Home / Arts and Entertainment / Chelsea Handler & 50 Cent: The Bentley Story
Chelsea Handler & 50 Cent: The Bentley Story
11 May
Summary
- Handler joked about buying a Bentley impulsively during her romance with 50 Cent.
- The comedian's appearance on Kevin Hart's roast revived interest in past relationships.
- Handler and 50 Cent dated briefly in the early 2010s and their romance ended.
- Handler once said she doesn't like gifts from rappers as she is not a hooker.
Chelsea Handler's recent appearance on Netflix's "The Roast of Kevin Hart" on Sunday, May 10, 2026, has sparked renewed interest in her past relationships, particularly her brief romance with rapper 50 Cent. The comedian's no-filter performance at the Los Angeles event led social media users to revisit notable moments from her life.
Handler and 50 Cent, whose real name is Curtis James Jackson III, dated in the early 2010s after he appeared on her show "Chelsea Lately." Their unexpected pairing became a significant talking point. Handler shared that 50 Cent convinced her to date him, initially sending dozens of roses to her office.
Despite the public fascination, their relationship lasted only a few months. Handler cited issues like receiving excessive gifts, stating she doesn't like gifts from rappers as she is "not a hooker." There were also speculations about 50 Cent's lingering feelings for his ex-girlfriend, Ciara.
A memorable anecdote Handler shared was impulsively buying a chocolate Bentley. Believing 50 Cent owned the various luxury cars he drove, she purchased one herself, only to later realize celebrities often borrow such vehicles. She humorously described being stuck with the Bentley after their breakup.
