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Hip-hop mogul Sean ‘Diddy’ Combs isn’t in a position that anyone else wants to be in right now. The Bad Boy Records founder was arrested back in 2024 on charges of sex trafficking and racketeering, and ever since, he’s been sitting in jail awaiting trial.

Diddy has had his share of feuds through the years, including with rapper 50 Cent. After Diddy’s arrest, 50 freely spoke out about the allegations and charges. And in an old interview, Diddy revealed that he thinks 50 has “insecurities” around him.

Sean 'Diddy' Combs
Sean ‘Diddy’ Combs | Stephen Lovekin/Getty Images for The Jackie Robinson Foundation

Sean ‘Diddy’ Combs and 50 Cent have never really been friends

Diddy’s alleged feud with 50 goes back nearly 20 years. Back in 2006, 50 Cent released his song “The Bomb,” which alluded to Diddy having information about Notorious B.I.G.’s 1997 murder. The men’s beef continued into the mid-2010s when they both started representing different vodka brands. Still, Diddy has never really played into the feud. But during an episode of Andy Cohen’s Watch What Happens Live!, Diddy said that 50 has “insecurities” around him.

“He loves me,” Diddy said when he was asked about the alleged feud in 2018. When Cohen responded asking if 50’s feud-stirring remarks were out of love, Diddy replied with, “Or some insecurities … It’s things that people have to deal with, but I’m me; I’m here.”

Diddy said that he’s never taken 50’s insults “seriously” and suggested back then that the two don’t have any beef. “It’s not really a big deal to me,” he said.

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50 Cent called out Sean ‘Diddy’ Combs shortly after his arrest

50 didn’t waste any time saying, “I told you so,” to fans shortly after Diddy was arrested last September. “Now it’s becoming more full-facing in the news with the Puffy stuff, but away from that, I’m like, ‘Yo, it’s just my perspective because I stayed away from that stuff the entire time, because this is not my style,’” 50 told People back in October.

It didn’t take long after Diddy’s arrest for 50, along with G-Unit Film & Television, to announce that they plan to release a documentary about Diddy’s partying lifestyle and the allegations against him. “This is a story with significant human impact. It is a complex narrative spanning decades, not just the headlines or clips seen so far,” 50 told People. The docuseries will premiere on Netflix, though few details have been announced about what it will include.