Chelsea Handler had nothing but praise for 50 Cent during a recent appearance on the We Might Be Drunk podcast—especially when it comes to his long-running habit of publicly criticizing Diddy.
“I love what he’s doing to Diddy,” Handler said, laughing as she doubled down on how relentless 50 has been. “He’s great.” She even joked that his antics might be reason enough to consider getting back together with him, sparking laughs from the hosts.
The conversation also turned reflective as Handler looked back on her brief relationship with 50 Cent in the early 2010s. According to her, she holds a unique position among his former partners. “I’m the only one he doesn’t ever talk sh*t about,” she claimed, adding that she’s one of the few exes he still speaks about respectfully. “I was a dream,” she said, confidently.
Handler has continued to reference 50 Cent publicly, including during her time on stage at the Critics’ Choice Awards, where she cracked a joke comparing a Netflix music movie to a fictional project titled 50 Cent: Diddy Hunter.
The punchline lands because 50 Cent has spent years taking aim at Diddy on social media. That feud intensified after the Bad Boy Records founder faced legal troubles last year, culminating in a conviction on two counts related to transportation to engage in prostitution. Diddy is currently serving a 50-month prison sentence.
Beyond online trolling, 50 Cent also expanded his commentary into long-form media. He served as an executive producer on the Netflix docuseries Sean Combs: The Reckoning, which explores multiple allegations surrounding the embattled mogul. The series features appearances from figures like Aubrey O’Day, Al B. Sure!, and Mark Curry.
Diddy’s legal team pushed back hard before the docuseries premiered, calling it a “hit piece” in a statement shared with The Hollywood Reporter. They also criticized 50 Cent’s involvement, describing him as a longtime adversary who has publicly mocked Combs for decades.
Still, from Chelsea Handler’s perspective, 50 Cent’s unfiltered approach remains entertaining—and maybe even a little charming. At the very least, it’s given her plenty of material for jokes, fond memories, and a headline-grabbing podcast moment.
