We chart Diddy’s rise from musician to mogul, from the center of hip-hop to the center of American culture. But that rise wasn’t always a smooth ascent. Along the way, he had moments of alleged violence and brushes with the law. Were these lapses in judgment or serious red flags that signaled a darker side to his success? Learn more about your ad choices. Visit podcastchoices.com/adchoices
Chapter 1: What major event shaped the 1995 Source Awards?
On an August night in 1995, the four corners of the hip-hop world gathered at the Paramount Theater in Midtown Manhattan. Artists from the South, the Midwest, and from the East and West Coast were all under the same roof.
It's the Source Hip-Hop Musical Board!
They were all there for the second annual Source Awards. It was a celebration of hip-hop, a music genre that was rapidly moving from underground to mainstream. The event felt like a pretty standard award show. An eager crowd filled the auditorium waiting to hear the results.
And the winner is...
West Coast rapper Snoop Doggy Dogg, also known as Snoop Dogg, won Artist of the Year. East Coast rapper The Notorious B.I.G. won Album of the Year for Ready to Die. And Outkast, a duo from Atlanta, won Best New Artist of the Year. The night was filled with performances and acceptance speeches. And one of those speeches turned the 1995 Source Awards into one of hip-hop's most infamous nights.
Yeah, yeah. Record executive Suge Knight and rapper Danny Boy won the award for Best Motion Picture Soundtrack for their work on the movie Above the Rim. Suge climbed on stage in a bright red button-down shirt. First of all, I'd like to thank God. Suge is not a small guy by any stretch of the imagination. He stands at maybe 6'2", and is definitely over 260 pounds.
Before he got into the music business, he spent a year in the NFL as a defensive end for the Los Angeles Rams. In 1995, he was running one of hip-hop's two big record labels, Death Row Records out of LA. Now, after thanking God, Suge didn't go on to give a standard acceptance speech.
The crowd had an immediate reaction. Some applauded, but lots of people booed when Suge said that any artist who didn't want their producer in their videos and songs should work with his company, Death Row.
Everyone knew who he was talking about, Sean Diddy Combs, or, as he was known back then, Puff, Puffy, or Puff Daddy, the head of the other big hip-hop label, Bad Boy Records, based in New York City. Unlike most producers and record execs, Diddy wasn't happy just sitting in the crowd or getting on stage to accept an award. He was an aspiring rapper himself and craved the spotlight.
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Chapter 2: How did the rivalry between Diddy and Suge Knight escalate?
Suge Knight and Diddy were already rivals, businessmen vying for their record label to be king. But Justin Tinsley, a reporter at ESPN's sports, race, and culture outlet, Anscape, says Suge's speech at the Source Awards was a turning point. their rivalry became much darker. About a month after the awards, they were both in Atlanta for the birthday party of a rapper and producer, Jermaine Dupri.
Tinsley says tensions between Suge and Diddy and their entourages were high.
Sides get to barking with each other, things spill out in the parking lot, and one of Suge's closest friends is murdered in the parking lot.
Atlanta police said Diddy's bodyguard, Anthony Wolf Jones, was their prime suspect. Jones' attorney said he had absolutely nothing to do with the shooting, and no one was ever charged. But the shooting made the friction between Diddy and Suge worse. And that's partly because their beef was part of something much bigger, the East Coast-West Coast rap rivalry.
Chapter 3: Who were the key figures in the East Coast-West Coast rap feud?
which people have obsessed over for decades and we could probably write a whole other podcast about. But here's what you need to know to understand what happened next. Diddy represented one of the East Coast's biggest rap stars, the Notorious B.I.G., or Biggie Smalls. Suge Knight represented one of the biggest West Coast rappers with his own unique approach to music, Tupac Shakur, or Tupac.
and both rappers and their styles were vying to be the biggest in the country. So the beef between Diddy and Suge was also connected to a rivalry between Biggie and Tupac. And I'm not just talking about a couple of diss tracks like Kendrick and Drake today. Tupac was shot and killed in 1996. Biggie was shot and killed in 1997.
The two stars, only in their 20s and at the start of promising careers, were suddenly dead. Their murders captured international attention and really marked this era of hip-hop music. Their deaths also generated tons of unsubstantiated theories. In particular, there were theories that each rapper was killed by someone tied to their rival's label.
No one has been convicted for either Tupac or Biggie's deaths. But this is the bottom line. A feud heated up after Suge Knight publicly called out Diddy's need for attention.
The only two people left were the label heads. Suge's career was never truly the same after Tupac's murder. Death Row pretty much crumbled in the months after that. But Diddy? Diddy became an even bigger star.
Just like at the Source Awards, Diddy took center stage. He put out his first album as Puff Daddy in 1997, the same year Biggie died. It was called No Way Out and included the hit song I'll Be Missing You, a tribute to Biggie featuring his widow Faith Evans, who was also an artist on the Bad Boy label.
I know you're still living your life after death.
That song was the first hip-hop song ever to debut at the top of the Billboard 100. And that year, Diddy received seven Grammy nominations, including for Best New Artist.
And now Diddy is an established artist on top of an already established executive. So his star power really began to rise.
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Chapter 4: How did Diddy rise to prominence in the music industry?
Hey, I'm Brad Milkey. You may know me as the host of ABC Audio's daily news podcast, Start Here, but I'd like to add aspiring true crime expert to my resume. And here's how I'm going to make it happen. Every week, I'm going to unpack the biggest true crime story that everyone is talking about.
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Before Sean Diddy Combs was crowned the new king of hip-hop by Rolling Stone, he was a kid with a temper. In fact, that's why he says he got the name Puffy. He'd huff and puff whenever he got angry. Combs was born in Harlem, but grew up about 10 miles north in Mount Vernon, New York. Writer and music journalist Toray interviewed Diddy many times.
His father was from the streets of Harlem, and he was very proud of the heights that his father rose to in that culture. But he's really a suburban guy.
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Chapter 5: What controversies marked Diddy's early career?
Diddy wanted to be at the pulse of music too, and his determination to get the internship paid off. He dropped out of Howard his sophomore year and started promoting rappers in New York City, really starting to build his music network while interning at Uptown Records. In 1991, he and rapper Heavy D organized a charity basketball game at the City College of New York.
It was advertised as a chance to see New York City rap stars like Run DMC and Boyz II Men compete on the court. And people flocked to the game. It was clear, even then, that Diddy understood how to create and market an event everyone wanted to go to. but he was young and inexperienced. The gym had a 2,700-person capacity, but almost 5,000 people showed up.
As the crowd rushed to get in, 29 people were injured and nine died in a stampede. One headline from that day read, "'The Carnage at City College.'" Days later, a 22-year-old Diddy gave a press conference at the Plaza Hotel in Manhattan. He looked so young, so defeated. At one point, he put his hand over his eyes and nose as if he were overwhelmed and exhausted.
I would like to let the families of the victims know how deeply hurt we all are.
That incident followed Diddy for years. In that same 1997 interview when Diddy was asked about capitalizing on Biggie's death, he was also asked to reflect on the City College stampede.
I've gone through a lot. I've seen a lot of tragedies. I've seen a lot of death in my short time. And I don't know why. Believe me, I ask myself the same question. Why have I been chosen to see all of this death at such a young age? At the end of the day, I have to also live with the fact that I was throwing a vent trying to do something good and something bad happened.
No criminal charges were ever filed for the Stampede, but civil lawsuits from victims and their families went on for years, directed at Diddy, Heavy D, and the City College of New York. A judge in one lawsuit filed by four victims found that Diddy, Heavy D, and the college were equally responsible for the injuries and deaths. Here's what really stands out to me about the City College Stampede.
When it happened in 1991, Diddy was, as the New York Times put it, a largely unknown rap promoter. Writer and music journalist Doré says Diddy was buried in bad press.
It seemed that this young guy had been too reckless and building whatever promotion career that he was trying to build. And surely this would be the end of his career.
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Chapter 6: What was the impact of the City College stampede on Diddy's career?
Those rappers were Craig Mack and Biggie Smalls, and Diddy knew what to do with their talent. Justin Tinsley, the reporter from ESPN's Anscape, says in particular, Diddy had a strong vision for Biggie.
Diddy and Biggie were one of the biggest tag teams. Biggie came roaring out the gates with a single called Juicy, which if you know Biggie's story, he didn't necessarily want to record that song at first. And it was Diddy's insistence that basically forced him to record that song. And obviously the song became a hip hop classic.
As Biggie became one of the most famous rappers in the world, Diddy signed more artists to Bad Boy. By 1997, the year Biggie died, Bad Boy had an impressive roster of talent, including The Lox, Mase, Faith Evans, and 112.
There was a time when it was ubiquitous, his records. I remember multiple nights of being in a club, they're playing a string of Bad Boy records, you get in a cab to go to another club, the radio is playing Bad Boy records in the cab, you get in the next club and they're playing Bad Boy as soon as you walk in. It was just everywhere.
And it wasn't just about the music. Bad Boyz artists had an era-defining style, a look, baggy, bold, flashy clothes.
They were really smart in that they followed the Motown playbook. There's a charismatic CEO who creates the brand and creates the image. There's a brand image that links them all together, and they're part of the culture.
But after an incredible rapid rise to the top of the charts in cultural power, Bad Boy hit somewhat of a sophomore slump.
There really wasn't much of an ability to create or recruit new superstars after that.
In 1998 and 99, Bad Boy put out new albums by Faith Evans, Total, and 112. But initially, only 112's album was meeting the high expectations for the Bad Boy label. What were those high expectations? The album's going platinum, selling more than one million copies quickly. Diddy's second album, Forever, was also not as successful as his first.
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Chapter 7: How did Diddy's business acumen contribute to his success?
It gave her some street credibility. She's doing, you know, records with rappers after this relationship. They definitely heightened each other's celebrity quite a bit. They were a big couple. They were a very influential couple.
The cover of Jet Magazine read, Puffy Combs and Jennifer Lopez, showbiz's most talked about couple. Other headlines said, call it chemistry, Jennifer Lopez and Puff Daddy. And Bright and Hot, superstar couple riding rollercoaster romance. A couple days before New Year's Eve in 1999, the influential couple went to a club near Times Square.
While they're in the club, there was a dispute with a guy named Scar, who's deceased now. Derek Parker is a retired NYPD detective who responded to the scene at the club. I think money was thrown in his face, or money was thrown at Diddy or something like that. A shooting broke out, and three people were injured. Diddy and Jennifer Lopez fled the scene and got into a car.
When they were pulled over, police say they found a gun in the front seat.
It was a lot of chaos back then. When we went to the precinct, there were over 300 reporters outside.
Two of entertainment's biggest stars spent much of this Monday after Christmas in a New York City police station. Jennifer Lopez and the rap mogul Sean Puffy Combs were held for possessing a stolen gun.
Prosecutors ultimately dropped the charges against Jennifer Lopez, but Diddy and his bodyguard were charged.
Today's indictment on two counts of criminal possession of a weapon carry a possible 15-year prison sentence if Combs is found guilty.
As the criminal case moved forward, news reports pointed back to the City College Stampede of 91 and the attack on Steve Stout earlier in 99. And they began to ask whether Diddy had a pattern of causing violence.
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Chapter 8: What setbacks did Diddy face in the late 1990s?
His relationship with Jennifer Lopez was much more compelling, more tantalizing. The couple was a mainstay on red carpets and eventually, Jennifer Lopez's fashion headlines drowned out the more negative press. There were two outfits in particular that really defied her time with Diddy.
One where she wears this all white outfit with this rhinestone bandana. You know, she's supposed to look like a hood girl and he's by her side in a coordinating outfit. And then there was of course the famous Versace dress.
That's a green and blue sheer dress she wore to the Grammys in 2000. It was so low cut, you could see her belly button.
Diddy was by her side when she wore that, you know? So he was really there for the moment in which J-Lo becomes J-Lo. This is when she becomes J-Lo as opposed to Jennifer Lopez.
And this is when Sean Puff Daddy Combs became Diddy.
Something Diddy's really good at doing is rebranding himself, right? So those name changes often came on the heels of a scandal or something unscrupulous about him being reported. You know, then he comes back, new name, new album, new era, new image.
After the break, his new image was all about being more than a rapper and record executive. It was focused on being an all-around mogul, someone even more powerful and unavoidable, even more invincible.
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