Chelsea Handler may have dated 50 Cent only briefly, but their time together often makes it back to the headlines, as it did after the live premiere of Netflix's 'The Roast of Kevin Hart'.
Comedian Chelsea Handler has returned to the headlines for her much-talked-about relationship drama with popular rapper 50 Cent after her appearance on Netflix's newly released The Roast of Kevin Hart. The live Netflix special, which aired on Sunday, May 10, 2026, featured Chelsea as one of the celebrity roasters, and her performance has sparked renewed interest regarding the time she dated the In Da Club rapper, one that ended on a hilarious note, as per the comedian herself.
Amid renewed interest in the comedian's past, including the time she attended a Jeffrey Epstein dinner, the internet is once again digging up past interviews and photos of her unexpected romance with her "favourite ex-boyfriend."
The much-talked-about Netflix live special took place at the Kia Forum in Los Angeles as part of the Netflix Is A Joke Festival, featuring a lineup of celebrities and comedians taking brutal shots at Kevin Hart throughout the night. With Chelsea Handler being one of the celebrity roasters, she immediately grabbed attention with her classic, no-filter comedy. During the event, comedian Shane Gillis took a controversial jab at Chelsea Handler, referencing the one time she attended a Jeffrey Epstein dinner. Handler’s fiery comeback and scene-stealing presence quickly sent the internet down a rabbit hole, with social media users revisiting several controversies from her past, especially her headline-making romance with rapper 50 Cent.
Chelsea Handler and 50 Cent were a thing back in the early 2010s, when they dated for a while. Even though their romance barely lasted a few months, it somehow turned into one of Hollywood's most unforgettable and unexpected celebrity pairings. Even more than a decade later, here we are, still talking about it.
The duo first got together in 2010 after 50 Cent (real name Curtis James Jackson III) appeared on the comedian's popular late-night show, Chelsea Lately. Their relationship instantly became a talking point for fans and celebrity circles alike, given the unexpected match. Speaking about how they got together, Handler shared during a December 2025 interview on the House Guest podcast:
"He convinced me to date him after he was on my show. It was like a Friday that he was a guest, I think. And then, I came in over the weekend, and there were like dozens and dozens of roses in my office. My assistant said, 'Curtis Cent has called three times.' I was like, 'Who's Curtis?' She's like, 'Fiddy.'"
She revealed how she didn't want to talk to him initially, but "Curtis was sweet." When she told the rapper that she won't go out with him, she invited him to see one of her comedy shows in New Orleans and said they could grab a drink afterward. She realised how sweet Curtis actually was in real life, even once calling him "the complete antithesis of what you’d imagine." Handler later admitted that the public reaction to their relationship became much bigger than either of them expected. "People were like, ‘What are these two doing together?’" she said while reflecting on the romance.
While their romance sparked intense gossip, it ended within a few months, and reports suggest the breakup wasn't smooth. The comedian-actress has openly spoken about their brief romance over the years and even called Curtis her "favourite ex", but speculations were rife at the time that the latter still had lingering feelings for his former girlfriend, Ciara, which may have contributed to their split.
After months of speculation about whether they ever made their relationship official, Handler confirmed in a 2011 interview with Piers Morgan that they "dated, very casually." Handler also cited some 'faults' that didn't sit well with her, mentioning his overt attempts to woo her, and she ended up returning the expensive presents he got her. She explained:
"I don’t really like when men buy me ridiculous gifts, especially when I don’t know them well... I can buy my own gifts. I really don’t like gifts from rappers in general, since I’m not a hooker."
One of the most popular anecdotes of Handler and 50 Cent's brief romance was the time the former purchased a luxury car of her own. During a 2025 interview with Alex Cooper on the Call Her Daddy podcast, the comedian revealed how she impulsively bought herself a chocolate-colored Bentley while dating the rapper, thinking he actually owned the luxury cars he kept driving around daily.
Chelsea revealed her friends loved 50 Cent a lot because he'd "have like a Lamborghini one day and then like a yellow Ferrari the next day." Only later did she realise celebrities often borrow exotic cars from dealerships for appearances. So, even when their relationship was over, she was stuck with her expensive car. The comedian jokingly shared:
"I got a chocolate Bentley because he kept coming over every night, and he had a different car, so, as a joke, I went and bought one. I didn't know you could borrow cars as a celebrity...and then we broke up. So there I am stuck with this chocolate Bentley like a f***ing white dumb bitch a**hole driving around like I'm some rapper..."
The story has since become one of the funniest celebrity dating anecdotes fans still reference today. Despite the resurfaced controversies and renewed relationship drama, Handler, 51, is living her life unapologetically, and recently soft-launched a new relationship earlier this year.
Thanks to the Kevin Hart roast, fans are once again revisiting the chaotic, entertaining, and unforgettable connection with her "favourite ex-boyfriend"!
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