Sleepy Brown Reveals Secret Beef Between OutKast, Diddy, and Biggie Smalls

We’re living in a golden age for millennials who love the memories of their yesteryears, as more than ever, entertainers who made big splashes in the late 90s and early 2000s are opening up on podcasts about their time in their respective industries. Joining the mix of celebrity podcasters is Grammy-winning rapper Killer Mike, who hosts Conversate with Killer Mike. On a recent January episode, the Grammy-nominated producer, writer, and artist, Sleepy Brown, stopped by. 

For those who don’t know, Brown is a member of the Atlanta-based production team, Organized Noize. The team was behind some huge R&B and rap hits of the 90s and 2000s, including TLC’s “Waterfalls” and Ludacris’ “Saturday (Oooh! Ooooh!)", and a slew of OutKast classics such as “So Fresh, So Clean”, “Player’s Ball”, and “Spaghetti Junction”. Given Brown’s proximity to Outkast, he has plenty of personal stories to share, and boy did he share one. He has social media buzzing after revealing a secret past beef between his frequent collaborators OutKast and Bad Boy’s Diddy and Biggie Smalls. 

How Biggie Smalls’ “Big Poppa” Music Video Kicked Off Drama

After Killer Mike brought up Bad Boy founder Diddy, Brown eventually says:

“Diddy cool, he cool, but he was a little funny, arrogant that I didn’t like. I’m going to be true. Him and Rico [Rico Wade of Organized Noize] always had this like competition with them, but like friendly competition. Puffy cool… But honestly back then we were in competition with each other because I felt like he was biting the sh*t out of us bro. I’m going to tell you this, OutKast Southern Playalist video. Go look at the way my boys wear their hats. The way Dre wore that Kangol and the way Big Boi wore his hat to the side. Then go look at Biggie’s video where that n*gga goes to the bar and mush n*ggas in the face to get to the girl, he’s talking about Kast.”

Now for a point of clarification, the Biggie video Brown was referring to was the “Big Poppa” video. In the visual, Biggie walks up to the bar and pushes a guy wearing a sideways white cap out of the way in order to talk to a woman. 

Also in the podcast interview, Brown proceeds to imply that Biggie wasn’t wearing Kangol hats until OutKast started popularizing them, and that Biggie was “Timbaland's.” Furthermore, Brown claims that because the musical collective known as the Dungeon Family (which includes OutKast) was offended by Biggie and Diddy stealing their style and felt like the “Big Poppa” video was disrespectful, the Dungeon Collective confronted Diddy and Biggie at Da Brat’s video shoot for “Give It 2 You.” However, no one came to blows. Check out Brown’s full story below. 

Sleepy Brown says Biggie dissed OutKast in the “Big Poppa” music video, which led to the Dungeon Family confronting Diddy & Biggie on their tour bus, & says Biggie also took OutKast’s style of wearing Kangol hats.

(???? Killer Mike/YouTube)
pic.twitter.com/Oj6NlWk0qa

— The Art Of Dialogue (@ArtOfDialogue_) January 23, 2026

The OutKast and Biggie Small Videos in Question

Being inquisitive, I decided to take a look at the throwback videos. First up, you’ll see OutKast’s “Southernplayalisticadillacmuzik” video, which was released around April 1994, and Andre 3000 is certainly wearing a Kangol. And below that, you’ll see Biggie’s “Big Poppa” video that debuted in December 1994. Biggie is also wearing a Kangol. That being said, feel free to draw your own conclusions.

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