5 Shocking Truths About Chelsea Handler And 50 Cent’s Relationship: The Real Reason They Broke Up And Her ‘Biggest Disappointment’

Despite their short-lived romance over a decade ago, the public fascination with the relationship between comedian Chelsea Handler and hip-hop mogul 50 Cent (Curtis Jackson) remains as strong as ever. As of December 2025, Handler continues to speak candidly about the rapper, consistently labeling him her "favorite ex-boyfriend" and a "sweetheart," proving their connection was anything but ordinary. Their unlikely pairing captivated the media, blending the worlds of sharp-tongued late-night comedy and gritty, successful rap, creating a narrative that still generates headlines today.

Their brief, whirlwind courtship in the early 2010s was a cultural moment, but Handler’s recent reflections offer a fresh, unique perspective on their time together, revealing the surprising details behind how the *Get Rich or Die Tryin’* artist convinced her to date him, the unexpected challenges of their interracial romance, and the one thing about him that she jokingly called her "biggest disappointment."

The Unexpected Power Couple: Chelsea Handler and Curtis Jackson Biography

The pairing of a platinum-selling rapper and a boundary-pushing comedian seemed like a publicity stunt, yet their mutual respect and chemistry were undeniable. Here is a brief look at the two formidable stars who came together:

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• Chelsea Handler (Comedian, Author, Host)
  • Born: February 25, 1975 (Age 50 as of 2025)
  • Hometown: Livingston, New Jersey, U.S.
  • Career Highlights: Host of the E! late-night talk show *Chelsea Lately* (2007–2014); host of *Chelsea* on Netflix (2016–2017); multiple best-selling books including *Are You There, Vodka? It's Me, Chelsea*; Grammy nominee for Best Comedy Album (*Evolution*).
  • Notable Relationships: Ted Harbert, Jo Koy, 50 Cent (Curtis Jackson).
  • Public Persona: Known for her fearless, often raunchy, and politically charged humor.
• 50 Cent (Curtis Jackson) (Rapper, Actor, Producer)
  • Born: July 6, 1975 (Age 50 as of 2025)
  • Hometown: South Jamaica, Queens, New York, U.S.
  • Career Highlights: Global success with albums *Get Rich or Die Tryin’* and *The Massacre*; founder of G-Unit Records; executive producer and star of the highly successful *Power* universe franchise on Starz; multiple Grammy Awards and a Primetime Emmy Award.
  • Notable Relationships: Shaniqua Tompkins, Daphne Joy, Chelsea Handler.
  • Public Persona: Known for his business acumen, social media trolling, and transition from music to television mogul.

How the Romance Started: A Backstage Connection on 'Chelsea Lately'

Their story began not in a glamorous club, but on the set of Handler's former E! talk show, *Chelsea Lately*. The rapper, then known primarily for his music, appeared as a guest in 2009, and the connection was immediate, sparking an *unlikely celebrity romance* that would soon dominate entertainment headlines.

Handler has often recounted the charming and persistent way 50 Cent pursued her. In a 2023 interview, she revealed that the G-Unit mogul essentially "convinced" her to go on a date. He was persistent, sending her flowers and making a concerted effort to win her over, a detail that surprised many who only knew his tough, public persona.

The comedian admitted that she was initially hesitant, believing the whole situation was "ridiculous." However, his genuine nature and "sweet" demeanor quickly won her over. This behind-the-scenes courtship highlights a side of 50 Cent that few get to see, contrasting sharply with his often-controversial online presence.

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Their relationship, though brief—lasting only a few months—was intense and memorable. Handler has repeatedly praised him, saying, "I love 50 Cent, he was fun. He was just a sweetheart and he was fun to be around." This consistent praise cemented his status as her "favorite ex."

The Surprising Reason for the Split and Her ‘Biggest Disappointment’

The end of their relationship was not marked by a major public drama, but rather a mutual fizzling out, often attributed to their demanding schedules and the complexities of dating in the spotlight. However, Handler’s recent revelations have provided more specific, and humorous, details about what she considered the one true letdown of their time together.

Truth #1: The Split Was Due to Schedule, Not Conflict

While the media speculated on a dramatic fallout, the reality was more mundane. The relationship ended because of the logistical challenges of their high-profile careers. Both were at the peak of their fame—Handler with her nightly talk show and 50 Cent balancing music, acting, and his burgeoning business empire. This classic celebrity problem of an *impossible schedule* ultimately proved too much for the budding romance.

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Truth #2: Handler’s Joking ‘Biggest Disappointment’

In a candid interview, Handler revealed the one thing that truly disappointed her about the rapper, delivered with her signature comedic timing. She joked that the "biggest disappointment" of dating 50 Cent was his lifestyle. "He's a very sweet guy and he doesn't do drugs, which was the biggest disappointment of all," she quipped. This self-deprecating joke highlights the contrast between the rapper's tough public image and his surprisingly clean-cut private life, a detail that provided a fresh layer of insight into their dynamic.

Truth #3: The Shocking Interracial Backlash

Handler also spoke candidly about the negative public reaction to their *interracial celebrity romance*. She recalled that the backlash was surprisingly harsh and often "racist," a detail that she felt compelled to address years later. This experience highlighted the societal challenges they faced that went beyond typical celebrity gossip, adding a serious dimension to their story.

From Lovers to Political Adversaries: The 2020 Feud That Resurfaced Their Connection

While their romantic relationship ended over a decade ago, Handler and 50 Cent briefly reignited their public connection—and controversy—in 2020 over a political disagreement that went viral. This event is a critical part of their shared narrative, showcasing how their strong personalities clash on major issues.

Truth #4: The Trump Tax Scare

The feud began when 50 Cent publicly voiced support for then-President Donald Trump, citing concerns over Joe Biden's proposed tax plan, which he feared would heavily impact high-earners like himself. His post on social media caused an immediate stir, especially among his progressive-leaning fans and, most notably, his former flame.

Truth #5: Handler's Controversial Call-Out

Chelsea Handler did not hold back. She publicly called out 50 Cent, offering to pay his taxes if he reconsidered his political stance, but her comments went further. In a controversial moment that drew significant criticism, Handler stated: "I had to remind him that he was a black person, so he can't vote for Donald Trump." This remark led to a media firestorm, with many accusing Handler of being racially insensitive or attempting to dictate the Black vote.

50 Cent’s response, however, was classic G-Unit charm mixed with playful defiance. He publicly backed down from his support for Trump, but not before sending a lighthearted message to Handler: "I love ya Gator, don't let Trump and Joe Biden come between us girl." This playful exchange demonstrated that despite their political differences and the public drama, a deep-seated affection and respect—or at least a very good friendship—still existed between the two stars.

The Enduring Legacy of Chelsea and 50 Cent

The story of Chelsea Handler and 50 Cent remains one of Hollywood’s most fascinating and enduring celebrity pairings. It was a relationship built on mutual humor and unexpected sweetness, transcending the boundaries of their respective worlds. Handler’s consistent, positive reflections—calling him her "favorite ex" and a "sweet guy"—ensure that the *Chelsea Handler 50 Cent relationship* will continue to be a topic of discussion for years to come.

Their ability to move past a brief romance, navigate a public political feud, and still maintain a playful, respectful connection is a testament to the genuine bond they forged. It serves as a rare example of a celebrity ex-couple who truly appreciate each other, even when they are on opposite sides of the political spectrum.