50 Cent's Ex Chelsea Handler Once Took Him To Task For His Support Of Donald Trump

Of all the men scattered across Chelsea Hander's dating history, 50 Cent was a standout. The former couple reportedly met when the "Candy Shop" hitmaker appeared on Handler's eponymous talk show. Based on this TikTok clip of their chat, it was obvious they were attracted to each other and weren't afraid to make their feelings known by flirting openly. During a 2013 appearance on "The Oprah Show," the comedian revealed that the rapper sent her flowers afterwards, but Handler wasn't sure whether she wanted to get into a relationship with him. However, 50 Cent completely won her over when he visited New Orleans to see her. Handler had nothing but great things to say about her ex. "His persona is completely antithetical to who he is in real life," she gushed. "He's a sweetheart and he's, like, so cute, and you just want to like [...] hang from his neck. [He's] so big and beefy." 

Despite all that high praise, though, Handler acknowledged that their 2011 romance was short-lived and casual, but she still had a great time nonetheless. Nearly a decade after Handler and 50 Cent's relationship ended, the two had a somewhat testy public interaction on X, formerly known as Twitter. In October 2020, the rapper seemingly tweeted his support for Donald Trump in the upcoming presidential election because he wasn't a huge fan of Joe Biden's taxation plans. The comedian responded to the tweet by writing, "You used to be my favorite ex-boyfriend." Then, she seemingly swayed the "In Da Club" rapper's opinion in a different direction with a rather interesting proposal. 

During her October 2020 appearance on "The Tonight Show Starring Jimmy Fallon," Chelsea Handler touched on her feelings about her former partner supporting Donald Trump. The comedian reasoned that her ex was misinformed about Joe Biden's taxation policies, asserting, "I had to remind him that he was a Black person, so he can't vote for Donald Trump, and that he shouldn't be influencing an entire swathe of people who may listen to him because he's worried about his own personal pocketbook," (via YouTube). After she admitted that 50 Cent hadn't responded to her plea, Handler made a statement that might have been of more interest to him: "I am willing to, you know, seal the deal in more ways than one if he changes his mind and publicly denounces Donald Trump." 

She also hinted that she would be willing to get back together with the Grammy-winning rapper if he made those changes. 50 Cent subsequently took to X to share a clip of the interview. After seemingly expressing his happiness at the idea of having the comedian back in his life, the "In da Club" hitmaker condemned Trump and jokingly accused him of committing several crimes. A few days after the tweet was posted, Handler appeared on "The View," and confirmed that she had reached out to her ex privately to find out whether he was truly backing Trump. They had a 30-minute phone call, during which 50 Cent clarified that his initial tweet supporting the former "Apprentice" host was meant in jest and he was planning to vote for Joe Biden. 

Elsewhere in Chelsea Handler's interview on "The View," she joked about offering to pay 50 Cent's taxes to ease his mind about supporting Joe Biden in the 2020 presidential election (the talk show host noted that she couldn't actually cover them because that would be tantamount to Handler illegally paying the rapper to vote for a presidential candidate). She also coyly suggested that she had offered to compensate her ex-boyfriend in a different way too. However, it didn't seem like the two ever rekindled their romance. Then, in 2024, 50 Cent made a strange remark about Donald Trump seemingly out of nowhere. When a CBS News interviewer at Capitol Hill asked him how African-American men could sway the 2024 elections, the "P.I.M.P." hitmaker responded, "I see them identifying with Trump because they got RICO charges." He was apparently alluding to the presidential hopeful's RICO charges for his election interference case. 

Notably, 50 Cent confessed that he was unsure about who he was voting for this time around. Despite everything, Handler's earlier conversations with the Grammy winner weren't in vain because they arguably helped the comedian accomplish her goal of getting people talking about Trump for all the right reasons. As Handler argued to Variety in 2016, the bright side of the politician's presidential run was that, "It's kind of great to have a person like that represent everything that's wrong in the world." She continued, "It's always a good thing to look at somebody and say, 'That's the worst thing that could happen.' I think we should keep [Trump] in the spotlight — not as president, obviously."