50 Cent Celebrates Diddy’s Prison Sentence with Characteristic Humor
Curtis “50 Cent” Jackson has never been one to miss an opportunity for a well-timed jab, especially when it comes to his longtime rival Sean “Diddy” Combs. Following Combs’ sentencing to 50 months in prison, Jackson took to social media with his trademark humor, effectively dancing on the grave of Diddy’s freedom. “Hey to whoever was booking Diddy for speaking engagement. I heard he won’t be able to make it,” the Queens rapper posted on X, complete with a shrug emoji before adding, “I’m available!” accompanied by a laughing emoji. The post included a court sketch of Combs alongside a cropped headshot of his lawyer Marc Agnifilo, highlighting the gravity of the situation while simultaneously mocking it. The jab was particularly pointed as it referenced Combs’ overconfident booking of speaking engagements in Miami for the upcoming week—engagements he had scheduled with the misplaced optimism that he would be released on time served.
This wasn’t 50 Cent’s only celebration of Diddy’s downfall. The day before the sentencing, he posted an extended message on social media addressed to the judge overseeing Combs’ case. “I have had an ongoing dispute with Puffy for over 20 years. He is very dangerous. Multiple times I have feared for my life,” wrote the rapper, who famously survived being shot nine times in 2000. After beginning with what appeared to be serious warnings, the “Many Men” artist couldn’t resist ending with a comedic punch: “Anyway, Diddy’s only going to return to hiring more male sex workers and keeping most of the baby oil away from the general public. And babies need it!” The joke, crude as it may be, reflects the unfiltered personality that has made 50 Cent both beloved by fans and a formidable presence in the hip-hop community.
The feud between these two hip-hop moguls has deep roots, dating back to at least 2005. Their rivalry has been well-documented in the music world, with 50 Cent even releasing “The Bomb,” a diss track specifically targeting Diddy. In that 2007 track, he quipped, “I guess this means I won’t be invited to the white parties in the Hamptons!”—a reference to Combs’ famous lavish all-white attire parties that were once a staple of celebrity culture. This long-standing tension between the two artists has played out publicly for nearly two decades, with 50 Cent often positioning himself as the antagonist to Diddy’s more polished public image.
What makes this particular round of trolling notable is its timing—it comes at perhaps the lowest point in Combs’ public life and career. The once-revered music mogul, who built an empire spanning music, fashion, and liquor, now faces years behind bars, his reputation in tatters. 50 Cent, who has often positioned himself as an underdog despite his own massive success, seems to find particular satisfaction in watching the fall of someone who represented the establishment of hip-hop royalty. His social media victory lap speaks to the personal nature of their feud and suggests that for 50 Cent, this moment represents vindication of sorts.
While some might view 50 Cent’s comments as harsh or opportunistic, they’re entirely in character for the rapper who has built much of his brand on unfiltered authenticity and a willingness to speak his mind regardless of consequences. Throughout his career, 50 Cent has navigated his own controversies while maintaining relevance not just as a musician but as a successful businessman and television producer. His evolution from street rapper to entertainment mogul has been remarkable, yet he has never lost the edge that first made him famous—an ability to cut through pretense with humor, even when that humor might be considered inappropriate by some.
This latest chapter in the 50 Cent-Diddy saga highlights how hip-hop rivalries can span decades, evolving beyond music into personal vendettas that play out in the public arena. In many ways, 50 Cent’s response to Diddy’s sentencing reflects the culture of hip-hop itself—competitive, unapologetic, and often brutally honest. As Combs begins his prison sentence, 50 Cent’s trolling serves as a reminder of how dramatically fortunes can change in the entertainment industry. Where once Diddy represented the pinnacle of hip-hop success and 50 Cent was the upstart challenger, their positions have now dramatically reversed—with one man celebrating his freedom and success while the other faces years of confinement. In the unpredictable world of hip-hop, perhaps the only certainty is that 50 Cent will continue to have something to say about it, likely with his signature combination of humor and ruthlessness.
