Chelsea Handler and 50 Cent’s brief romance resurfaces after 'The Roast of Kevin Hart'

Chelsea Handler found herself back in the spotlight after her sharp-tongued appearance at The Roast of Kevin Hart, and with it came renewed fascination over one of her most unexpected past relationships: her brief romance with 50 Cent.

Handler was one of the standout celebrity roasters during the Netflix live special at the Kia Forum in Los Angeles, where her no-filter jokes quickly sent social media digging back through old interviews, photos, and celebrity lore. Among the stories that resurfaced most quickly was her short-lived but long-remembered relationship with 50 Cent.

The pair first crossed paths in 2010 when the rapper, whose real name is Curtis Jackson, appeared on Handler’s late-night show, Chelsea Lately. What started as a guest appearance soon turned into one of Hollywood’s more unexpected celebrity pairings.

Handler later recalled that 50 Cent was persistent after the show, sending dozens of roses to her office and repeatedly calling. At first, she was reluctant. But after inviting him to one of her comedy shows in New Orleans, she said she saw a side of him that surprised her.

She has since described him as “the complete antithesis” of what people might have expected and has often referred to him as her “favorite ex-boyfriend.”

Even though the romance lasted only a few months, it generated outsized attention. Fans and tabloids alike were fascinated by the unlikely pairing, a sharp, politically irreverent comedian and the rapper behind In da Club.

By 2011, Handler confirmed that the two had dated “very casually.” Over time, she also shared why the relationship didn’t last. She admitted she was uncomfortable with the lavish gifts and expensive gestures that came early on, saying she preferred not to be showered with extravagant presents by someone she barely knew.

One of the funniest stories to survive from that relationship came years later, when Handler revealed that she once bought herself a chocolate-colored Bentley while dating 50 Cent.

She said he would constantly show up in flashy cars, Ferraris one day, Lamborghinis the next — and she assumed he owned them all. Wanting to play along, she impulsively bought herself a Bentley, only to later realize celebrities often borrow exotic cars for appearances. Soon after, the relationship ended, leaving her stuck with the luxury purchase.

That story has since become one of Handler’s favorite celebrity-dating anecdotes — and one fans still bring up whenever her romance with 50 Cent resurfaces.

Her appearance at Kevin Hart’s roast brought all of it back into the conversation. Years after the relationship ended, the pairing still feels oddly memorable, partly because it was so brief, and partly because it was so unexpected.

For Chelsea Handler, it remains one of those rare Hollywood flings that lasted only months but somehow never really left the headlines.