5 Shocking Revelations About 50 Cent And Chelsea Handler's Wild, Brief Romance

The unlikely pairing of hip-hop mogul 50 Cent and late-night talk show host Chelsea Handler remains one of Hollywood's most bizarre and fascinating celebrity romances, a decade-old fling that continues to make headlines even as of late 2025. Their short-lived affair in the early 2010s was a cultural shockwave, melding the world of gangsta rap with sharp-witted, unfiltered comedy, yet the two have maintained a complicated connection that resurfaces in the news every few years.

Most recently, the story has gained fresh momentum after Handler opened up about their time together on a major podcast, revealing intimate and hilarious details—including a massive luxury purchase made just to impress the G-Unit general, Curtis Jackson. The narrative of their relationship, however, is not just one of brief passion; it’s also a tale of public political clashes and an enduring, if odd, mutual respect.

Complete Profile: Curtis Jackson III and Chelsea Joy Handler

The core of this compelling relationship lies in the stark contrast between the two individuals. Here is a brief look at the biographies of the hip-hop powerhouse and the comedy queen.

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Curtis "50 Cent" Jackson III Biography

• Full Name: Curtis James Jackson III
• Born: July 6, 1975, in Queens, New York
• Occupation: Rapper, Actor, Television Producer, Entrepreneur
• Notable Works: Albums Get Rich or Die Tryin' and The Massacre; Executive Producer of the Power television franchise.
• Early Life: Rose to fame with a streetwise rags-to-riches life story after overcoming a troubled youth, including being shot nine times.
• Known For: His business acumen, often referred to as a "hip-hop mogul."

Chelsea Joy Handler Biography

• Full Name: Chelsea Joy Handler
• Born: February 25, 1975, in Livingston, New Jersey
• Occupation: Stand-up Comedian, Actress, Writer, Television Host, Producer, Activist
• Notable Works: Hosted the late-night talk show Chelsea Lately (2007–2014) on E!; Hosted the Netflix talk show Chelsea (2016–2017); Author of multiple best-selling books.
• Known For: Her earthy, bawdy, and fearless style of comedy and commentary.

The Unexpected Origin of a Brief Celebrity Romance

The story of 50 Cent and Chelsea Handler began in the most professional of settings: a late-night talk show. The two first met when 50 Cent appeared as a guest on Handler’s popular E! show, Chelsea Lately, around 2009. The chemistry was immediately palpable, an electric mix of Handler’s sharp, often sarcastic humor and 50 Cent’s cool, unflappable demeanor.

Their brief romance officially took place in 2010 and early 2011. Despite the short duration, the relationship was highly publicized, largely due to the sheer novelty of the pairing. A platinum-selling rapper and a boundary-pushing comedian were an unlikely duo, and the media storm surrounding them was intense. Handler herself has frequently spoken about the relationship, often with a mix of fondness and humor, cementing its place in pop culture history.

The comedian has consistently referred to the rapper as a "sweetheart," a term that surprised many given 50 Cent's tough public persona. This perception of a softer, more charming side of the "In Da Club" artist is a recurring theme in Handler’s reflections on their time together. Her friends, she revealed, absolutely "loved" the relationship, finding 50 Cent to be a fun and engaging partner.

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The $200,000 Bentley and the "Favorite Ex" Status

The most recent and compelling details about their brief romance emerged during Handler's 2024 appearance on the popular *Call Her Daddy* podcast. During the interview, Handler didn't just label 50 Cent as her "favorite ex"—a title she has used before—but she also unveiled a truly outlandish anecdote demonstrating her efforts to impress the successful businessman.

The Bentley Purchase Revelation

Handler confessed that she bought a Bentley solely because 50 Cent owned one. The comedian, known for her candidness, admitted that she drove the luxury vehicle for only a short time before realizing the absurdity of the purchase, which was an attempt to match the rapper's extravagant lifestyle. The price tag for such a car can easily exceed $200,000, making it a costly, albeit hilarious, gesture in a short-lived relationship.

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50 Cent, whose real name is Curtis Jackson, was quick to respond to this revelation. In a typical fashion, the hip-hop mogul took to social media to comment on Handler's confession, confirming the story and humorously acknowledging the lengths she went to during their dating period. His response often maintains a light-hearted, appreciative tone, suggesting that the feeling of mutual respect, despite their past, is genuine.

Why He’s Her "Favorite Ex"

Beyond the expensive gifts and the sweet personality, Handler's fondness for 50 Cent stems from his genuine nature. She has praised him for being a "sweetheart" and a person who was always transparent. This level of complimentary commentary from a celebrity about an ex-partner, years after the breakup, is rare and speaks volumes about the quality of their connection, however brief it was.

From Flirting to Feuding: The Political Divide

While their personal history is marked by affection and humor, their public interactions have taken a sharp turn into contentious territory due to political differences. This is the most recent and relevant aspect of their relationship, proving that their connection, even as friends, is still active and occasionally volatile.

The 2020 and 2024 Endorsement Clashes

The most significant public clash occurred when 50 Cent appeared to endorse Donald Trump during the 2020 election cycle, primarily over concerns about proposed tax increases under the opposing candidate. Chelsea Handler, a vocal progressive and political activist, immediately and publicly called out her ex-boyfriend.

Handler’s reaction was swift and pointed. She took to social media, urging 50 Cent not to vote for Trump and even offering to pay his taxes if he reconsidered his stance. The comedian made it clear that while she still held affection for him, she strongly disagreed with his political position. This public disagreement highlighted the fundamental differences in their worldviews, showing that while they could connect romantically, their political ideologies were miles apart.

The political friction has carried over into the 2024/2025 election cycle, with the two continuing to have differing opinions on key issues, including 50 Cent’s comments on the RICO charges and the Black vote. Handler has consistently used her platform to challenge his political statements, often in a humorous but firm manner, ensuring that their dynamic remains a relevant topic in both entertainment and political news.

An Enduring, Complicated Friendship

Despite the public political sparring and the decade that has passed since their brief romance, the story of 50 Cent and Chelsea Handler is defined by an enduring, if complicated, friendship. They remain two of the most powerful and influential voices in their respective fields—hip-hop and comedy—and their shared history is a testament to the unpredictable nature of celebrity dating.

The fact that Handler continues to speak so highly of him, even calling him her "favorite ex," suggests a deep-seated respect. 50 Cent's playful and responsive commentary also indicates that the mutual admiration is not one-sided. Their relationship serves as a unique case study in Hollywood: a brief fling that has created a permanent, newsworthy bond, proving that sometimes, the most unexpected pairings make the most lasting impressions.