Chelsea Handler Mentioned Her ‘Favorite Ex,’ 50 Cent, at the Critics Choice Awards

50 Cent has been in the news a lot lately. Between his online trolling activities and Netflix documentary, the “Many Men” rapper has a lot going on. His activity has grabbed the attention of one of his exes, too. Chelsea Handler called him out during her recent Critics’ Choice Awards monologue, calling 50 Cent a ‘Diddy Hunter.’ 50 Cent and Handler actually have a history; they dated very briefly. While the relationship was short-lived, Handler has repeatedly referred to 50 as her ‘favorite’ ex.

Chelsea Handler mentioned 50 Cent in her recent monologue

Chelsea Handler’s Critics’ Choice Awards monologue included a mention of 50 Cent and his relentless efforts to expose Sean ‘Diddy’ Combs. During the lengthy monologue, she mentioned that the cast of the animated flick,  KPop Demon Hunters, was in the house, then joked that no one should confuse the flick with Netflix’s other 2025 hit, 50 Cent: Diddy Hunter.

Handler’s joke referenced the surprise release of Sean Combs: The Reckoning. The Netflix docuseries that 50 Cent had teased a year before the announcement was released in December. 50, who sourced never-before-seen footage of Diddy, served as the series’ executive producer. The docuseries has made serious waves in the industry. While 50 Cent is heavily streamed, a small minority of music artists and rappers have criticized him for getting involved in Diddy’s business and profiting from it. The series is the culmination of a decades-long feud that Diddy once insisted was one-sided.

How long did the duo date?

While Chelsea  Handler’s mention of 50 Cent might simply feel like a timely addition to a largely comedic monologue, there is more to the story than that. The TV host and the rapper actually dated, albeit briefly. During an appearance on House Guest, Handler revealed that 50 Cent pursued her after he appeared on her talk show back in 2010 or 2011.

She said she returned to the office after his appearance and found that he had sent her flowers. She went on to say that she had been hit on plenty by men in the industry, but it was mostly “play.” Handler then said it felt “different” with 50, and that he had been sweet. They dated for a few months, though things didn’t turn serious, and they split amicably. She sometimes refers to him as her “favorite ex.”