5 Shocking Revelations From Chelsea Handler On Dating 50 Cent: The Sweet, The Spicy, And The Political Feud

The relationship between comedian Chelsea Handler and rapper Curtis "50 Cent" Jackson remains one of Hollywood's most unlikely and intriguing celebrity pairings. Despite their brief romance lasting only a few months in the early 2010s, their interactions have continued to generate headlines, especially in recent years. As of the current date, December 13, 2025, Handler has offered new, candid insights into their connection, contrasting her fond memories of their dating life with their very public and explosive political disagreements.

Handler's latest revelations, particularly during a recent appearance on the *House Guest* podcast hosted by Scott Evans, paint a complex picture of their dynamic, moving from a surprisingly sweet, genuine connection to a fiery, public spat over the US political landscape. This article dives deep into the full story, from their initial meeting on her talk show to the present-day feud that proves their relationship, though short, was far from forgettable.

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

The pairing of a sharp-witted, liberal, late-night comedian with a tough, entrepreneurial hip-hop mogul was a media sensation. To understand their dynamic, it is essential to review the profiles of the two powerhouse personalities involved.

• The Untouchable Privacy 7 Secrets Of Rachel Mcadams And Jamie Lindens Life Beyond The Red Carpet E820e

Chelsea Handler: Comedian, Author, and Activist

• Full Name: Chelsea Joy Handler
• Born: February 25, 1975 (Livingston, New Jersey)
• Occupation: Stand-up Comedian, Actress, Writer, Television Host, Producer, Activist.
• Notable Works: Host of *Chelsea Lately* (2007–2014) on E!, host of *Chelsea* (2016–2017) on Netflix.
• Books: *My Horizontal Life: A Collection of One-Night Stands*, *Are You There, Vodka? It's Me, Chelsea*, *Chelsea Chelsea Bang Bang*, *Lies That Chelsea Handler Told Me*, and *Life Will Be the Death of Me*.
• Public Persona: Known for her earthy, bawdy, and unfiltered style, and her strong, outspoken political views.

Curtis "50 Cent" Jackson: Rapper, Actor, and Mogul

• Full Name: Curtis James Jackson III
• Born: July 6, 1975 (Queens, New York)
• Occupation: Rapper, Actor, Television Producer, Entrepreneur.
• Musical Debut: Rose to international fame with his 2003 debut album, *Get Rich or Die Tryin'*.
• Television Success: Executive Producer of the highly successful *Power* universe franchise, including *Power Book II: Ghost* and *Power Book III: Raising Kanan*.
• Business Ventures: Has built an extensive empire in music, film, television, and various business ventures, solidifying his status as a media mogul.
• Public Persona: Known for his street-smart lyricism, business acumen, and controversial, often provocative social media presence.

The Sweetest Surprise: Handler’s Candid Relationship Recall

The story of Chelsea Handler and 50 Cent’s romance began in 2009 when the rapper appeared as a guest on her late-night talk show, *Chelsea Lately*. This initial, seemingly professional interaction quickly sparked a brief but intense relationship in the early 2010s.

"He Convinced Me to Date Him"

In her recent interview on the *House Guest* podcast with Scott Evans, Handler detailed how the relationship started. She revealed that 50 Cent was persistent, essentially convincing her to go out with him after his appearance on her show. She recalled inviting him to her stand-up performance in New Orleans, after which they planned to meet for a drink. The story continued with him checking into her hotel, a move that Handler recounted with her signature blend of humor and candidness.

"One of the Sweetest People"

Perhaps the most surprising revelation from Handler’s recent reflection is her description of 50 Cent’s character during their time together. Despite his tough public image and the couple's odd-couple status, Handler insisted that he was genuinely kind. She stated that 50 Cent was "one of the sweetest people" she had ever dated. This sentiment counters the typical narrative surrounding the rapper and highlights a soft side of the mogul that few get to see.

• 7 Shocking Things Jessica Capshaw Revealed About Growing Up With Steven Spielberg As Her Stepfather 892ho

The "Biggest Disappointment"

While the relationship was sweet, Handler also admitted to one "biggest disappointment" of dating the rapper. In one of her earlier interviews, she had mentioned that the relationship ended because of external pressure and the difficulty of merging their two very different worlds. However, her recent comments on his character focus on the positive, confirming that the foundation of their connection was built on genuine affection, not just a publicity stunt.

The Political Firestorm: From Romance to Rivalry

While their romantic history is a source of nostalgic reflection for Handler, their most recent public interactions have been far less amicable. Their fundamentally different political views led to a fiery, highly publicized feud that erupted over social media and television appearances.

The Trump Endorsement and RICO Charges

The renewed rivalry began when 50 Cent publicly expressed support for Donald Trump, specifically claiming that many Black men would vote for the former president due to issues like the use of RICO charges. This statement immediately drew the ire of the staunchly liberal Handler, who was quick to blast her ex-boyfriend publicly.

• The Surprise Vegas Wedding And Shared Grief 5 Shocking Details Of John Schneider And Dee Dee Sorvinos Whirlwind Romance Ohirf

Handler’s Public Retort and Offer

Handler did not mince words, famously taking to social media and television to criticize his political position. In a controversial comment, she suggested that 50 Cent "can't vote Trump because he's a Black person," indicating her belief that his political choice was a betrayal of his identity and community. She also made a headline-grabbing offer: she would pay his taxes if he agreed to stop endorsing Donald Trump for re-election. The offer, though likely facetious, highlighted the severity of her disapproval.

50 Cent’s "Gator" Response

50 Cent, never one to back down from a public spat, responded to Handler’s comments with his characteristic blend of humor and bluntness. He took to social media, referencing their past relationship with a playful yet firm message. "I love ya Gator, don't let Trump and Joe Biden come between us girl," he wrote, acknowledging the feud while attempting to inject some levity and nostalgia into the situation. This response confirmed that despite the political chasm, a residual level of familiarity and perhaps even affection remains between the two stars.

The Lasting Legacy of an Unlikely Couple

The ongoing public dialogue between Chelsea Handler and 50 Cent proves that their brief time together has a lasting legacy. It is a relationship that continues to provide fresh content and discussion points years after it ended. Their story is a compelling example of how celebrity relationships, even short-lived ones, can evolve into complex, multi-layered narratives.

From Handler’s recent, surprisingly sweet reflections on the *House Guest* podcast—where she praised his character—to their recent, explosive political clash over the 2024 US election cycle, the Handler-50 Cent dynamic is a case study in contrasting public and private personas. It shows that while personal affection can be genuine, deeply held political and social beliefs can create an unbridgeable divide, even between people who once shared a sweet, intimate connection.

Ultimately, the "Chelsea Handler 50 Cent interview" is not just one event, but a continuous series of public and private reflections that keep their unique, decade-old relationship relevant. It’s a story of two powerful personalities who, despite their differences, continue to find ways to engage, whether in romance or rivalry.