5 Shocking Revelations Chelsea Handler Made About Dating 50 Cent In Her Latest Interviews

The unlikely romance between outspoken comedian Chelsea Handler and hip-hop mogul 50 Cent (Curtis Jackson) remains one of Hollywood’s most memorable brief flings. While their relationship took place back in 2011, Handler has recently revisited the details in a series of candid, hilarious, and fresh interviews on top-tier podcasts. As of December 12, 2025, the latest revelations offer a deeper, more personal look into the dynamic between the two stars, from the surprising reason for their split to the extravagant purchase Handler made in a failed attempt to impress the G-Unit icon. This article dives into the juiciest, most current details Handler has shared about her time with the rapper she affectionately calls a "sweetheart."

The pair’s connection began after 50 Cent appeared on her late-night talk show, Chelsea Lately, in 2009. Although they only dated for a few months in 2011, the public fascination has never waned, largely due to Handler’s unfiltered retrospective commentary on the relationship with one of the most powerful figures in entertainment.

The Complete Profile: Chelsea Handler and Curtis "50 Cent" Jackson

The story of their brief but highly publicized romance is best understood by reviewing the stellar careers of the two stars involved:

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Chelsea Handler (Comedian, Author, Host)

• Full Name: Chelsea Joy Handler
• Born: February 25, 1975 (Age 50 as of 2025)
• Birthplace: Livingston, New Jersey, U.S.
• Occupation: Comedian, Actress, Author, Television Host, Producer
• Notable Works: Chelsea Lately (2007–2014), Are You There, Vodka? It’s Me, Chelsea (book), Chelsea Does (Netflix documentary series), Chelsea (Netflix talk show), Evolution (stand-up special)
• Signature Style: Unapologetic, self-deprecating, and often focused on sex, drinking, and celebrity culture.
• Key Entities: E! Network, Netflix, Ted Harbert, Jo Koy, Stand-up comedy, Late-night television, Call Her Daddy podcast.

Curtis "50 Cent" Jackson (Rapper, Actor, Mogul)

• Full Name: Curtis James Jackson III
• Born: July 6, 1975 (Age 50 as of 2025)
• Birthplace: South Jamaica, Queens, New York, U.S.
• Occupation: Rapper, Actor, Television Producer, Businessman
• Notable Works: Get Rich or Die Tryin’ (album), Power (Starz television series), In Da Club (hit single), G-Unit (hip-hop group/brand), Sire Spirits (business venture)
• Signature Style: Entrepreneurial prowess, gritty storytelling, and a knack for producing hit television.
• Key Entities: Dr. Dre, Eminem, Starz, G-Unit Films and Television, Power Book II: Ghost, Hip-hop culture.

The Hilarious Reason Handler Called It Quits

In a recent appearance on the House Guest podcast with Scott Evans, Handler offered a surprisingly candid and comical explanation for why her whirlwind romance with the "In Da Club" rapper ultimately failed. Handler, known for her love of a good time, revealed that her biggest disappointment in dating the G-Unit mogul was tied to his lifestyle.

“He doesn't do drugs, which was the biggest disappointment,” Handler confessed. She elaborated that she was looking for a "partying partner" and a companion to engage in her famously wild lifestyle, but 50 Cent was completely sober. The revelation highlights the fundamental difference in their personal habits: while Handler was looking for a co-conspirator in chaos, Jackson, a successful businessman and father, maintained a much cleaner lifestyle. Despite this, Handler consistently praised his character, stating he was "one of the sweetest people" she had ever dated and a "sweet guy."

The Infamous "Chocolate Bentley" Story

One of the most viral and talked-about moments from Handler's recent interviews is the story of a ridiculously extravagant car purchase she made solely to impress 50 Cent. Handler admitted that she was so smitten with the rapper that she decided to buy a car that she thought would make her look compatible with the hip-hop star’s luxury lifestyle. She chose a high-end vehicle in a very specific, memorable color.

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“So I went and bought a chocolate Bentley and then we broke up,” Handler shared, adding a self-deprecating punchline: “So there I am stuck with this chocolate Bentley like a f*ing white dumb b**.” The anecdote perfectly captures Handler’s signature self-mocking humor and the absurdity of trying to keep up with a mogul like 50 Cent. The rapper, for his part, later commented on the story, acknowledging the humor and the sentiment behind the grand gesture. This story, frequently mentioned in her latest press cycle, has become a cornerstone of the Handler-50 Cent lore, showcasing the comedian's willingness to overspend for love.

The Surprising Public Backlash and Its Impact

While the relationship was short-lived, it generated massive public interest and, according to Handler, a significant amount of criticism. During a reflection on the Call Her Daddy podcast, Handler discussed the unexpected public reaction to her dating a Black man.

Handler revealed that the backlash she received was a major factor in the relationship's high-profile nature. She recalled facing considerable public criticism, much of which she felt was racially charged. This experience highlighted the societal complexities and prejudices that still exist, even for a high-profile, outspoken figure like Handler. She noted that the experience was eye-opening, adding a layer of seriousness to an otherwise comedic relationship retrospective. Despite the controversy, Handler’s friends apparently "loved" 50 Cent, which she also shared in the same interview, confirming his genuinely sweet nature.

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How 50 Cent "Convinced" Her to Date Him

The initial spark between the two stars began when 50 Cent made his appearance on Chelsea Lately, but Handler recently detailed the specific, persuasive way the rapper convinced her to go on a date. Unlike her typical preference for no-strings-attached flings, 50 Cent was persistent and charming.

Handler explained that the rapper approached her with a combination of flattery and persistence that she found endearing. She recounted that he managed to cut through her usual defenses, calling him "such a sweet guy" in a new revelation. The dynamic was a unique blend of Handler’s sharp wit and 50 Cent’s unexpected tenderness, which contrasted sharply with his tough public persona. This willingness to be vulnerable about how he won her over showcases a softer side of the G-Unit mogul that the public rarely sees, validating Handler's consistent praise of his character.

The Ongoing, Amicable Relationship and Political Spats

Despite their breakup, the relationship between Chelsea Handler and Curtis Jackson has remained remarkably amicable and public. Handler has often referred to him as her "favorite ex." Their interactions have continued to make headlines, most notably when their political views clashed publicly.

In the lead-up to the 2020 election, 50 Cent publicly supported Donald Trump, which prompted a humorous but pointed response from Handler. She famously offered to pay his taxes if he reconsidered his political stance, highlighting their ongoing, playful, and occasionally controversial public dialogue. While they are no longer romantically involved, their shared history and mutual respect—peppered with Handler’s comedic jabs—continue to make them a fascinating pair in the celebrity landscape. Handler’s latest interviews serve as a testament to the brief but impactful nature of their time together, cementing the legacy of their unlikely romance in pop culture history.