assault. He's acquitted on the other charges, and he 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. Dude, if you want CRED, release your rap album while you're in prison. Yeah, called Me Against the World. Yeah, exactly. Yeah.

So while Tupac was in jail, I don't remember how long he was in for. 18 months. 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 Tupon This is all in Tupac's head. Like this whole East Coast 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 acknowledgement or belief that he was suffering from substantial mental health issues while he was alive. And that had a huge impact on the way that he interacted with people.

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 of a sudden, like, you were his enemy. Like, you would do something like set him up or rob them or pay for him to be killed or something. Yeah, I wondered about that. I'm glad you looked into that. Thank you. I am too.

You're welcome. Maybe we should take another break? Yeah. All right. We'll take another break and we'll get back to it right after this. I'm John Polk. For years ago I was the poster boy of the conversion therapy movement. The ex-gay who married an ex-lesbian and traveled the world telling my story of how I changed my sexuality from gay to straight.

Once upon a time I was on 60 minutes, Oprah. the front cover of Newsweek. And you might have heard my story, but you've never heard the real story. So join me as I peel back the layers and expose what happened to me in the midst of conversion therapy to shine a light on what the X-game movement does to people

and the pain it continues to cause. I had lost 150 pounds because if I couldn't control my sexuality, I was going to control my weight. It sounded like, and this is the word I used, a cult. And as I look too at the harm I did from within it. Listen to Atonement, the John Polk story on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What if mind control is real? If you could control the behavior of anybody around you, what kind of life would you have?

Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings. Can you hypnotize someone into something? sleeping with you? I gave her some suggestions to be sexually aroused. Can you get someone to join your cult? NLP was used on me to access my subconscious. NLP, aka neurolinguistic programming,

is a blend of hypnosis, linguistics, and psychology. Fans say it's like finally getting a user manual for your brain. It's about engineering consciousness. Mind games is the story of NLP. It's crazy cast of disciples and the fake doctor who invented it at a new. age commune and sold it to guys in suits. He stood trial for murder and got acquitted.

The biggest mind game of all, NLP, might actually work. This is wild. Listen to mind games on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. New Year, new goals, and in this economy, a better money plan is more necessary than ever. I am Matt, and I'm Joel. We are from the How to Money podcast, and every week we help you to spend smarter, save more, and makes sense of what's going on out there. If you want 2026 to be the year you finally feel in control of your money,

we're here to give you the tools and advice to help you make it happen. Listen to How to Money on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. All right. All right. So, I don't niggins. 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 Shug Knight, spelled S-U-G-E. He was the CEO of Death Row Records. Yeah. And he was a blood. Like, he was, you know, he was a straight-up blood from South Central Los Angeles. Yeah.

So, and he's now the CEO of Death Row Records, right? So that automatically makes Death Row Records like another. It's a 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 former blood, a blood. Yeah. So we talked about how the quad studio shooting, like really kind of started the beef.

Yeah. The thing that made that beef really genuinely public came at the award show for Source magazine, their annual awards. This time, this one was in 1995, where Shug Knight, who'd been visiting Tupac in jail and apparently had bought into Tupac's theory that Shubh Sean Combs and Biggie Smalls had set him up to be shot and robbed. Shug Knight was accepting an award. And during his speech, he invited 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.

He said, come on over to death row records. And, I mean, if you go back and look at Biggie Small's 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. Usually with his shirt wide open. Yeah, yeah. He really was not, he was not what they, like, death row records was doing.

And so, like, Shug Knight made it 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. Yeah. While you're accepting an award, it was a big deal. That really kind of made that beef public, and it turned into East Coast versus West Coast essentially immediately. 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&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. Yeah. 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 a talented artist. No. Because he wasn't, I guess, you know, he was a, like he said, an executive and a producer. And I was, I remember thinking they're like, why is he always throwing himself in there in front of the camera? Like, he sucks. Yeah, and he was dorky even compared to who were essentially mainstream rap artists like Tupac and Biggie Smalls. Oh, yeah. 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 more cringy, right? Yeah, for sure. He was. And he definitely, like, kind of brought down the credibility 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. Yeah, absolutely. 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. What about you? As the greatest rapper of all time? Well, it's between Tupac and Biggie. How about that? Oh, okay. Because Chuck D. like dead in the bullseye for me. Oh yeah? Oh yeah. Okay. I was always a public enemy guy.

Like that started in high school. 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 raw, edgy for me. Yeah, I liked it. I mean, trust me, I was way more into like the Tribe Call 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. Yeah, but I mean. As I was listening to The Smiths and the Cure. That's right. No, I'm with you. I was listening to Smith and the Cure, but also like Boot Camp Click,

like Smith and Weston. Nas, Wutang, gangstar. Yeah. See, I never, I like Gangstar, but I never got into Wu Tang. They were pretty good. They were better solo, I think. Most of, like Method Man and Rizzo were better solo.

have been muting together, but whatever. And this is two middle-aged white guys discussed their hip-hop paths. I do. I do have to say that Dr. Draze Zachronic was literally life-changing. Oh, for sure. And it's not just me that that happened to.

I think that changed a lot of people's trajectory. I was one of them, man. I know that thing by heart inside and out. Yeah. It's a fun listen when I put it on. A lot of nostalgia floods back. It is. I thought the same thing would be for doggy style, Snoops.

debut solo album. It does not hold up. Yeah, I mean, it's not, it wasn't as good as the chronic no mile. But I liked it as much as the chronic at the time. I don't anymore. Yeah, I'm with you. And part of that may have to do with the fact that Snoop Dog has, I don't know, become the Snoop Dog of today. Man, he's amazing. He's now the owner of Do Throw Records. No, he's awesome. But I just feel like he's, he's a bit overexposed for my taste. Oh, I see. He's like the, um, uh, The Peyton Manning of the hip-hop world. He's the Pedro Pascal of rap. Okay, even better said.

But he's an American treasure, though. I mean, like, he's an Olympic mascot, along with Flavor Flav. Now I'm picturing Snoop Dog, Pedro Pascal, and Peyton Manning, and just sitting at lunch just saying, like, guys, isn't this great? I could see that. Talking about mutual funds. Yeah, we should do something together because we're done out there enough. Right.

It'll blow everyone's mind. All right. So we are in September 1995 at this point. Shug 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. Yeah. A fight breaks out. And a guy named Jake Robles, it was a death row employee, and he was a blood and a close friend of Shug Knight, he was shot and killed. And witnesses were like, Sean Combs' bodyguard is the one who did it. 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 Shug Night is still visiting Tupac there. And like, they're becoming closer and closer. because not only is Shug Night 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 Shug Knight, but apparently they had become real friends. He releases his fourth album, All Eyes on Me.

I think it was in February of 1996, like immediately it went double platinum. I think it went to number one on the charts. So at this time, Death Row is at Can Am Studios outside L.A. That's what they're working out of. And people, you know, at the time, we're like, you know, the real stuff is going down there. There's a big gangster culture in and around that studio.

Shug Knight is a real heavy. 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 Canem Studios. Right. So Tupac gets out 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 Small's 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 is it called, he was like, I'll, I got my check at the hotel room. You got to come over to my hotel room to get it. Red flag. Yeah. So she went, both of them say that he propositioned her. He says that they had sex. She is 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. And that in their head. 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 Award 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, shouting down Biggie's groups, sort of inciting them. They all brandished 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.

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 disc tracks of all time. He actually specifically names Biggie, 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 that people have figured out we can make from this, right?

Yeah. This beef and like, say, you know, some street skirmishes or whatever, this stuff makes new. 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, and people still knew about this stuff. It was just a big deal. And that helps sell records like crazy. It also helps sell magazines. There's a Vibe magazine from September 1995. And on the cover is Biggie Smalls and Sean Combs. And it talks about East versus West. Some people put their 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 yeah for sure and while this is all going on Tupac is becoming a little more paranoid about death row records and Shug Knight and basically like Shug Knight's kind of controlling the money saying that you know you're going to

blow all your money unless I'm in control uh he didn't think he was getting the proper royalties uh 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 uh which finally would culminate on September 7th 1996 uh a lot of people connected with death throw records uh Tupac you know as one of them went to the Mike Tyson fight against Bruce Selden 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 for me a few months ago.

That guy's name was Orlando Anderson. He was a Crip and a nephew of Keith D. And Tupac Shug Knight and other people jump Anderson, rough him up pretty good. And a few hours later, Shugnight 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. 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. Yeah. So a lot of people are like, this is Biggie. This is Sean Combs.

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 um 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. Yeah, I mean, that's who the cops thought from the very beginning 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 Keith D.

Admitted that he was in that Cadillac. He said, I gave the gun to Anderson. He was in the back seat. There were two other guys in the car. Some people say it was a guy named D'Andre Smith, who was the actual trigger man. But basically everyone in that car ended up being killed except for Keith 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. Yeah, and Keith D and later on, a bad boy co-founder named Kirk Burroughs and others, after all these allegations and revelations about what Sean

Holmes has been up to came out. They 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 Cripps 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 Clarkston is, Chuck? Sure.

That was a rival high school of Redan. There is a Tupac statue in Memorial in Clarkston. Did you know that? I did. I've never seen it, though. We went there. You mean I went there, and it's pretty amazing. And it's just in the middle of this little rinky dink suburb of Atlanta.

It's strange, but it's cool. That was kind of my stomping grounds, was that area of Memorial Drive where Clarkston was owned. Oh, yeah? Yeah. Well, we'll have to go to the Tupac statue together. All right. I'll go check it out. So I think what, Chuck, like less than six months?

No, right at about six months after Tupac was killed. Biggie Smalls was murdered. Yeah, this was March 1997. He was in a car, riding in a car, leaving a party of Vibe magazine in L.A., pronounced dead at the hospital. He was but 24 years old. And immediately everyone was like, this is Shug Knight, who, by the way, people blamed Tupac shooting initially on Shug Night. Yeah. But he was shot as well.

He was just grazed, but that seems obviously to have not been the case. but everyone immediate was like, no, Shug Knight, it definitely was in on Biggie's murder. In retaliation for Tupac shooting, right? Yeah. It's also entirely possible that Sean Combs did this too, but it certainly seems to have been a contract hit. Like the people who killed Biggie Smalls 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. 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 was like, it was essentially the LAPD hiring a hitman at the behest of either Shug Knight or Sean Combs. And so it was not, Tupac probably was not a conspiracy. Biggie Small's murder was almost certainly a conspiracy. Yeah, and, you know, Shug 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 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, like, after death. It was called that before he was murdered. But that sold more than 10 million copies

and certified diamond. Yeah, it gets not as Tupac released nine posthumous album, seven of them went platinum. Yeah. Did you know Shug Knight has a podcast from jail called Collect Call? It's a pretty good name for a podcast from prison. Agreed. Yeah. You want to know what ended the East Coast, West Coast beef? Oh, is that still not happening? No, no, it ended fairly soon after this. Rapp became more decentralized, and groups like Outcast came around. And 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 Outcast for ending the East Coast West Coast rivalry. Yeah, because people are like, no one's got a beef with Big Boy and Andre. No, everybody loves them for sure. Like I know we sound maybe facetious. We are not being facetious right now. No. But boy, I love that guest. Um, one last thing. Apparently Michael Jackson assaulted Tupac once in a studio when Tupac insulted, um, Quincy Jones's daughter.

Oh, uh, uh, uh, Rashida or another one? Another one, not Rashida. I don't think it was Rashida. I don't know. I wonder how that, I wonder how that fight went. It's a widespread root. And apparently also, you know, Biggie was on one of Michael Jackson's songs. Oh, really?

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. Oh, wow. And apparently in addition to beating him up. And everyone said, no one cares. Put side here on Michael Jackson.

You don't have that kind of cred. No. Yeah. But it is a, like, he does a pretty good job on that song. I'll have to check it out. Okay, I think that's it, Chuck. Man, we did it. 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, me. Yeah, this is just kind of a nice email with some good suggestions. Hey, guys, my name is Josiah Brown. I live in Tennessee. I've been a devoted fan since I was about 10 years old, and I'm 20 now.

Wow. My mom put me on to you guys, and I basically never stopped. So thanks, Mom. Thanks, Mom. 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, Oscar Schindler, Motown. Okay. I want to do Motown for sure. Mr. Rogers? I can't believe we haven't done that one yet. We were going to, and then that Tom Hanks movie came out and kind of ruined it for a little while.

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

Okay. Boo-ya. Who is that again? again, Josiah? Josiah. 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? That's right.

Except for the Hindenburg. Yeah. It's already in the bat. Okay. If you want to be like Josiah and email in, we would love to hear from you. You can send it off to Stuff Podcast at iHeartRadio.com. Stuff you should know is a production of IHeartRadio. For more podcasts to My Heart Radio, visit the Iheart Radio app.

Apple Podcasts are wherever you listen to your favorite shows. What if mind control is real? If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings. Can you hypnotize someone into sleeping with you? I gave her some suggestions to be sexually aroused. Can you get someone to join your cult?

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