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January 22, 2026 51 mins

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.

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Speaker 1 (00:00):
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you and we can't wait to be back.

Speaker 2 (00:38):
Welcome to stuff you should know, our production of iHeartRadio.

Speaker 1 (00:48):
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 door anytime
I say hip hop, so I usually say rap. Yeah,
but regardless, that's what we're talking.

Speaker 2 (01:06):
About Yeah, we're talking about Biggie and Tupac, and we
want to issue a.

Speaker 3 (01:12):
Warning and a trigger warning.

Speaker 2 (01:14):
No pun intended there, but this one's obviously gonna because
we're talking about the lives 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,

(01:35):
and so you 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.

Speaker 1 (01:43):
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 nineties, you probably know that Biggie and Tupac had
probably the biggest rivalry in the hip hop world. It's
referred to as a beef between one another, so much

(02:06):
so that it actually triggered, or caused, at the very
least popularized the East Coast versus West Coast thing of
rap in the nineteen nineties. That was huge. It was
the central focus of rap during basically that whole decade.

Speaker 2 (02:23):
Yeah, and sadly would leave both of them dead from violence.
It was I hope that's not a spoiler for anyone,
but yeah, at very young ages. It's super sad what
happened to those guys, and just super sad that that was,
you know, brought about because of just sort of the

(02:44):
lifestyle that went along with their careers, you know.

Speaker 1 (02:47):
Yeah, And a lot of people make a case that
that lifestyle was essentially demanded by fans and the media
and certainly fostered and nurtured by fans in the media.
And so I think both Biggie and Tupac and all
the people around them and other rappers basically felt like
they had to act like they the stuff that they

(03:09):
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.

Speaker 3 (03:26):
Yeah.

Speaker 2 (03:27):
I mean, I think hip hop more than other types
of music too, there's an expectation to be.

Speaker 3 (03:34):
To be real again, got all these funs flying out of.

Speaker 1 (03:38):
My mouth, oh from Cypress Hill.

Speaker 3 (03:41):
Yeah, of course.

Speaker 2 (03:42):
But to be real and like you said, not you know,
if you were found out to be sort of rapping
about something and really kind of fake in real life
like that, that's no good for your career as a
hip hop artist. So it's sort of you know, they
I don't know, to me, they're sort of victims of
that whole thing in a lot of ways.

Speaker 1 (04:03):
Yeah, but at the same time, they definitely bought into it. 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.

Speaker 2 (04:20):
Yeah, So we're going to tell you a little bit
about Tupac and his beginnings, a little bit about Biggie
and then once they met up kind of what happened
from there. But as far as Tupac goes, he was
born in nineteen seventy one, same year as me. He
was born in Harlem. His mother was a Finny Shakur
and she was one of the Panther twenty one. I'm
pretty sure we talked about them in the Black Panther episode,

(04:43):
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 Lesaine Crooks.

(05:07):
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 the second, So
he's essentially he was always Tupac.

Speaker 1 (05:22):
Yeah, he was named after an eighteenth century Incon 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.

(05:43):
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 eighties in particular, did to make money

(06:06):
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.

Speaker 2 (06:15):
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, Leela Steinberg, was like, hey, I see

(06:37):
a lot of potential in you. You can crash on
my couch when you need to, And she ended up
becoming his first manager.

Speaker 1 (06:44):
Yeah, and she said, you always have to wear that
bandana around your head just so like you because I
love it.

Speaker 3 (06:50):
It looks super cool.

Speaker 1 (06:52):
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. 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

(07:15):
Humpty Hump was rapping about how big his nose was
and having sex and burger king bathrooms, right like Tupac
was rapping about what poverty and crime are like in
the black community.

Speaker 3 (07:26):
You know, he didn't go by Humpty Hump.

Speaker 1 (07:29):
What was this? Why do You Go Buy?

Speaker 3 (07:30):
That was shock G.

Speaker 1 (07:33):
I've heard him referred to on other songs as.

Speaker 2 (07:35):
Well, all right, aka Humpty Hump. So yeah, you weren't
completely wrong.

Speaker 1 (07:41):
A little side. I would direct people to the mrs
song Risky Business that features 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 Tupac Ellipse. Now, there was no other title that

(08:03):
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.

Speaker 3 (08:23):
Yeah, for sure.

Speaker 2 (08:25):
Dan Quayle kind of gave him a little more press
when 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 mm hm. And
he started acting kind of right afterward. In nineteen ninety
two and nineteen ninety three, he put out where he
was in the movies Juice and Poetic Justice, both really

(08:45):
great movies. Juice is awesome, actually, so is Poetic Justice.
I love both of those movies.

Speaker 1 (08:50):
The one I've seen him and I don't think. I
think I saw Juice. I didn't see Poetic Justice. I
saw Above the Rim. He was really good, and Above
the Rim.

Speaker 3 (08:57):
I never saw that one.

Speaker 1 (08:58):
Oh that's a good one. He should see it.

Speaker 3 (09:01):
Wet them together and have a Tupac watch party.

Speaker 1 (09:03):
I guess, Okay, let's do that.

Speaker 3 (09:05):
Yeah.

Speaker 2 (09:06):
But he started getting a little more famous, sort of slowly,
and this is when kind of the early nineties, 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.

Speaker 1 (09:23):
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.

Speaker 3 (09:35):
Yeah.

Speaker 1 (09:36):
He shot at off duty police in Atlanta in nineteen
ninety three when he tried to prevent them from 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,

(10:02):
that just formed, melded really quickly right out of the gate,
Like this guy was legit as far as his fans
were concerned.

Speaker 3 (10:11):
Yeah, for sure. So that's Tupac's early days.

Speaker 2 (10:14):
Biggie Smalls was born he's a little younger. He's born
in nineteen seventy two 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, Veletta, really thought a

(10:36):
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 in Tech Education High School,
which had quite an alumni base as far as hip
hop goes, because DMX, Buster Rhymes, Love Busta, and jay
Z all went there.

Speaker 1 (10:57):
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.

Speaker 2 (11:03):
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.

Speaker 3 (11:21):
With my eyeballs.

Speaker 2 (11:22):
Really, he's astoundingly good looking, and I wanted to go
over and say, like, hey man, we grew up in
the same neighborhood basically.

Speaker 1 (11:30):
And you're really good looking, You're really handsome.

Speaker 2 (11:33):
But he I'm such a big fan of his but
from his music to his acting. But he was with
his family and like it was just like, I'm just
not going to do that.

Speaker 1 (11:41):
Instead, you got in your car and shouted Dan high
rules and like laid rubber peeling out of the parking lot.

Speaker 3 (11:48):
Yeah that's right. Sure, Danger Mouse went to my high
school too, though.

Speaker 1 (11:52):
Oh yeah, oh I forgot about Danger Mouse. Danger Mouse
did that gray album with the Beatles, and.

Speaker 3 (12:00):
Right, I don't know, we'll.

Speaker 1 (12:04):
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 and high school. But also like Tupac, his
family was not exactly well to do. Remember, his mom

(12:26):
took a second job to put him just through high school.
So he started selling drugs on the side, crack again
because it's the eighties, 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.

Speaker 2 (12:48):
Yeah, he ended up in jail, actually spent nine months
in jail at one point because it 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 nineteen seventy five 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

(13:10):
of did it for fun, and that got him on
Source magazine's list in nineteen ninety two of Unsigned in
their Unsigned hype Columneah, which eventually put him on a
compilation with other Unsigned rappers, which eventually landed him on
the ears of a twenty.

Speaker 3 (13:27):
Three year old named named Sean Combs.

Speaker 1 (13:30):
So yeah, Shawn Combs, puff Daddy did he People have
probably heard of him by now for all sorts of reasons.
His career as a twenty three 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

(13:54):
as bad Boy Records, and one of the first things
he did was sign Biggie Small's 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.

Speaker 2 (14:11):
Yeah and his when he put out his first single,
it was under the name Notorious Big because of legal issues.

Speaker 3 (14:18):
I guess with the movie Yeah Biggie Smalls was that
my take you? Okay? So he was Notorious Big Ig
officially everyone called him Biggie. Of course.

Speaker 2 (14:27):
He had as a kid in ninety three with his
high school girlfriend jan Jackson, not Jana Jackson, and he
hadn't really broken through at this point, even though he
was with Shawn Combs at the time. But he you know,
so he continued to kind of deal drugs, apparently colms.
It was like, he can't do that kind of stuff
if you want to get anywhere.

Speaker 3 (14:48):
But he broke up with his.

Speaker 2 (14:51):
High school sweetheart who he had his first kid with
and a few months after that ended up with Faith Evans.

Speaker 3 (14:57):
Who was also on the Bad Boy label.

Speaker 2 (14:59):
And that is is Biggie and his start, So good
time for a break.

Speaker 1 (15:04):
Yeah, we're at nineteen ninety three, Tupac's already a star
and Biggie's starting to come up.

Speaker 3 (15:09):
All right, We'll be right back.

Speaker 1 (15:10):
As why why Why s K as big.

Speaker 4 (15:17):
Tough. He should know, definitely should know, Charles s K. So.

Speaker 1 (15:34):
One of the things you may or may not know,
if you're just kind of passing 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 pretty well known
around New York, and Tupac kind of became a mentor

(15:58):
to him. They met in nineteen ninety three, and they
hung out with a bunch of other people, played around
with a bunch of guns at Tupac's house, and they
became close enough that whenever Biggie went out to la
he stayed on Tupac's couch.

Speaker 3 (16:14):
That's right.

Speaker 2 (16:14):
Uh, 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,
it was called Ready to Die in nineteen ninety four,
and before that, Biggie was like, you know what, I
think you should just be my manager and take over
from takeover for Shawn Combs, and Tupac was like, no, man,

(16:38):
you need to stick with that guy. Apparently Tupac wasn't
a big fan of Combs. Yeah, but you know he
said that I had a feeling he just didn't want
to get into managing him.

Speaker 1 (16:49):
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 the thing 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
Seawn Combs again remember inextricably linked BFF with Biggie as

(17:14):
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 Bickie got to be friends with Tupac.
The reason Tupac didn't care about being friends with Sean
Combs is that he thought Shawn Combs was basically a poser.
He was a record executive, playing like he was a

(17:36):
hardcore rapper, and he didn't have much respect for him.
And I think that really kind of came through to
Shawn Combs after a little while, and he didn't he
started not liking Tupac.

Speaker 3 (17:48):
Yeah, that's right.

Speaker 2 (17:50):
So the beef is sort of the beef seed is
planted as they are, you know that old saying.

Speaker 1 (17:56):
Where's the beef seed?

Speaker 2 (17:57):
It's been exactly red to die. Like I mentioned, was
Biggie's debut in ninety four. It was a big hit
that 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

(18:18):
of New York right off the bat. And it's a
great record, he was you know, he rapped a lot
about you know, sort of like the lifestyle and the
gangs of stuff that he was doing. But also there
was a lot of vulnerability on that first record too.

Speaker 1 (18:32):
Yeah. Yeah, he and Tupac wasn't shy about rapping about
mental health and stuff like that. And up to this point,
like you did not talk about that kind of stuff.
It was all about partying and having sex and like
doing drugs and all that stuff. You didn't talk about
being paranoid or like super worried about being killed or
anything like that. And I just to kind of set

(18:52):
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 Rick and ll cool J and all
them the ones who were coming up in the eighties.

(19:13):
At the time that Biggie Small's record came out, everyone
was all about Doctor dre Ice Cube, Snoop Dogg, 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

(19:34):
a rapper of the caliber of Biggie Smalls to do
something like that, because there are tons of other albums
that had come out, like Tribe Called Quest had three
albums by this time, and yet the Biggie Small's record
coming out just completely undid essentially caused an earthquake in
the rap world and tilted everything back to New York.

Speaker 3 (19:56):
Yeah, for sure.

Speaker 2 (19:58):
So as this is happening and Biggie's blowing up like
in a big way, Tupac is in New York filming
a movie in nineteen ninety three 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.

Speaker 3 (20:16):
Tupac likes this guy. They start partying together.

Speaker 2 (20:20):
Biggie knows about Haitian Jack because he was pretty familiar
with the street gangs of New York, and he warns
his friend Tupac and he's like, man, this guy is
real trouble. So like you 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.

Speaker 1 (20:42):
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 Ayana Jack. She was nineteen at the time, while
he was in New York filming hanging out with Haitian Jack,

(21:05):
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

(21:26):
is Tupac is now charged with sexual abus, 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

(21:48):
gang rape charge.

Speaker 2 (21:51):
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 misdemeanors and avoided jail time. Tupac
always said he was innocent and that he was set
up and sold out by Haitian Jack. But that, you know,
we need to point out that completely contradicts the story

(22:13):
of the victim from Ayana 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.

Speaker 1 (22:28):
Yeah, and the thing that really kind of blew this
this whole thing up is Tupac said as much. He said,
Haitian Jack cooperated with the police, This major actual gangster
in New York cooperated with the police. In an interview
with the New York Daily News, So the New York
Daily News prints Tupac saying that, and that did not
make Haitian Jack very happy. Those two separated immediately. They

(22:51):
didn't talk anymore. They weren't friends anymore, they didn't hang out,
and no, Tupac had essentially an enemy in Haitian Jack,
which is from what I can tell, not what you
want it.

Speaker 3 (23:01):
No, not at all. So the case is moving forward.

Speaker 2 (23:04):
At this point, Tupac is financially strapped because while he
is making money, he's spending it faster than he's making it.
He's also helping out friends and family with their finances.
So there was an invitation from a guy named Jimmy
Henchman Roseman. He knew Shawn Combs, he knew Haitian Jack,
and he said, Hey, Tupac, why don't you do a

(23:26):
guest spot for this rapper, Little Sean. He's in Biggie Circle.
He's a guy with Shawn 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 thirtieth along with three of his guys, and
before getting on the elevator to go up and record,

(23:49):
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, ends
up being robbed, He ends up being beaten pretty badly.
And Combs and Biggie and Henchman Jimmy Henchman Roseman were

(24:09):
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.

Speaker 1 (24:27):
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. He didn't warn him.
There's no evidence whatsoever either one of those things happened. Yeah,
And Biggie Small's always is like, no, I like this

(24:50):
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.
He's 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

(25:10):
great that Blood's hung out with one side, I think
Tupac 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 crush things up. That is not going to
happen with you now hanging around with the Crips and

(25:32):
the Bloods.

Speaker 2 (25:33):
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.

Speaker 3 (25:40):
This and that.

Speaker 2 (25:41):
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 has found guilty of
sexual assault, he's acquitted on the other charges, and he
sent its to eighteen months in prison and where his

(26:01):
third album came out, Me Against the World, came out
while he was in prison serving that sentence.

Speaker 1 (26:06):
Dude, if you want cred, release your rap album while
you're in prison.

Speaker 3 (26:12):
Yeah, called Me against the World.

Speaker 1 (26:14):
Yeah exactly.

Speaker 3 (26:15):
Yeah.

Speaker 1 (26:16):
So, while Tupac was in jail, I don't remember how
long he was in for it, eighteen eighteen months, Okay.
While he was in jail, Biggie releases a track called
who Shatcha, and Tupac interprets that as it was completely
directed to him. It was essentially Biggie Small's gloating about

(26:37):
having set up Tupac, and now Tupac was in jail
and he'd been shot, and that seems to not be
the case at all. Biggie Smalls apparently wrote that song
before the Quad City shooting. And again, just from all evidence,
it seems like Biggie had no problem with Tupac. This
is all in Tupac's head. Like this whole East Coast

(26:57):
West West Coast beef seems to have come from Tupac
being paranoid, essentially, And I looked up why he might
have been paranoid, and apparently there's pretty widespread acknowledgment or
belief that he was suffering from substantial mental health issues
while he was alive, and that that had a huge

(27:19):
impact on the way that he interacted with people, the
level of trust he would afford, even the closest people,
Like I think it was very easy to fall out
of his favor because you might do or say something
that he suddenly found suspicious and now all of a sudden,
like you were his enemy, like you would do something
like set him up or rob him or pay for
him to be killed or something.

Speaker 3 (27:39):
Yeah, I wondered about that. I'm glad you looked into that.

Speaker 1 (27:42):
Thank you, I am too.

Speaker 3 (27:43):
You're welcome. Maybe we should take another break.

Speaker 2 (27:47):
Yeah, all right, we'll take another break and we'll we'll
get back to it right after this.

Speaker 1 (27:51):
As why why.

Speaker 4 (27:53):
SK as good.

Speaker 2 (27:58):
Tough?

Speaker 4 (27:58):
He should know?

Speaker 1 (28:03):
Definitely large house of h.

Speaker 4 (28:11):
Y s K.

Speaker 2 (28:14):
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, 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.

Speaker 3 (28:32):
It was basically hip hop labels.

Speaker 2 (28:34):
You had bad Boy with Shawn Comb's death Row Records
on the other side, that company was founded about the
same time in nineteen ninety two by Doctor Dre and
a few other guys, and one of those guys was
his former bodyguard, Marion sug Knight.

Speaker 3 (28:49):
Spelled s u g e h.

Speaker 2 (28:52):
He was the CEO of death Row Records and he
was a blood like he was you know, he was
just a straight up blood for from South central Los Angeles.

Speaker 1 (29:02):
Yeah, 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
form of blood, a blood.

Speaker 3 (29:22):
Yeah.

Speaker 1 (29:22):
So we talked about how the Quad Studio shooting like
really kind of started the beef. The thing that made
that beef really genuinely public came at the award show
for Source Magazine their annual awards this time this one
was in nineteen ninety five, where sug Knight, who'd been
visiting Tupac and Jail and apparently had bought into Tupac's

(29:43):
theory that Seawn Combs and Biggie Smalls had set him
up to be shot and robbed. Suge Knight was accepting
an award and during his speech he invited any rapper
who didn't want to worry about the executive producer trying
to be in all the videos, which was a direct
shot at Shawn Comb's. He said, come on over to

(30:06):
death Row Records. And I mean, if you go back
and look at like Biggie Small's videos and like basically
any rapper on this label at the time, oh yeah,
Shawn Combs is probably going to pop up making a cameo,
if not dance on it, usually with his shirt wide open.
He really was not. He was not what they, like

(30:28):
death Row Records was doing. And so, like Suge 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 Sewan Comb's at the Source Awards while you're accepting
an award. It was a big deal. That really kind
of made that beef public and it turned into East

(30:51):
Coast versus West Coast essentially immediately.

Speaker 2 (30:53):
Yeah, I mean I remember at the time thinking because
I remember just and it wasn't just rappers like they
had like some R and B acts And I feel like,
I feel like Combs was always in those videos just
like like you said, either dancing or just like yeah
yeah in the background.

Speaker 1 (31:12):
Yeah.

Speaker 2 (31:12):
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 call quests and that kind of thing,
and you know, Doctor Dray and Snoop. I was into
that at first, but this generally wasn't my thing. But
I remember thinking, like, this guy's like he sucks, like
he's not he's not a talented artist, no, because he wasn't.

Speaker 3 (31:34):
I guess you know.

Speaker 2 (31:35):
He was a like you 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?

Speaker 1 (31:42):
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 cringey.

Speaker 3 (32:04):
Right, Yeah, yeah, for sure he was.

Speaker 1 (32:06):
It 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. Seawan Combs just kind of had him
under his thumb.

Speaker 3 (32:21):
Yeah, absolutely, which is sad.

Speaker 1 (32:22):
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.

Speaker 3 (32:34):
What about you as the greatest rapper of all time?

Speaker 1 (32:37):
Well, it's between Tupac and Biggie how about that?

Speaker 3 (32:40):
Oh okay?

Speaker 2 (32:41):
Because 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.

Speaker 1 (32:48):
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 edgy
for me.

Speaker 2 (33:01):
Yeah, I liked it, I mean, trust me, I was
way more into like, uh, the tribe called Quest and
Far Side and 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.

Speaker 3 (33:20):
Yeah, But as I was listening to the Smiths and
The Cure, It's.

Speaker 1 (33:23):
Right, no, I'm with you. I was listening to Smith's
and The Cure, but also like boot Camp Click, like
Smith and Wesson, Nah's Wu Tang Gangs.

Speaker 3 (33:31):
Yeah, I see. I never I like Gangstar, but I
never got into Wu Tang.

Speaker 1 (33:35):
They were pretty good. They were they were better solo.
I think most of like method Man and Rizza were
better solo than Wu Tang together.

Speaker 3 (33:42):
But whatever, and this is two middle aged white guys
that's their hip hop pass.

Speaker 1 (33:47):
I do have to say that Doctor Dre's The Chronic
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 trajection.

Speaker 3 (33:58):
I was one of them.

Speaker 2 (33:59):
Man, that thing by heart and inside and out. It's
a fun listen when I put it on a lot
of nostalgia, Let's back it is.

Speaker 1 (34:06):
I thought the same thing would be for Doggie Style
Snoop's debut solo album, It's not It does not hold up.

Speaker 4 (34:15):
Yeah.

Speaker 3 (34:15):
I mean it's not like it wasn't as good as
the Chronic, not a mile.

Speaker 1 (34:19):
But I liked it as much as the Chronic at
the time, and I don't anymore.

Speaker 3 (34:23):
Yeah, I'm with you.

Speaker 2 (34:24):
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.

Speaker 1 (34:29):
Man, he's amazing. He's now the owner of the Thrower Records.

Speaker 2 (34:33):
No, he's awesome, but I just feel like he's he's
a bit over exposed for my taste.

Speaker 1 (34:38):
Oh, I see, he's like the the Peyton Manning of
the hip hop world. He's the Pedro Pascal of rap.

Speaker 3 (34:46):
Okay, even better said, but he's.

Speaker 1 (34:47):
An American treasure though. I mean like he's an Olympic
mascot along with Flavor Flav.

Speaker 2 (34:53):
Now I'm picturing Snoop Dogg, Pedro Pascal, and Peyton Manning
and just sitting at lunch just saying, like, guys, this
is great.

Speaker 1 (35:01):
I could see that talking about mutual funds.

Speaker 3 (35:04):
Yeah, we should do something together because we're done out there.

Speaker 1 (35:07):
Enough, right, it'll blow everyone's mind.

Speaker 3 (35:11):
All right.

Speaker 2 (35:12):
So we are in September nineteen ninety five, At this point,
sug Knight has dropped the dropped the bomb at the
Source Awards, which I'm sure did not sit well with
Shawn Combs. And Tupac is in prison at this point,
and Knight and Comb's go to the same party here
in Atlanta at what was called the Platinum House. It's

(35:33):
a strip bar over on Piedmont Road near the Colonnade.

Speaker 3 (35:37):
Which you love.

Speaker 2 (35:38):
Yeah, a fight breaks out and a guy named Jake
Roebles it was a death Row employee and he was
a blood and a close friend of sug Knight. He
was shot and killed and witnesses were like, Seawan Combs's
bodyguard is the one who did.

Speaker 1 (35:54):
It, right, So this is not good. This has not
helped this rivalry at all. And eventually, I guess over
the same time, Tupac is still in prison, but sug
Knight is still visiting Tupac there, and like they're becoming
closer and closer because not only is Suge Night going
out of his way to go visit Tupac in prison,

(36:14):
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 sug Knight,
but apparently they have become real friends. He releases his
fourth album, All Eyes on Me. I think it was
in February of nineteen ninety six, like immediately when double Platinum.

(36:38):
I think it went to number one on the charts.

Speaker 2 (36:41):
So at this time, Death Row is at CANAM Studios
outside La That's what they're working out of, and people,
you know at the time were like, you know, the
real stuff is going down. There's a big gangster culture
in and around that studio. Sug Knight is a real heavy.

(37:02):
He's threatening people right and left if they don't, you know,
aren't on his good side. And people are hanging out
there with gang members who are their security. So there's
you know, there might be bloods there one day, there
might be crips there one day. There might be a
huge singer there one day recording. But all of this
is sort of happening around can M Studios.

Speaker 1 (37:23):
Right. So twopuckets out of prison, and remember like this
guy's like essentially a heat seeking missile focused on Biggie Smalls.
Like I get the impression that he just sat in
prison like ruminating about Biggie Smalls and getting back at him.
So one of the first things he does was hire
Biggie Small's wife, Faith Evans, who was herself a pretty

(37:45):
popular recording artist at the time. He offered her twenty
five thousand dollars to be on one of his records,
a track for his album All Eyes on Me, and
she did. She's like, sure, twenty five grand I'll do it.
And I guess after she performed or laid down the track,
I guess what it's called. He was like, I got

(38:08):
my check at the hotel room. You got to come
over to my hotel room to get it.

Speaker 3 (38:11):
The red flag.

Speaker 1 (38:12):
Yeah, so she went. Both of them say that he
propositioned her. He says that they had sex. She has
repeatedly denied and emphatically denied that they did. But just
the fact that they were in a hotel room together
gave tupac even if it wasn't true that they had sex,
gave him plenty of grounds to tell everybody that they
did have sex to at least gnaw at Biggie Small's

(38:36):
with questions, you know in this yeah.

Speaker 2 (38:39):
Yeah, and this is his wife, so like it's on
for real. At this point, There's no coming back. At
the Sole Train Award show, this in March of ninety six,
Tupac and Biggie both won award, so they were there.
That was the first time they had been together since
that Quad Studio shooting, which is where it all started.

Speaker 3 (38:57):
And they both had their guys with them. They both
had their entourages.

Speaker 2 (39:00):
Tupac had the Bloods, Biggie had the South Side Crips
on his side, and there was a guy named Keith
d and he was a crip, so he is with Biggie.
And outside of this, at the Soul Train Award show,
they got into a fight.

Speaker 3 (39:16):
Basically.

Speaker 2 (39:18):
Witnesses said that Tupac is shouting, shouting down biggiees groups,
sort of inciting them. They all brandish guns, but nothing
happens at this point, just a lot of sort of
back and forth and like, you know, I've got my gun,
so shut up.

Speaker 1 (39:33):
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 Him Up, which is considered one
of the best diss tracks of all time. He actually
specifically names Biggie Bye Well by name He also talks
about how he slept with Biggie's wife, Faith Evans. Yeah,

(39:55):
and while this is also going on, there's like a
lot of money to that people have figured out we
can make from this, right, like this beef and like say,
you know, some street skirmishes or whatever. This stuff makes news, right, Like,
people know about this and this is before I think
cell phones were still kind of bricky at the time,

(40:17):
long before the Internet, like, 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 nineteen ninety five, and
on the covers Biggie Smalls and Sean Combs and it
talks about East versus West. Some people put their finger

(40:38):
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.

Speaker 2 (40:58):
Yeah, for sure, And while the this is all going on,
Tupac is becoming a little more paranoid about death Row
records and sug Knight and basically like suge Knight's kind
of controlling the money, saying that you know you're gonna
blow all your money unless I'm in control. He didn't
think he was getting the proper royalties. He thought, you're
holding me back in Hollywood, and I'm trying to get

(41:20):
my movie career going. So like trouble is sort of
brewing on the inside there, which finally would culminate. On
September seventh, nineteen ninety six, a lot of people connected
with death Row records, 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

(41:41):
Row group members, he was a blood named Trevon Lane,
saw a guy who said, hey, he stole a death
Row necklace from me a few months ago. That guy's
name was Orlando Anderson. He was a crip and a
nephew of Keith d and Tupac. Sug Knight and other
people jump Anderson rough him up pretty good and a

(42:03):
few hours later, Suge Knight and Tupac are at a
STOPLIGHTE Cadillac pulls up next to them and the car
is shot up in Tupac.

Speaker 3 (42:13):
Is dead six days later at the age of twenty five.

Speaker 1 (42:16):
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.

Speaker 3 (42:24):
Yeah.

Speaker 1 (42:25):
So a lot of people are like, this is Biggie,
this is Sean Combs. They had they said they had
nothing to do with it, but this, this, this did
kind of give Biggie Smalls like a wide opening to
be like, this stuff has to stop. These this East
coast West coast thing has gotten out of hand. And

(42:46):
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 drive by.
You know, that seems like almost certainly the explanation for
the whole thing.

Speaker 2 (43:02):
Yeah, I mean, that's who the cops thought from the
very beginning. It was the guy that was jumped and
beat up. They didn't arrest him. He died a couple
of years later in a shooting in Compton. Fast forward
all the way to twenty nineteen. 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

(43:22):
back seat. There were two other guys in the car.
Some people say it was a guy named DeAndre Smith
who was the actual trigger man. But basically everyone in
that car ended up being killed except for Keith D.
And in September twenty twenty three, he was arrested and
charged with Tupac's murder. And that trial is going to

(43:44):
happen all these years later, coming up this summer in
August of twenty twenty six.

Speaker 1 (43:49):
Yeah, and Keith D and later on a Bad Boy
co founder named Kirk Burrows and others. After all these
allegations in revelations about what Sean Combs has been up
to came out, They've come forward him and like we
think he actually did have something to do with this.
Seems like a pretty quick turnaround to me. I think
it was just crips retaliating for a beatdown. So Tupac

(44:13):
is gone now, like you said, age twenty five, and
if you want, you can go. You know where Clarkston is, Chuck?

Speaker 3 (44:21):
Uh? Sure? That was a rival high school of Ridan.

Speaker 1 (44:25):
There is a Tupac statue in memorial in Clarkston.

Speaker 3 (44:28):
Did you know that I did? I've never seen it though.

Speaker 1 (44:30):
We went there, You mean, I went there, and it's
pretty it's pretty amazing, and it's just in the middle
of this little RinkyDink suburb of Atlanta. Strange, but yeah cool.

Speaker 2 (44:40):
That was kind of my stomping grounds. Was that area
of Memorial Drive where Clarkston was z owned?

Speaker 1 (44:45):
Oh yeah, yeah, Well we'll have to go to the
Tupac statue together.

Speaker 3 (44:48):
I'll go check it out.

Speaker 1 (44:49):
So I think what Chuck like, less than six months no,
right at about six months after Tupac was killed, Biggie
Small's was murdered.

Speaker 2 (45:01):
Yeah, this was March nineteen ninety seven. He was in
a car, riding in a car leaving a party a
Vibe magazine in La pronounced dead at the hospital. He
was but twenty four years old. And immediately everyone was like,
this is Shuge Knight, who by the way, people blamed
Tupac shooting initially on Shuge Knight. Yeah, but he was

(45:22):
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. It definitely was in on
Biggie's murder.

Speaker 1 (45:31):
In retaliation for Tupac shooting, right. Yeah, It's also entirely
possible that Shawn Combs did this too, but it certainly
seems to have been a contract hit. Like the people
who killed Biggie Small's 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. Shawn

(45:53):
Comb's car ran a red light and Biggie's car stopped
at it. So Shawn 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 this. It was essentially the LAPD hiring

(46:13):
a hit man at the behest of either Suge Knight
or Sean Combs. And if so, it was not Tupac's
probably was not a conspiracy. Biggie Small's murder was almost
certainly a conspiracy.

Speaker 2 (46:27):
Yeah, and you know Suge Knight would have done all
this from jail. He was in jail at the time.
He is in jail. He's in prison now. Again, this
is from This is a twenty eight year sentence, so
this is a big one. And this is for the
death of a Compton businessman from twenty fifteen. He was
never charged in Biggie's killing. But Biggie's last record or

(46:48):
last you know, sort of official release. I know they
both put out a lot of stuff posthumously. But his
next like real drop was Life After Death. Was called
that before he was murdered. But that sold more than
ten million copies and certified diamond.

Speaker 1 (47:06):
Yeah, I guess not as Tupac released nine posthumous albums,
seven of them went platinum. Yeah. Did you know sug
Knight has a podcast from jail called collect Call uh Hit.

Speaker 3 (47:19):
That's a pretty good name. It's a great podcast from prison.

Speaker 1 (47:22):
Agreed. Yeah, you want to know what ended the East
Coast West Coast beef?

Speaker 3 (47:29):
Oh was that still not happening?

Speaker 1 (47:31):
No? No, it ended fairly soon after this rat became
more decentralized in groups like Outcast came out. Yeah, and
the whether you were from the East Coast or the
West Coast was watered down. It didn't matter nearly as much.
So you can thank Outcasts for ending the East Coast
West Coast rivalry.

Speaker 3 (47:49):
Yeah, because people are like, no one's got a beef
with Big Boy and Andre.

Speaker 1 (47:53):
No, everybody loves them for sure, Like I know we've
some maybe facetious. We are not being.

Speaker 3 (47:58):
Facetious right now. No, hell abotcast.

Speaker 1 (48:02):
One last thing. Apparently Michael Jackson assaulted Tupac once in
a studio when Tupac insulted Quincy Jones's daughter.

Speaker 3 (48:11):
Oh h, Rashida or another one.

Speaker 1 (48:15):
Another one, not Rashida. I don't think it was Rashida.
I don't know.

Speaker 3 (48:19):
I went. I wonder how. I wonder how that fight went.

Speaker 1 (48:23):
It's a widespread rumor. And apparently also, you know, Biggie
was on one of Michael Jackson's songs like doing his thing,
like legit doing his thing. It wasn't watered down for
the radio or anything like that. And apparently Michael Jackson
threw his lot in with Biggie and was not a
big fan of Tupac and snubbed him once. Oh wow,

(48:44):
and apparently in addition to beating him up.

Speaker 2 (48:46):
And everyone said, no one cares put side here on
Michael Jackson. You don't have that kind of cred.

Speaker 1 (48:53):
No, but it is a like Biggie does a pretty
good job on that song.

Speaker 3 (48:58):
I'll have to check it out.

Speaker 1 (49:00):
Okay, I think that's it, Chuck man.

Speaker 3 (49:02):
We did it.

Speaker 1 (49:03):
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 now.

Speaker 3 (49:15):
Yeah, this is just kind of a nice email with
some good suggestions. Hey guys, my name is Josiah Brown.
I live in Tennessee.

Speaker 2 (49:20):
I've been a devoted fan since I was about ten
years old and I'm twenty now. My mom put me
on you guys, and I basically never stopped.

Speaker 3 (49:27):
So thanks Mom.

Speaker 1 (49:28):
Thanks Mom.

Speaker 3 (49:29):
I've been binge listening recently. I do that every so often.

Speaker 2 (49:32):
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.

Speaker 3 (49:40):
Keep up the good workfellas, and that is Josiah Bee.
And Josiah had a lot.

Speaker 2 (49:44):
Of good ideas, including Ann Frank, Oscar Schindler. Motown Okay,
I want to do Motown for sure, mister Rogers, I
can't believe we haven't done that one yet.

Speaker 1 (49:56):
We were going to, and then that Tom Hanks movie
came out and kind of ruined it for a little while.

Speaker 3 (50:01):
Yeah, I finally saw that on a plane recently.

Speaker 1 (50:03):
Would you think did you see it?

Speaker 3 (50:06):
Uh? It was? Okay yep.

Speaker 2 (50:11):
And the Hindenburg, and that 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 I definitely know we're
going to get to that one.

Speaker 1 (50:22):
Okay, boo, Yeah, who is 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 will remember to credit you with them, right.

Speaker 3 (50:33):
That's right, except for the Hindenburg. Yeah, it's already in
the bad Okay.

Speaker 1 (50:37):
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 dot com.

Speaker 3 (50:48):
Stuff you Should Know is a production of iHeartRadio. For
more podcasts my heart Radio, visit the iHeartRadio app, Apple Podcasts,
or wherever you listen to your favorite shows.

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Two Guys, Five Rings: Matt, Bowen & The Olympics

Two Guys, Five Rings: Matt, Bowen & The Olympics

Two Guys (Bowen Yang and Matt Rogers). Five Rings (you know, from the Olympics logo). One essential podcast for the 2026 Milan-Cortina Winter Olympics. Bowen Yang (SNL, Wicked) and Matt Rogers (Palm Royale, No Good Deed) of Las Culturistas are back for a second season of Two Guys, Five Rings, a collaboration with NBC Sports and iHeartRadio. In this 15-episode event, Bowen and Matt discuss the top storylines, obsess over Italian culture, and find out what really goes on in the Olympic Village.

Milan Cortina Winter Olympics

Milan Cortina Winter Olympics

The 2026 Winter Olympics in Milan Cortina are here and have everyone talking. iHeartPodcasts is buzzing with content in honor of the XXV Winter Olympics We’re bringing you episodes from a variety of iHeartPodcast shows to help you keep up with the action. Follow Milan Cortina Winter Olympics so you don’t miss any coverage of the 2026 Winter Olympics, and if you like what you hear, be sure to follow each Podcast in the feed for more great content from iHeartPodcasts.

iHeartOlympics: The Latest

iHeartOlympics: The Latest

Listen to the latest news from the 2026 Winter Olympics.

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