Pop Culture

Chelsea Handler Says 'A Lot of Rappers' Slide in Her DMs

The comedian and podcaster famously counts 50 Cent among her former beaus.

NEW YORK, NEW YORK - MARCH 25: Chelsea Handler is seen on March 25, 2026 in New York City.
Raymond Hall/GC Images

50 Cent isn’t the only rapper to have shown romantic interest in comedian Chelsea Handler.

Handler was a guest on a recent episode of Watch What Happens Live with Andy Cohen, where she was asked to reveal at least one famous name who’s slid in her DMs. While Handler drew a blank on the person’s name, she mentioned that a “big rapper” had previously hit her up.

“I don't want to say the wrong guy. Shoot. But they're all in my DMs,” she said. “A lot of rappers slide into my DMs. But there was a really big one that I screen grabbed and sent to my friends, but I can't fucking remember his name.”

Handler added that she was DMed by the person in the past year.

The rapper that the television personality and podcaster has most referenced is 50 Cent, who Handler briefly dated in 2010. In January, Handler appeared on podcast We Might Be Drunk, where she praised the artist and media mogul for being “relentless” against his longtime rival, Diddy, and dubbed herself Fif’s favorite ex-girlfriend.

"I'm the only one he doesn't ever talk shit about," Handler said on the podcast. "Apparently… he talks shit about all of his exes, and I'm one of the only ones he talks about respectfully."

One month before, Handler visited Sean Evans’ web series House Guest, where she detailed how Fifty asked her out and recounted the “racist” criticism about their relationship.

“I don't allow myself to get upset about things like that. But I think at that point in my career, people were just, like, I mean — it was just kind of racist, this backlash," she said on the show.

Last February, Fif expressed his “love” for Handler after she admitted to once buying a chocolate Bentley to impress him while they were dating.

Related Stories

Chelsea Handler, 50 Cent
pop-culture

Chelsea Handler Says She’s 50 Cent’s Favorite Ex, Praises His Diddy Troll Campaign

Handler also teased 50 at the Critics' Choice Awards over his Diddy doc involvement.

Mark Elibert107 days ago
Split image of Chelsea Handler and 50 Cent.
Jose Martinez119 days ago
(L-R) Chelsea Handler and 50 Cent.
pop-culture

Chelsea Handler Recalls 50 Cent Romance Backlash: ‘It Was Just Kind of Racist'

"He's such a sweet guy," the comedian said of the G-Unit mogul, recalling their short-lived relationship.

Stay ahead on Exclusives

Download the Complex App