Why does 50 Cent always troll Diddy?

50 Cent is renowned for trolling, and his relentless goading isn’t just reserved for Diddy. However, over the years, his scorn for the Bad Boy founder has grown, and since the allegations made against the mogul last year, Fifty has been unrelenting in his attacks.

This wasn’t always the case, but for the best part of two decades, 50 Cent and Diddy have been at odds, and sometimes, it makes for uncomfortable viewing. Whether it’s the subtle digs made by Fifty on social media and podcasts or the awkward silence from Diddy, there has always been something off about their exchanges.

Although 50 Cent would never have stopped taking potshots at the Press Play creator, the allegations of sexual misconduct, the barrage of lawsuits and the CCTV footage of him abusing his ex-girlfriend, Cassie Ventura, have added gallons of fuel to a fire that was already out of control.

The two clubs with which Fifty has beaten Diddy over the years concern his shady business practices and one big question mark over his sexuality. Although the latter is seen as more distasteful, for a long time, Diddy has had to fight the narrative put out there by 50 Cent and kept alive with industry hearsay.

To the oblivious, it would appear that 50 Cent hates Diddy. However, there is far more behind this strange predicament, and it gets relatively murky.

Following Biggie Smalls’ death in 1997, Bad Boy Entertainment was looking for a new star, and at the turn of the millennium, Diddy met with 50 Cent to review a record deal. However, the deal fell through, and Fifty proactively chose to sign with Eminem’s Shady Records under Interscope and began work on his debut album,Get Rich Or Die Tryin’.

Although this seems like a minor detail, as a New Yorker who was in the streets during the time of Biggie Smalls’ death, Fifty has repeatedly asserted that he personally knows that Diddy was part of the murder. Even though he can’t prove it, in 2006, long before the rise of X (formerly Twitter), 50 Cent released a diss track aimed at Diddy addressing just this.

50 Cent - Diddy - Split - Hip Hop Hero
Credit: Hip Hop Hero / YouTube Stills

On the song entitled ‘The Bomb’, the Queens musician raps lyrics such as “Who shot Biggie Smalls? We don’t get ’em / They gonna kill us all.” He continues, “Man, Puffy know who hit that n*gga.”

Fifty then goes into a rant and exclaims, “Oh, I guess this means I won’t be invited to the white parties in the Hamptons. I don’t give a fuck! I don’t wanna hang out with your punk ass, no way.” He then insinuates that Diddy’s ex-girlfriend, Misa Hylton, said something to him off the record, screaming, “Why you want to make me tell everybody what Misa told me?!”

From this 2006 track alone, it is evident that 50 Cent was aware of the infamous Diddy parties even in the early 2000s, and he has been vocal about them ever since. This is most likely the source of tension between 50 Cent and the Bad Boy Founder.

Since the 2010s, 50 Cent has been calling Diddy all sorts of names and has repeatedly claimed that Diddy is “fruity”. During an appearance on the Drink Champs podcast with Noreaga and DJ EFN, Fifty recalled an exchange the ‘Last Night’ rapper had with Fabulous, recounting, “When he says things, he doesn’t even know what he’s saying is, like, fruity. He [once said] to Fabulous, ‘Me and you, we need to party!'”

He continued, “[Diddy] said something to me a long time ago at Chris Lighty’s wedding. He told me he’d take me shopping. I looked at him like, ‘What’d you just say? Let me move, man, before I do something. You gon’ make me mess up the wedding.’ No. That’s something a guy says to a girl.”

Although 50 Cent and Diddy both began their careers in hip-hop and transitioned to mogul status through television and Hollywood, Fifty has always been the antagoniser who views the other’s success as illegitimate. In 2018, during an appearance on The Breakfast Club, Diddy claimed that he and Cent had no conflict, stating “When he does that, it’s like funny to me. I don’t really take it personal.”

He added, “I know he has a different sense of humour, and he’s just not in my life. We don’t have to never cross paths, and I will never say anything negative about him, you know, because that’s just not me.” Unfortunately, as more and more is unearthed about Diddy and his sex trafficking charges, it is already beginning to look like a lot of what 50 Cent said is coming to pass.

You can hear a timeline of Diddy and 50 Cent’s strange relationship in the video below.