Chelsea Handler Spills the Details on Her Wild Romance with 50 Cent and Taking Back the Chocolate Bentley She Bought Him
Comedian Chelsea Handler recently shared a humorous revelation about her brief romance with hip-hop mogul 50 Cent, detailing how she unknowingly one-upped his luxury car game during their relationship in 2011.
During an appearance on the “Call Her Daddy” podcast with host Alex Cooper, Handler recounted how the Queens-born rapper would arrive at her residence each evening in a different high-end vehicle, creating quite a stir among her friend group.
“All my friends loved it because he’d come over to our house every night in a different car — a Lamborghini one day, then a yellow Ferrari the next,” Handler explained. The rotating lineup of exotic cars became a nightly spectacle that her friends couldn’t wait to witness.
What Handler didn’t realize at the time was that 50 Cent wasn’t purchasing these luxury vehicles but rather leveraging his celebrity status to borrow them from dealerships, a common practice in entertainment circles.
In response to his popping car game, Handler made what she now considers a hilarious miscalculation.
“I went and bought a chocolate Bentley because he kept coming over every night with a different car. I didn’t know you could borrow cars as a celebrity,” she admitted with characteristic frankness.
The purchase became even more notable after their relationship ended.
“There I was, stuck with this chocolate Bentley for two years, driving around like I’m some rapper,” Handler reflected, adding that while it was “a really nice car,” the situation perfectly captured the absurdity of dating in Hollywood — especially when one from one world steps into the hip-hop space.
The story has sparked widespread reaction on social media.
When “Entertainment Tonight“ put up an Instagram post about Handler’s Bentley story, many people commented on 50 Cent’s lasting impact on his former partners.
“50 will keep these women talking bout him for years,” one Instagram user observed.
Others pointed out how the anecdote reflects positively on the rapper’s character.
“He must really be a decent human being seeing as people he was involved with romantically speak so highly of him,” another social media user noted.
Another added, “Why are so many surprised 50 cent is a perfect gentleman and loveable bear and Chelsea is the perfect addition.”
The comments section took an interesting turn when one user quipped, “Vivica typing and deleting,” referencing 50 Cent’s relationship with actress Vivica A. Fox.
The reference struck a chord, as Fox had made headlines in 2023 and 2024 when she described 50 Cent as the “love of her life.”
She even entertained the idea of rekindling their relationship, drawing parallels to other celebrity couples who have reunited after years apart.
Looking at the standup’s chatter about him and reflecting on what the “Set It Off” actress has said, one commenter observed, “Good. That’s great for 50. When your ex talks positively about you.”
In a 2020 Instagram post promoting her standup special, Handler even referred to 50 Cent as her “favorite ex” and a “big fat teddy bear.”
One person suggested after listening to the story that it wasn’t all peaches and cream, and that she did what some white women do when dating Black men and dabbling in Black culture.
“She [Handler] called him the n word when they broke up and she admitted it on Howard stern,” one person said.
This is possibly not accurate.
While on the shock jock’s show, according to the St. Louis American, Handler recounted an argument with 50 Cent that led to their breakup. She admitted to calling him something “probably the worst thing you could say to a black person, short of calling him the N-word.”
Handler elaborated that she referred to him as “a street person, basically, something along the lines of being a gangster,” which she acknowledged was highly offensive.
Despite their past, Handler has since referred to 50 Cent as her “favorite ex,” demonstrating how time has transformed their brief romance into a source of entertaining memories.
The greatest quote came in a form of offered wisdom to anyone listening to Handler: “Life tip: always be yourself. Never try to be anything to impress anyone.”
According to New York Post, the comedian has moved forward in her career, currently hosting her third Critics Choice Awards and launching her first Las Vegas residency, while 50 Cent continues to expand his entertainment empire through various business ventures and production projects.
He also just finished his first Las Vegas residency, where he received mixed reviews.
The chocolate Bentley story has become one of Handler’s favorite anecdotes about her love life, perfectly capturing the unique intersection of celebrity, romance, and automotive extravagance in Hollywood.
It serves as a reminder that even in the glittering world of entertainment, sometimes the most memorable moments come from our most impulsive decisions.