The brief, highly publicized, and unusual romance between hip-hop mogul 50 Cent (Curtis Jackson) and comedian Chelsea Handler in the early 2010s was a source of constant media fascination. However, it was Handler herself who provided the most hilarious anecdote about their relationship, revealing a massive and costly misunderstanding that proved their chemistry was based on comedy gold.
Borrowed Ferraris, One Bentley, Total Chaos — 50 Cent Flaunts Fake Supercars to Woo Chelsea Handler, She Buys Him a Bentley in the Funniest Dating Twist Ever.
The story, which Handler has hilariously recounted on various talk shows and podcasts, centered around 50 Cent’s transportation choices during their dating period. During the early phase of their courtship, Handler noticed something odd: he seemed to own an extremely vast and diverse collection of high-end luxury cars, cycling through them almost daily. Handler recalled seeing him show up repeatedly in different supercars, including various Lamborghinis and yellow Ferraris. She admitted that her friends “f***ing loved” this extravagant display.
This led the comedian to a natural, but incorrect, conclusion: she believed 50 Cent was a passionate car enthusiast who loved collecting and driving exotic vehicles. Mistaking his constantly rotating fleet of cars as a deep love for automotive novelty, Handler decided to make a grand, extravagant gesture that would impress her new beau.
Based on this hilarious misinterpretation of his vehicle rotation, Handler purchased a luxury car as a gift. Notable Event: Chelsea Handler bought a “chocolate Bentley”—one of the world’s most luxurious and expensive automobiles.
The story reached its comedic climax when Handler realized the hilarious truth behind the rotation: the Ferraris and other supercars he had been driving were mostly borrowed. As Handler later revealed, she realized, “he was borrowing all these cars from different dealerships. I was like, ‘You can do that?'” She admitted she bought the Bentley “as a joke” but quickly became the punchline herself.
The unfortunate timing meant the expensive gesture was revealed to be a profound and funny misunderstanding, and shortly after, the relationship ended. Handler found herself “stuck with this chocolate Bentley like a fing white dumb bh a**hole driving around like I’m some rapper,” a situation she endured for about two years.
50 Cent may be a business genius and a millionaire, but Chelsea Handler proved that even a wealthy mogul can leave a date confused enough to spur the purchase of a Bentley, all thanks to a misread of his temporary transportation choices.