The Unlikely Exes: 5 Shocking Ways Chelsea Handler And 50 Cent's Relationship Still Makes Headlines In 2025

The enduring, yet unlikely, connection between comedian Chelsea Handler and hip-hop mogul 50 Cent continues to capture public attention, proving that some Hollywood romances never truly fade. While their brief relationship dates back over a decade to 2011, the pair have consistently resurfaced in headlines, most recently due to Handler's candid reflections on their time together and a high-profile political clash that went viral. As of late 2025, their dynamic remains a fascinating blend of mutual respect, comedic fodder, and sharp political opposition, making them one of the most talked-about ex-couples in the entertainment industry. The story of the outspoken comedian and the G-Unit powerhouse began on the set of her former E! talk show, *Chelsea Lately*, and has evolved into a complex, modern friendship punctuated by public commentary and social media sparring. The comedian has recently (in 2023 and 2024) dubbed the rapper her "favorite ex," even as their political views clashed dramatically over the past few years, highlighting a unique bond that transcends typical celebrity breakups.

Chelsea Handler and 50 Cent: A Quick Dual Biography Profile

Despite their different career paths—one in stand-up comedy and television, the other in music and executive production—Chelsea Handler and Curtis "50 Cent" Jackson share a surprising number of professional and personal milestones that led to their brief but memorable romance.

Chelsea Handler (Chelsea Joy Handler)

• Born: February 25, 1975, in Livingston, New Jersey, U.S.
• Profession: Stand-up Comedian, Actress, Writer, Television Host, Producer, Activist.
• Notable Works: Host of *Chelsea Lately* (2007–2014) on E!, host of the Netflix talk show *Chelsea* (2016–2017), New York Times best-selling author of several books including *Are You There, Vodka? It's Me, Chelsea*.
• Recent Projects: Critically acclaimed Netflix stand-up specials *Revolution* (2022) and *The Feeling* (2024), which addresses her life and sobriety journey.

50 Cent (Curtis James Jackson III)

• Born: July 6, 1975, in Queens, New York, U.S.
• Profession: Rapper, Songwriter, Actor, Television Producer, Entrepreneur.
• Notable Works: Debut album *Get Rich or Die Tryin'* (2003), founder of G-Unit, and executive producer of the massively successful Starz crime drama series *Power* and its multiple spin-offs.
• Business Ventures: Music (G-Unit Records), Film/TV (G-Unit Films and Television), and various other ventures, cementing his status as a major entertainment mogul.

The Unexpected 2011 Romance: Sweetness and Sobriety

The relationship between the two stars began in 2011 after 50 Cent appeared on *Chelsea Lately*. Handler has frequently reflected on this period, always speaking highly of the rapper's character, which often surprises her fans given their contrasting public personas. She has consistently referred to the "In Da Club" artist as one of the "sweetest people" she has ever dated, a comment she reiterated in recent interviews. She recalled how he "convinced" her to date him, and that her friends particularly enjoyed his company, often telling her how much they loved hanging out with him. This mutual affection, even years later, suggests the bond was genuine, albeit brief. However, Handler also revealed what she jokingly referred to as the "biggest disappointment" of their time together: his lifestyle. In a classic Handler comedic twist, she noted that 50 Cent is completely sober and doesn't do drugs. This revelation humorously contrasted with her own well-documented history of enjoying a drink, a detail that perfectly encapsulates the odd-couple nature of their short-lived romance.

The Explosive Political Feud That Went Viral

Despite their friendly post-breakup status, the pair's relationship hit a highly public snag in 2020 during the U.S. presidential election, a disagreement that continues to define their public interactions. The clash began when the *Power* executive producer publicly endorsed Donald Trump, citing potential tax hikes under Joe Biden's proposed policies. Handler, a vocal and dedicated Democrat, immediately took to social media to "scold" her former flame. She publicly offered to pay his taxes if he would reconsider his political stance, stating, "I love ya Gator, don't let Trump and Joe Biden come between us girl." The heated exchange quickly went viral, pitting the two celebrities against each other over one of the most divisive political landscapes in recent memory. While the moment was tense, it ultimately ended with a light-hearted, yet firm, response from 50 Cent, who told her not to let politics ruin their friendship. The incident became a prime example of how celebrity relationships, even old ones, can be tested by political polarization.

The "Favorite Ex" Status and NSFW Stand-Up

In the years following the political clash, Handler has solidified 50 Cent's place in her personal history as her "favorite ex," a title she frequently mentions in interviews and her stand-up comedy routines. This public declaration of affection, even with a political chasm between them, keeps their story relevant and engaging for fans. Handler’s comedy, known for its raw and explicit nature, often includes anecdotes about her dating life. In one of her recent stand-up specials, she made a particularly NSFW (Not Safe For Work) comment about the rapper. Rather than taking offense, 50 Cent reacted to the mention on social media, posting a screenshot of the comment and adding his own humorous—and slightly bewildered—response. This interaction, which occurred over a decade after they dated, highlights their unique, playful, and adult dynamic. It confirms that the G-Unit mogul is fully aware of his former girlfriend's comedic use of their past, and he seems to take it in stride.

Why the Chelsea-50 Cent Dynamic Endures in 2025

The continued public interest in Chelsea Handler and 50 Cent in late 2025 is a testament to their enduring chemistry and the fascinating contrast of their worlds. Their story is a perfect storm of LSI (Latent Semantic Indexing) entities and topics that feed the news cycle:

• The Odd Couple Trope: The juxtaposition of the foul-mouthed, liberal comedian and the street-smart, conservative-leaning hip-hop mogul is inherently compelling.
• Political Polarization: Their highly public disagreement over Donald Trump and Joe Biden serves as a microcosm of the current national political divide.
• The "Favorite Ex" Narrative: Handler's consistent, positive reflections on 50 Cent, despite the political differences, provides a rare, heartwarming element of mutual respect in a typically cynical industry.
• Career Longevity: Both have remained highly relevant, with 50 Cent's ongoing success as an executive producer of the *Power* universe and Handler's new Netflix specials like *The Feeling* and her ongoing advocacy work.

Ultimately, the Chelsea Handler and 50 Cent saga is a modern celebrity tale. It’s a story not of a lasting romance, but of a lasting, albeit complicated, friendship that proves that two people from vastly different worlds can connect, clash, and still hold a special place for each other in the public eye. Their ability to turn a brief relationship into a decade-plus of engaging, headline-worthy content ensures that the story of the comedian and the mogul will continue to be discussed for years to come.

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