Transcript

The Ballad of Biggie and Tupac | STUFF YOU SHOULD KNOW

From Stuff You Should Know · Episode page · Watch on YouTube

· 51 min · 9,649 words · 175 timestamped sections

This is the full, timestamped transcript of "The Ballad of Biggie and Tupac | STUFF YOU SHOULD KNOW", an episode of Stuff You Should Know published January 24, 2026 (51 min, about 9,649 words). It mentions 34 people, works and ideas, including Biggie Smalls, Hip-Hop, Tupac Shakur, Death Row Records, Shan Diddy Combmes.

What this episode is about

The discussion explores the notorious rivalry between hip-hop legends Biggie Smalls and Tupac Shakur, delving into their lives marked by violence, crime, and tragedy. The episode addresses the complexities of their relationship and the broader implications of their impact on the hip-hop culture of the 1990s, while also issuing a content warning for mature themes.

Key takeaways

  • Denver, Seattle, and San Francisco: where hip-hop legends meet tour buses and eager fans—grab your tickets now!
  • Biggie and Tupac's rivalry wasn't just beef; it was the catalyst for a rap culture war that ignited the '90s.
  • In hip-hop, authenticity is currency—leasing a persona can cost artists their lives and legacies.
  • Tupac's roots in activism show that even artists can be shaped by the social issues surrounding them—revolutionary complexity.
  • Despite their fame, both legends were victims of the lifestyles glorified by fans—a cautionary tale for future artists.

Who speaks in this episode?

What is discussed, and when

  1. – 5:00: Hip-Hop, San Francisco, Biggie Smalls, Tupac Shakur
  2. – 10:00: Hip-Hop, New York, New York, San Francisco, Thug Life
  3. – 15:00: Biggie Smalls, Hip-Hop, Bad Boy Records, Shan Diddy Combmes
  4. – 20:00: New York, New York, West Coast, Ready to Die, Biggie Smalls
  5. – 25:00: Haitian Jack, New York, New York, Ayanna Jackson, Jimmy Henchman Roseman
  6. – 30:00: Biggie Smalls, Death Row Records, Shan Diddy Combmes, Suge Knight
  7. – 35:00: Biggie Smalls, Hip-Hop, Death Row Records, Shan Diddy Combmes
  8. – 40:00: Suge Knight, Biggie Smalls, All Eyes on Me, Faith Evans
  9. – 45:00: Biggie Smalls, Death Row Records, Orlando Anderson, Suge Knight
  10. – 50:00: Shan Diddy Combmes, Suge Knight, Biggie Smalls, East Coast

Notable quotes from "The Ballad of Biggie and Tupac | STUFF YOU SHOULD KNOW"

  • Yeah. We're talking about Biggie and Tupac, and we want to issue a warning and a trigger warning. Not no pun intended there, but this one's obviously going to because we're talking.
    about Biggie Smalls · at
  • 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…
    about West Coast · at
  • 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.
    about Hip-Hop · at
  • Other unsigned rappers, which eventually landed him on the ears of a 23-year-old named Shawn Combmes.
    about Shan Diddy Combmes · at
  • 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…
    about Haitian Jack · at
  • Future. but it was basically hip-hop labels. You had Bad Boy with Shawn Combmes, Death Row Records on the other side. that company was founded about the same time in 1992 by…
    about Death Row Records · at
  • Tupac are at a stoplight. Cadillac pulls up next to them and the car is shot up and Tupac is dead 6 days later at the age of 25.
    about Tupac Shakur · at
  • Yeah. that's who the cops thought from the very beginning. it was the guy that was jumped and beat up.
    about Orlando Anderson · at

Who and what is mentioned in this episode?

People

  • Biggie Smalls — Person · Primary subject (other half of core rivalry) · 22 mentions · first at
    The episode traces his rise in NYC rap, relationship with Sean Combs/Bad Boy, friendship-turned-feud with Tupac, and his 1997 murder.
  • Tupac Shakur — Person · Primary subject (one half of core rivalry) · 2 mentions · first at
    Central figure in the episode’s narrative: his upbringing, legal troubles, paranoia, and escalation of the East Coast/West Coast conflict culminating in his 1996 murder.
  • Shan Diddy Combmes — Person · Key referenced industry figure (Bad Boy executive) and alleged antagonist · 13 mentions · first at
    Presented as Biggie’s label boss and public counterpart in the East/West label rivalry; discussed as jealous of Tupac/Biggie friendship and later subject of allegations around violence.
  • Suge Knight — Person · Key referenced industry figure (Death Row CEO) and escalation catalyst · 12 mentions · first at
    Depicted as Death Row’s CEO, aligned with Tupac, publicly antagonizing Combs/Bad Boy, and central to the atmosphere of violence and intimidation around the feud.
    Dr. Dre and a few other guys. And one of those guys was his former bodyguard, Marian Suge Knight. spelled s u g- e.
  • Orlando Anderson — Person · Referenced suspect/retaliation target in Tupac murder narrative · 2 mentions · first at
    Portrayed as the man beaten by Tupac/Death Row associates in Las Vegas shortly before the shooting; later framed as likely shooter or key participant.
  • Haitian Jack — Person · Referenced street figure tied to Tupac’s legal troubles · 7 mentions · first at
    Introduced as a dangerous associate in NYC; linked to the Ayanna Jackson case and to Tupac’s belief he was set up, intensifying paranoia and conflict dynamics.
  • Ayanna Jackson — Person · Referenced complainant in Tupac legal case · 2 mentions · first at
    Her allegation is a pivotal plot point: it triggers Tupac’s criminal charges and fuels his belief he was set up, affecting subsequent relationships and escalation.
    Haitian Jack, but that, we need to point out that completely contradicts the story of the victim from Ayanna Jackson. So, but the whole point of this is there's like you said, there's now this official beef that kind of again planted the.
  • Apheni Shakur — Person · Referenced family member shaping Tupac’s origin story · 1 mention · first at
    Mentioned as Tupac’s mother and a Black Panther Party figure; used to contextualize his naming, politics, and early life circumstances.
    As far as Tupac goes, he was born in 1971, same year as me. He was born in Harlem. his mother was Apheni Shakur and she was one of the Panther 21. I'm pretty sure we talked about them in the Black Panther episode.
  • Christopher Wallace — Person · Alternate/legal name reference for Biggie · 1 mention · first at
    Used to identify Biggie Smalls’ birth name and background; helps disambiguate the stage name from the person.
    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…
  • Faith Evans — Person · Referenced expert · 3 mentions · first at
    Biggie Smalls' wife and a recording artist, involved in the narrative of the East Coast vs. West Coast rivalry.
    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.
  • Jimmy Henchman Roseman — Person · Referenced expert · 2 mentions · first at
    A figure involved in the hip-hop scene, connected to the events surrounding Tupac's shooting.
    He knew Shawn Combmes. He knew Haitian Jack and he said, Hey, Tupac, why don't you do a guest spot on for this rapper Little Shawn? he's in Biggie Circle. He's a guy with Shawn Combmes as well. we'll pay you seven.
  • Dan Quayle — Person · Referenced expert · 1 mention · first at
    Mentioned in passing in relation to Tupac Shakur's early career.
    Yeah, for sure. he Dan Quail kind of gave him a little more press when Yeah.

Books & papers

  • Ready to Die — Book · Referenced work · 3 mentions · first at
    Biggie Smalls' debut album, which brought hip-hop back to the East Coast and went double platinum.
    Was a he kind of considered Biggie like a one of his lieutenants at the time and definitely was a mentor. Biggiey's debut came out and it was called Ready to Die in 1994.
  • All Eyes on Me — Book · Referenced work · 3 mentions · first at
    Tupac Shakur's fourth album, released after his prison sentence, which went double platinum.
    Deeply indebted to Suge Knight, but all 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…
  • Hit 'Em Up — Book · Referenced work · 4 mentions
    A diss track by Tupac Shakur targeting Biggie Smalls, considered one of the best diss tracks of all time.
    So Tupac released Hitim 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 Biggiey's.
  • Me Against the World — Book · Referenced work · 1 mention · first at
    Tupac Shakur's third album, released while he was in prison, which contributed to his 'thug' image.
    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…

Companies & orgs

  • Death Row Records — Company · Business focus · 6 mentions · first at
    Central to the East Coast vs. West Coast hip-hop rivalry, associated with Tupac Shakur and Suge Knight.
  • Bad Boy Records — Company · Business focus · 1 mention · first at
    Associated with Biggie Smalls and Sean Combs, central to the East Coast side of the hip-hop rivalry.
    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,.
  • Vibe Magazine — Company · Referenced expert · 2 mentions · first at
    A magazine that covered the East Coast vs. West Coast rivalry and hip-hop culture.
    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 cover is Biggie Smalls and…
  • Digital Underground — Company · Referenced expert · 1 mention · first at
    Early association of Tupac Shakur, where he started as a dancer and later rapper.
    Famous Humpty Dance and 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.
  • Outcast — Company · Referenced expert · 1 mention · first at
    A hip-hop group credited with helping to end the East Coast vs. West Coast rivalry.
    So, you can thank Outcast for ending the East Coast West Coast rivalry.

Concepts & topics

  • Hip-Hop — Concept · Core topic · 13 mentions · first at
    The genre of music at the center of the episode's discussion, particularly its cultural and regional divisions.
  • West Coast — Concept · Core topic · 10 mentions · first at
    Represents the other side of the hip-hop rivalry, associated with artists like Tupac Shakur and Death Row Records.
  • East Coast — Concept · Core topic · 7 mentions · first at
    Represents one side of the hip-hop rivalry, associated with artists like Biggie Smalls and Bad Boy Records.
    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…
  • Gangster — Concept · Key argument · 5 mentions · first at
    Describes the lifestyle and image associated with many hip-hop artists during the 90s, including Tupac and Biggie.
    Guys. and just super sad that was, brought about because of just sort of the lifestyle that went along with their careers, you know.
  • Thug Life — Concept · Key argument · 1 mention · first at
    A philosophy and lifestyle associated with Tupac Shakur, representing the 'gangster' image in hip-hop.
    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…
  • Black Panther Party — Concept · Referenced expert · 1 mention · first at
    Tupac Shakur's mother was a member, influencing his upbringing and political views.
    1971, same year as me. He was born in Harlem. his mother was Apheni Shakur and she was one of the Panther 21. I'm pretty sure we talked about them in the Black Panther episode.

Places & events

  • New York, New York — Place · Setting · 9 mentions · first at
    Birthplace of Biggie Smalls and a central location in the East Coast hip-hop scene.
    So, I usually think I associate Tupac with New York because pretty much all the movies he has was ever in were all set in New York, but he's from San Francisco. he was born in.
  • San Francisco — Place · Setting · 3 mentions · first at
    Where Tupac Shakur grew up and a significant location in his early life and career.
    We're going to be in Denver, Seattle, and San Francisco soon. And tickets are still available.
  • Harlem — Place · Setting · 2 mentions · first at
    Birthplace of Tupac Shakur, a significant location in his early life.
    Happened from there. But, for as far as Tupac goes, he was born in 1971, same year as me. He was born in Harlem. his mother was Apheni Shakur and she was one of the Panther 21.…
  • Marin County — Place · Setting · 1 mention · first at
    Where Tupac Shakur lived during his early years, a suburb of San Francisco.
    Involved in a shoot 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.
  • Clarkston — Place · Setting · 2 mentions · first at
    Location of a Tupac Shakur statue and memorial, mentioned in the podcast.
    There is a Tupac statue in memorial in Clarkston. Did you know that?

Media & podcasts

  • Poetic Justice — Media · Referenced work · 1 mention · first at
    A movie featuring Tupac Shakur, contributing to his early fame.
    Afterward in 1992 and 1993 he put out or he was in the movies Juice and Poetic Justice.
  • Juice — Media · Referenced work · 1 mention · first at
    A movie featuring Tupac Shakur, contributing to his early fame.
    Both really great movies. Juice is awesome actually. So is Poetic Justice. I love both of those movies.

Full transcript with timestamps

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 in the next few days, actually. Uh 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. Uh 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 stuffyou 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 oldfashioned 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 um regardless, that's what we're talking about.

Yeah. We're talking about uh Biggie and Tupac, and we want to issue a uh a warning and uh a trigger warning. Not no pun intended there, but uh this one's obviously going to because we're talking about the lies of these two guys uh who were in many ways u real gangsters. Um, a lot of stuff went down including uh sexual assault and uh gunplay and uh murder and it's uh you know it's probably not appropriate for 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 uh 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. It's referred to as a beef

um 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.

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

Yeah. And a lot of people make a case that there that lifestyle was essentially demanded by fans and the media

and certainly um 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 wrapped about um 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 I mean I think hip-hop more than other types of music too, there's an expectation to be uh to be real. Um again, God, all these puns flying out of my mouth.

Oh, from uh Cyber Hill. Yeah, of course. But uh to be real and like you said not you know if you were found out to be um sort of rapping about something and and really kind of uh fake

uh in real life like that that's no good for your career um as a hip-hop artist. So it's sort of you know they I don't know to me they 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 and they I mean they essentially laid the groundwork for that. Um, 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.

Yeah. So, uh, 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, uh, for

as far as Tupac goes, he was born in 1971, uh, same year as me. He was born in Harlem. Uh his mother was uh Apheni Shakur and she was one of the Panther 21. I'm pretty sure we talked about them in the Black Panther episode.

Uh but they were uh part of the Black Panther Party, the ones who were accused of uh carrying out a bombing campaign. Um she did win an aqu quiddle in court defending herself and exposed a lot of stuff about undercover cops and the tactics they use that were very unourred. Mhm.

But Tupac was born about a month after that trial and uh born Lasain Krooks. Uh but it's not like he changed his name to 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.

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

I did not. So, um I usually think I associate Tupac with New York because pretty much all the movies he has 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 Mering County, which is a suburb of San Francisco, um, pretty early on in his life. And at the time, his mom was, um, struggling with a crack addiction. So, Tupac was essentially on his own from a very young age. And, um, as black kids at the time in the 80s in particular did to make money, uh, when you were in a a situation like that, you he sold drugs and that's how he supported himself for a long time. uh while he was even going through school too.

Yeah. And he was um like we'll see Biggie was he was a really good English student and I bet a lot of hip-hop uh performers were good in English. You know, it just sort of makes sense. Uh but he dropped out of high school. Uh he studied poetry. He continued to after he dropped out. Uh and actually his teacher, his English teacher, one of them, uh Leela Steinberg was like, "Hey, I see a lot of uh 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 um that bandana around your head just so like you do cuz I love it."

It looks super cool. Um I know we've also talked about this before, but he was a member of Digital Underground with Humpty Hump of the famous Humpty Dance and 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 he he didn't go by Humpty Hump. What was his What did he go by? Uh that was Shock G.

I've heard him referred to on other songs as well. All right. aka Humpty Hump. So, yeah, you weren't completely wrong.

Um, a little a little aside, uh, I would direct people to the merge song, Risky Business, that features, um, Humpty or Shock G.

It's a pretty 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 Tupocalypse Now.

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 um 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. Uh he Dan Quail kind of gave him a little more press when Yeah.

Uh he blamed that record to Apocalypse Now on the shooting of a Texas state trooper. So he was in the news a little bit at least. Mhm.

Uh and he started acting kind of right afterward in 1992 and 1993 he put out um or he was in the movies uh Juice and Poetic Justice.

Uh both really great movies. Juice 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 think I saw Juice. I didn't see Poetic Justice. I saw um Above the Rim. He was really good in 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. Uh, but he started getting a little more famous uh sort of slowly and this is when kind of the early 90s at the very beginning of his career is when he first started uh getting into trouble and getting like a real reputation as uh sort of living that lifestyle.

Yeah. I mean like for real. He was involved in a shoot a shootout at the um Marin County Festival where he lived um where he had just performed that killed a six-year-old who was playing on a school ground nearby.

Yeah. Um he shot at offduty police in Atlanta in 1993 when he tried to prevent them from um beating up a black motorist. And those charges were thrown out because it turns out the 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 um 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 uh early days. Uh Biggie Smalls was born uh he's a little younger. He was born in 1972 in Brooklyn. His name was Christopher Wallace. Uh he was born to Jamaican immigrant parents and his mom was a preschool teacher. Um his dad was a politician in Jamaica but uh ended up you know leaving when he was 2 years old and became a welder in the United States.

Uh but her his mom you know Valetta 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- reggarded high school. Um, uh, and then later went to, uh, George Westinghouse Career in Tech Education High School,

which had quite an alumni base as far as hip-hop goes because DMX, Buster Rhymes, Love Buster, and Jay-Z all went there.

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.

Yeah. I mean, Donald Glover would have gone to my high school had they not uh 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 He's astoundingly good-looking. Uh and I wanted to go over and say like, "Hey, man. Uh we grew up in the same neighborhood basically."

And you're really good-looking. He really handsome, but he and I'm such a big fan of his, but uh from his music to his acting, but he was with his family and like was just like h I'm just not going to do that.

Instead, he got in your car and shouted, "We're Dan High rules." And like laid rubber peeling out of the parking lot.

Yeah, that's right. Uh sure. Danger Mouse went to my high school, too, though. Oh, yeah. Oh, I forgot about Danger Mouse. Danger Mouse did that um Gray album with the Beatles and um Jay-Z, right? Uh, I don't know.

We'll find out the hard way. So, uh, like you said, um, a lot of hip-hop artists are probably or probably were are good English students. And, um, Biggie Smalls was not an exception to that. Like Tupac, he was actually he excelled in English in high school. But also like Tupac, um, his family was not exactly wellto-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. Um 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.

Yeah. He ended up in jail actually. He spent nine months in jail at one point uh because he couldn't make bail. And once he got out uh he made a demo tape under the name Biggie Smalls. His nickname as a kid was Big. Uh, but I think that came from a a gangster in a movie from 1975 called Let's Do It Again. Biggie Smalls did.

Mhm. And he said that he wasn't trying to get into a career. He just sort of did it for fun.

And uh that got him on Source Magazine's uh list in 1992 of Unsigned in 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 uh named Shawn Combmes.

So, yeah, Shawn Combmes, Puff Daddy, Diddy. Um, 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 uh being a a entrepreneur and all sorts of other things, he decided to found his own um record company, Bad Boy Worldwide Music Group, uh 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.

Yeah. And his uh when he put out his first single, it was under the name Notorious B.I. uh because of legal issues, I guess, with the movie

for Biggie Smalls. Was that That's my take. Yeah. Okay. So, he was Notorious Big I officially. Everyone called him Biggie, of course. Uh he had as a kid in 93 with his high school girlfriend uh Jan Jackson, not Janet Jackson. And he hadn't really broken through at this point even though he was with uh Shawn Colmes at the time. Um but he, you know, so he continued to kind of deal drugs. Apparently Colmes was like, "You can't do that kind of stuff if you want to get anywhere." Uh but he broke up with his um high school sweetheart who he had his first kid with and a few months after after that ended up with Faith Evans who was also on the Bad Boy label and that is uh Biggie and his start. So good time for a break.

Yeah, we're at 1993. Tupac's already a star and Biggie is starting to come up. All right, we'll be right back. You should know.

So, uh, one of the things you may or may not know if you're just kind of passing passingly familiar with the beef between, um, Biggie and Tupac is that they started out as friends. They were actually pretty good friends for a while. Um, 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 a mentor to him. Um they met in 1993 and um they hung out with a bunch of other people, played around with a bunch of guns at Tupac's house and they they became close enough that whenever Biggie went out to LA, he stayed on Tupac's couch.

That's right. Uh he was, like I said, he was a he kind of considered Biggie like a one of his lieutenants at the time and definitely was a mentor. Uh, Biggiey's debut came out and it was called Ready to Die in 1994. And before that, uh, Biggie was like, "You know what? I think you should just be my manager and take over from, uh, take over for Shawn Colmes." And Tupac was like, "No, man. You need to stick with that guy." Um, apparently Tupac wasn't a big fan of Combmes.

Yeah. Uh, but, you know, he said that I 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 a manager or a label owner. Like, he was a performer.

And Sean Combmes 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 um Shawn Combmes, again, remember in 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 Bicki got to be friends with Tupac. The reason Tupac didn't care about um being friends with Shawn Combmes is that he thought Shawn Combmes was basically a poser. Um he was a record executive playing like he was a hardcore rapper

and um he didn't have much respect for him. And I think that that really kind of came through um to to Shawn Combmes after a little while and he didn't he started not liking Tupac. Yeah, that's right. Uh, so the beef is sort of the beef seed is planted as as they are. Uh, you know that old saying,

where's the beef seed? It's been planted. Exactly. Uh, Ready to Die, like I mentioned, was Biggiey's debut in '94. It was a big hit. It went double platinum uh about a year later. Uh, which is means a lot of records were sold. And this was when the West Coast was sort of, uh, 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. Uh, and it's a great record. He was, uh, you know, he he wrapped a lot about, um, 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. He um, 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. Um, and I just to kind of set the scene, can we talk a little bit about the the brief history of hiphop up to that that point and how big of a deal it was when um 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 Rick and LL CoolJ and all them the ones who were coming up in the 80s. At the time that um Biggie Smalls 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 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 were tons of other albums that had come out like Tribe Called Quest had three albums by this time. Um and yet the Biggie Smalls record coming out just just completely undid essentially caused an earthquake in the rap world and tilted everything back to New York.

Yeah, for sure. Uh so as this is happening and Biggiey's blowing up like in a big way, uh Tupac is in New York um 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 uh named Haitian Jack and he starts hanging out with Tupac. Tupac likes this guy. They start partying together. Uh 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 cuz like he's a super violent dude. Like, I know we're 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, um 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 um Tupac against Haitian Jack because shortly after that um 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 um Tupac Haitian Jack um the road manager for Tupac Charles Man Fuller and another man I couldn't find who he was um 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 um 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 um a beef now with Haitian Jack because he thought that Haitian Jack had dropped the dime on Tupac and to get out of the trouble for this gang rape um charge.

Yeah. So Haitian Jack had his case separated from Man Fuller and Tupac. Uh he pleaded down to a lesser charge. He pleaded guilty to two misdemeanors and avoided jail time. Mhm.

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 uh the story of the victim uh from Ayanna Jackson. So, uh but you know, the whole point of this is there's like you said, there's now this official beef that um kind of again planted the seed of what would happen to he and eventually Biggie moving forward.

Yeah. Yeah. And the thing that really kind of um 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 um 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. Uh so the case is moving forward at this point. Uh Tupac is financially strapped. Uh 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. Uh so there was an invitation from a guy named Jimmy Henchman Roseman.

Uh he knew Shawn Combmes. He knew Haitian Jack and he said, "Hey, Tupac, why don't you do a guest spot uh on for this rapper Little Shawn? Uh he's in uh Biggie Circle. He's a guy with Shawn Combmes as well. Uh we'll pay you seven grand." He needed the money, so he did it. Uh he shows up at Times Square uh at Quad Recording Studios on November 30th along with three of his guys. And before getting on the elevator uh to go up and record, they were met by these other three guys who draw guns, tell them to get down on the ground. Uh Tupac draws his gun and he ends up being uh shot. He ends up being robbed. He ends up being beaten pretty badly. And Combmes and Biggie and uh Henchman, Jimmy Henchman, Roseman were up in the studio at the time. Um they were they were there. So all of a sudden, Tupac is getting um wheeled out on a gurnie, sees those guys, and he flips a bird at Biggie and his crew cuz 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 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 um 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 it seems like it was a one-sided beef, but the beef on Tupac's side was so energetic that it 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 Biggiey's side.

Yeah. You 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 patched things up. That is not going to happen with with you now hanging around with the Crips and the Bloods.

Yeah. And no one ever really got to the bottom of uh who was behind that shooting. There's a lot of disagreement and people pointing fingers and claiming this and that. Uh I guess we don't need to totally get into that. But after he uh was beaten and shot and robbed, uh 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. Uh and he's sentenced to 18 months in prison. Uh where his third album came out, Me Against the World, came out while he was in prison serving that uh sentence. Dude, if you want cred, release your rap album while you're in prison.

Yeah. Called Me Against the World. Yeah, exactly. Yeah. Um, so while Tupac was in jail, I don't remember how long he was in for it.

18 months. 18 months. Okay. While he was in jail, um, Biggie releases a track called Who Shot You. And, um, 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 um that seems to not be the case at all. Biggie Smalls apparently wrote that song before the Quad City shooting. And um 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 west west west west west west west west west west west coast beef seems to have come from Tupac being paranoid essentially and I looked up why he might have been paranoid and um apparently there's pretty widespread acknowledgement 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 um 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.

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

You're welcome. Uh maybe we should take another break. Yeah. All right. We'll take another break and we'll uh we'll get back to it right after this. S Y L Y S K S K.

All right. So, uh I don't need to go over what we've been talking about because everyone's listening. So, at this point, um, the record labels that were handling this kind of music, it it wasn't like the major label stuff at at at this time, like that would happen in the future. Um, but it was it was basically hip-hop labels. You had Bad Boy with Shawn Combmes, uh, Death Row Records on the other side. Um, 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, uh, Marian Suge Knight. uh spelled s u g- e.

Uh he was the CEO of Death Row Records. Yeah. And he was a blood like he was, you know, he was a straightup blood from from South Central Los Angeles.

Yeah. Um 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 the CEO of the record label is a blood. Not a former blood, a blood.

Yeah. So, we talked about how the Quad um studio shooting like really kind of started the beef. 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 Suge Knight, who'd been visiting Tupac in jail and apparently had bought into Tupac's theory that um Shan Combmes and Biggie Smalls had set him up to be shot and robbed. Um, Suge Knight was accepting an award and during his speech, he invited any any um 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 Combmes.

Yeah. He said, "Come on over to Death Row Records." And I mean, if you go back and look at like Biggie Smalls um videos and like basically any rapper on this label at the time,

oh yeah, Sean Combmes is probably going to pop up making a cameo if not dance on it usually with his shirt wide open.

He 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 Shawn Combmes at a the Source Awards.

Yeah. 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.

Yeah. I mean, I remember at the time thinking cuz uh I 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 Combmes was always in those videos just like like you said either dancing or just like Yeah. Yeah. in the background.

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. Uh cuz he wasn't I guess you know he was a like you said an executive and a producer and uh I was I remember thinking that 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. Um, that when you compared them to them, he became even even more cringey, right?

Yeah. Yeah, for sure 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 um Shawn Combmes. Sean Pump 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. Uh cuz Chuck D like dead in the bullseye for me. Oh, yeah. Oh, yeah. 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 um instrumental track to a lot of their stuff.

It's too hard, raw, edgy for me. Yeah, I liked it. I mean, trust me, I was way more into like uh the Tribe Called Quest and Far Side and uh Jungle Brothers and like that kind of style. Uh, so Public Enemy, me being into Public Enemy in high school is definitely kind of a weird thing.

Yeah, but as I was listening to The Smiths in the Cure. That's right. No, I'm with you. I was listening to Smiths in the Cure, but also like Boot Camp Click, like Smith and Wesson, Nas, Wuang, Gangstar.

Yeah. See, I never I like Gangstar, but I never got into Wuang. They were pretty good. They were They were better solo. I think most of like Method Man and Rizza were better solo than Muang together, but whatever.

And this is two middle-aged white guys discuss their hip-hop past. I know. I do have to say that Dr. Dre's the Chronic was literally lifechanging.

Oh, for sure. And I 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 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 um Doggy Style Snoop's debut solo album. It's not It does not hold up.

Yeah. I mean, it's not It wasn't as good as The Chronic by a mile, but I liked it as much as The Chronic at the time, and I don't anymore.

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.

Man, he's amazing. He's now the owner of Death 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 Pton 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 was an Olympic mascot along with Flavor Flave.

Now I'm picturing uh Snoop Dogg, Pedro Pascal, and Pton Manning and just sitting at at lunch just saying like, "Guys, isn't this great?" I could see that. Talking about um mutual funds.

Yeah, we should do something together because we're not out there enough, right? It'll blow everyone's mind.

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

Yeah. Uh a fight breaks out and uh a guy named Jake Robels, it was a death row employee and he was a blood uh and a close friend of Suge Knight. He was shot and killed and witnesses were like Sean Colmes's bodyguard is the one who did it,

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

So, uh, at this time, uh, Death Row is at Can-Am Studios outside LA. That's what they're working out of. And uh people, you know, at the time were like, you know, the the real stuff is going down there. There's a big gangster culture in and around that studio. Um Suge Knight is is a a real heavy. He's 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 uh with 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. Uh, but all of this is sort of happening around Can Studios,

right? Um, so Tupac gets out of prison and remember like this guy's like a essentially a heat-seeking missile focused on Biggie Smalls. Like I'm 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 um popular recording artist at the time. He offered her $25,000 to be on one of um his records, a track for his um album, All Eyes on Me. And she did. She's like, "Sure, 25 grand. I'll do it." Um, and I guess after she performed or laid down the track, I guess as it's called, um, he was like, I 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 uh 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 um questions, you know, that in his head.

Yeah. And this is his wife, so like it's on for real at this point. Uh there's no coming back. Uh at the Soul Train Award show, this was in March of 96. Uh Tupac and Biggie both won awards, so they were there. Uh that was the first time they had been together since that quad studio shooting. Uh which is where it all started. And they both had their guys with them. They both had their entouragees. Uh Tupac had the Bloods. Uh Biggie had the Southside Crips on his side.

Uh and there was a guy named uh Keith D and he was a Uh so he was with um Biggie. And outside of this um at the Soul Train Award show,

uh they got into a fight basically. Uh witnesses said that Tupac is shouting shouting down Biggiey's groups, sort of inciting them. Uh they all brandish guns. Uh 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. Um, so Tupac released Hitim Up, which is considered one of the best diss tracks of all time. He actually specifically names Biggie by well by name. He also um talks about how he slept with Biggiey's wife, Faith Evans.

Yeah. Um, 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 um 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. Um it also helped sell magazines. Uh there's a Vibe magazine from September 1995 and on the cover is um Biggie Smalls and Sean Combmes and it talks about east versus west. Some people put their finger on that vibe uh issue and and point to it as like fanning the flames of this beef um and essentially making these these two um groups like have to hate each other even more or else they're going to seem weak or like you know um fake whatever.

Yeah, for sure. Uh and while this is all going on, Tupac is becoming a little more paranoid um about Death Row Records. Um, and Suge Knight and basically like Suge 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 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 uh on September 7th, 1996.

Uh, a lot of people connected with Death Row Records. uh Tupac, you know, as one of them went to the Mike Tyson fight against Bruce Seldon in Las Vegas. And after the fight, uh one of the Death Row group members, he was a blood named uh Travon Lane, saw a guy who said, "Hey, he stole a Death Row necklace from me a few months ago." Uh that guy's name was Orlando Anderson. He was a

and a nephew of Keith D. and uh Tupac, Suge Knight, and other people uh jump Anderson uh rough him up pretty good. And a few hours later, uh Sug Knight and Tupac are at a stoplight. Uh Cadillac pulls up next to them and the car is shot up and Tupac uh is dead 6 days later at the age of 25.

Yeah. Apparently, he was like making jokes and everything as he was being put onto the gurnie 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 Combmes." They had they said they had nothing to do with it. Um, but this this this did kind of give um Biggie Smalls like a 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 seems 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 driveby. You know, that seems like almost certainly the explanation for the whole thing.

Yeah. I mean, that's who the cops uh thought from the very beginning. Uh, it was the guy that was jumped and beat up. Um, they didn't arrest him. He died a couple of years later in a shooting in Compton. Uh, fast forward all the way to 2019 in a memoir where Kee D admitted that he was in that Cadillac. Uh, he said, "I gave the gun to Anderson. He was in the back seat. There were two other guys in the car. Uh, some people say it was a guy named DeAndre Smith who was the actual trigger man." Uh, 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. Uh after all these allegations and revelations about what um Shawn Combmes has been up to came out, they've come forward and been like, "We 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 is gone now. Like you said, age 25. Um, and if you want, you can go. You know where Clarkston is, Chuck?

Uh, sure. That was a rival high school of Reedan. 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 and 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. It's strange, but it's cool.

That 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 somewhere. I'll go check it out.

So So I think what, Chuck? Like um less than six months. No, right at about six months after Tupac was killed, uh Biggie Smalls was murdered. Yeah, this was uh March 1997. Uh he was in a car, riding in a car, leaving a 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 Big E's murder

in retaliation for um Tupac shooting." Right. Yeah. It's also entirely possible that Shawn Combmes did this, too. But it 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. Um Shawn Combmes car ran a red light and Biggie's car stopped at it. So Shawn Combmes wasn't near the shooting when it happened. Um there was a FBI agent who came forward or actually I guess created a whole um report on this who was like it this it was essentially the LAPD hiring a hitman at the behest of either Suge Knight or Shan Combmes. And it so it was not Tupac's probably was not a conspiracy. Biggie Smalls murder was almost certainly a conspiracy.

Yeah. And you know, Sug Knight would have done all this from jail. He was in jail at the time. Uh he is in jail. He's in prison now. Again, uh this is from this is a 28-year sentence. So this 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. Uh but Biggiey's last record or last, you know, sort of official release. I know they both put out a lot of stuff postumously. Uh but the his next like real uh drop was Life After Death was called that before he was murdered. Uh but that sold more than 10 million copies and certified diamond.

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

Yeah. Um, did you know Suge Knight has a podcast from jail called Collect Call?

Uh, it's not, but that's a pretty good name for podcast from prison. Agreed. Yeah.

Um, do 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. Um, rap became more decentralized and groups like Outcast came around and the the whether they 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. Cuz people are like, "No one's got a beef with Big Boy and Andre." No, everybody loves them for sure. Like I I know we sound maybe facitious. We are not being facitious right now.

No. Boy, I'm a 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 Rashida or another one. Another one. Not Rashida. I don't think it was Rashida. I don't know.

I wonder I wonder how I wonder how that fight went. It's a widespread rumor. And apparently also um 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.

Oh wow. And apparently in addition to beating him up and everyone said no one cares which side you're on Michael Jackson.

You don't have that kind of cred. No. Yeah. But it is a like Big 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. Um Chuck said, "Yeah, that means it's time for listener mail." Yeah, this is just uh 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.

Uh my mom put me on to you guys and I basically never stopped. So, thanks mom. Thanks, Mom.

Uh I've been binge listening recently. I do that every so often and 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. Indeed.

Keep up the good work, fellas. And that is Josiah B. And Josiah had a lot of good ideas, including uh Anne Frank, Oscar Schindler.

Uh Mottown. Okay. I want to do Mottown for sure. Uh 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' you think? Did you see it? No.

Uh it was okay. uh and the Hindenburg and that uh the 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, uh I definitely know we're going to get to that one.

Okay. Booya. Who was that 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. Uh, if you want to be like Josiah and email in, we would love to hear from you. You can send it off to stuffodcast at iheartradio.com.

Stuff You Should Know is a production of iHeart Radio. For more podcasts, iHeart Radio, visit the iHeart Radio app, Apple Podcasts, or wherever you listen to your favorite shows.

Questions about this episode

Who speaks in "The Ballad of Biggie and Tupac | STUFF YOU SHOULD KNOW"?

Josh Clark (Host), Chuck Bryant (Host), Jerry (Guest).

What is "The Ballad of Biggie and Tupac | STUFF YOU SHOULD KNOW" about?

The discussion explores the notorious rivalry between hip-hop legends Biggie Smalls and Tupac Shakur, delving into their lives marked by violence, crime, and tragedy. The episode addresses the complexities of their relationship and the broader implications of their impact on the hip-hop culture of the 1990s, while also issuing a content warning for mature themes.

What is mentioned in this Stuff You Should Know episode?

34 people, works and ideas are mentioned, including Biggie Smalls, Hip-Hop, Tupac Shakur, Death Row Records, Shan Diddy Combmes, Suge Knight. Each one on this page links to its own page with every episode that mentions it.

How long is "The Ballad of Biggie and Tupac | STUFF YOU SHOULD KNOW"?

The episode runs 51 min; the transcript is about 9,649 words in 175 timestamped sections.

More from Stuff You Should Know

About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated January 24, 2026.