If you’ve been tuned in to hip hop news in the last few months, you’re likely well acquainted with the situation surrounding rapper and music mogul Sean “Diddy” Combs, who is currently incarcerated while awaiting trial on federal charges of sex trafficking and racketeering. While the news of his arrest shocked many, some major hip hop heads were largely unfazed, as the writing has been on the wall regarding Diddy’s alleged behavior for years now. Primarily, those who follow rapper and notorious troll 50 Cent were tuned in to tales of Diddy’s bizarre dealings dating back decades. The “I Get Money” lyricist has been extremely flagrant about his characterization of Diddy as a twisted individual, sparking an on-again off-again feud extending across generational lines. 50 has even partnered with Netflix to launch a Diddy documentary (tentatively titled Diddy Do It), outlining the mogul’s criminal history and arrest.

To get a full understanding of 50 Cent and Diddy’s contentious relationship, we’ll have to construct a rough timeline of their business and performance partnerships, shared tracks and public comments. The New York natives have a decades-long history as peers in the rap game, meaning there’s a lot of ground to cover. So, let’s travel back to the late 1990s, when Diddy was on top of the rap landscape and 50 Cent was still a relative up-and-comer. With any luck, this shared history will paint a simple and compelling picture of why Fif has been perhaps the most consistent anti-Diddy voice in the hip hop world.

Shots Were First Fired in 1999

Those who have followed 50 Cent’s music career know that the rapper-turned-television producer has always been a master at viral marketing. His very first single, “How To Rob,” was released in August 1999, name-checking a variety of popular artists in a humorously disrespectful way. These artists included 50’s own friends and collaborators, as well as established legends in rap like Jay-Z, DMX, the Wu-Tang Clan and of course, Diddy. While the latter never responded to 50 Cent’s lyrics directly, most of his peers took the lighthearted jabs in stride. Still, things continued to sour between the pair shortly after 50 Cent was shot in May of 2000. 50’s shooting incident led to him losing his distribution deal with Columbia Records, and ultimately being blackballed in the music industry for several years.

Though the shooting can be traced back to Fif’s personal feuds with his peers in the criminal underworld of New York, nobody truly knows the exact nature of why he was blackballed from the industry. Depending on who you believe, some people say that 50 Cent’s outspoken lyrics on tracks such as “Ghetto Qur’an (Forgive Me)” made him too volatile as a commodity to the label. Others suggest that music industry heads such as Diddy were made to silence 50 Cent as a personal favor to his connections in New York’s gangland. Specifically, a former gang-banger turned executive by the name of Jimmy Henchman has been highlighted as a connection between the pair. Henchman, who is currently serving a life sentence in prison for drug trafficking, money laundering, witness tampering and a murder-for-hire plot involving 50 Cent affiliate Lodi Mack, was a known associate of Diddy’s when 50 was shot.

Diddy and 50 Cent Collaborated in the Early 2000s

Though some industry insiders claim that Diddy was involved in blackballing 50 Cent after the shooting, the situation seemed to be water under the bridge once the latter inked a million-dollar deal with Eminem’s Shady Records in 2002. The following year, 50 dropped his long-awaited debut album Get Rich Or Die Tryin’, catapulting him to superstardom. Later that year, Diddy even presented 50 with his MTV award after he won Best Rap Video for “In Da Club.” Whether Diddy had a hand in 50’s industry troubles or not, the rising star didn’t hold any animosity, as he agreed to pen several songs for the Bad Boy mogul, and even collaborated on tracks such as “Victory 2004,” “I Get Money (Forbes 1, 2, 3 Remix),” and The Notorious B.I.G.’s “Realest N****s.”

Despite their collaborative efforts, 50 Cent’s relationship with Diddy turned sour once more in 2006, when the “Many Men” rapper expressed interest in signing Mase to his newly minted G-Unit Records imprint. At the time, Mase was signed to Bad Boy Records, though he was experiencing label drama with Diddy, preventing him from releasing solo music. 50 Cent apparently reached out to Diddy with an offer to buy Mase out of his contract, and Diddy responded with an outlandishly high figure of $2 million. In response, 50 Cent put his grievances with Diddy on wax, dissing him with a barrage of attacks on the song “Hip Hop,” and even accusing him of pulling the strings behind The Notorious B.I.G.’s shooting death in 1997.

In “Hip Hop,” 50 raps “Who shot Biggie Smalls? We don’t get ’em they gon’ kill us all. Man Puffy know who hit that n**** man that n**** soft.” On the song’s outro, 50 continues to taunt and berate Diddy, stating, “Oh I guess this means I won’t be invited to the white parties in the Hamptons. I don’t give a f***. I don’t wanna hang out with yo’ punk ass no way… Don’t wanna make the deal n****, man I’ll f*** your s*** up n****.”

50 Cent Takes the Feud to Radio Shows and Social Media

Even if you’ve never been a big fan of 50 Cent’s music, you’ve surely seen him make headlines with his hilarious social media posts and interview appearances. Just as 50 has done in the past with the likes of Rick Ross and Ja Rule, he continued to tear down Diddy on public forums as often as he could throughout the early 2010s. Through appearances on Jam’n 94.5, Funkmaster Flex, The Breakfast Club and many more, 50 Cent would humorously trash Diddy’s music, business dealings, industry relationships and even attack his sexuality. Famously, Fif claimed that Diddy would offer to take all of his new male acquaintances on a shopping spree and buy them new clothes. The rapper viewed this offer as something of a sexual dog whistle, implying that Diddy may have had ulterior motives with the young men entering the music industry.

As the Power co-creator became more present in social media spaces such as Instagram and Twitter, he would continue to expand his Diddy smear campaign with endless memes and captions designed to antagonize the Bad Boy mogul at every turn. Over the years, 50 Cent has shared various conspiracy theories indicating Diddy’s alleged involvement in the murders of both Biggie and Tupac Shakur, and even launched a petition demanding that Diddy never use Biggie’s name on a record ever again. The petition received over 1,000 signatures from social media users. Furthermore, 50 frequently claimed that Diddy would take sexually explicit photos and videos of young men and women who attended his private parties and share them around in hip hop circles. Many of these claims have received increased scrutiny in recent months as Diddy’s impending trial looms.

50 Cent and Diddy Engage in the Vodka Wars

Right when the general public thought that 50 Cent would run out of material to smear Diddy with, both artists entered into the spirits business. Diddy’s ownership stake in Cîroc Vodka and 50’s partnership with Effen Vodka made them rivals in yet another industry, presenting 50 with a myriad of opportunities to troll his peer online. During the mid-2010s, Fif routinely posted doctored photographs of Diddy on social media with humorous captions trashing his Cîroc beverage brand. He would eventually triple down on this campaign by retweeting posts from other rappers painting them in a negative light, often blaming their missteps on the consumption of what he called “Puffy Juice.”

One of the most hilarious exchanges between Diddy and 50 Cent was wrought from their mutual attempts to troll one another with their respective vodka brands. Diddy apparently gifted 50 Cent a lifetime supply of Cîroc on the latter’s birthday in 2015, calling his brand “the superior ultra-premium” beverage. Fif responded a month later by sending a case of Effen to The Breakfast Club ahead of a Diddy interview, ensuring that it would be prominently displayed in the background. This caused one of Diddy’s employees to slyly crawl across the floor during the interview in an attempt to surreptitiously remove the bottle. Unfortunately for Diddy, this interaction caused a bit of a scene, playing right into 50’s hand and resulting in a host of jokes and memes online.

Fif’s Prophetic Wisdom Unfolds in the 2020s

Most hip hop heads likely saw 50 Cent’s constant harassment of Diddy over the years as little more than friendly banter. Though the pair occasionally exchanged harsh words, their relationship mostly seemed to consist of friendly jabs. Still, Diddy’s downfall saw the viral return of numerous 50 Cent clips to the forefront of pop culture, as his words seemed to come true like prophetic fortunes. As sexual assault allegations from men and women alike began flooding to the mogul’s name, 50’s comments about Diddy’s bizarre proclivities suddenly didn’t seem so far-fetched. Likewise, when Diddy associate Keefe D was arrested as part of an alleged conspiracy to murder Tupac Shakur back in 1996, Fif’s allegations about Diddy’s hand in the shooting seemed to ring true.

Diddy’s downfall really began in November of 2023, when his former girlfriend and Bad Boy signee Cassie Ventura sued him for sexual assault, battery and a host of other heinous crimes. From there, a snowball effect began spinning out of control, with headline-grabbing stories published near-daily until Diddy’s eventual arrest in September 2024. Needless to say, 50 Cent was present online for every one of these stories, sharing a wide array of viral comedic takedowns and humorously shopped photographs. The “21 Questions” vocalist helped to popularize phrases such as “no Diddy,” and even announced his intention to develop a documentary about the mogul humorously titled Diddy Do It.

When Will 50 Cent’s Diddy Documentary Air?

Like many of 50 Cent’s jokes, the documentary turned out to be more than just a social media caption. In the midst of Diddy’s downfall, it was reported that Netflix had acquired the rights to Diddy Do It after an intense multi-million dollar bidding war. Other streamers have already rushed to produce their own Diddy coverage, though 50 Cent promises that his docu-series will be extremely comprehensive, spanning decades of abuse and misconduct. As we know, 50 has the receipts to prove it, since he’s been making note of Diddy’s bizarre behavior since their earliest encounters.

Per a report in Variety, 50 Cent explained, “This is a story with significant human impact. It is a complex narrative spanning decades, not just the headlines or clips seen so far. We remain steadfast in our commitment to give a voice to the voiceless and to present authentic and nuanced perspectives. While the allegations are disturbing, we urge all to remember that Sean Combs’ story is not the full story of hip-hop and its culture. We aim to ensure that individual actions do not overshadow the culture’s broader contributions.” Alexandria Stapleton has signed on to direct, though there is currently no concrete information on the series’ release date.

The Future of 50 Cent and Diddy

Obviously, 50 Cent is far from finished with his decades-long feud. Diddy is currently incarcerated in a Brooklyn prison, having repeatedly been denied bail. His trial is set to begin in May 2025, leaving plenty of time for 50 and company to complete the first leg of their documentary. As the trial continues to unfold, plenty of new information is certain to come to light. In the meantime, fans are tuned in to 50 Cent’s social media pages, awaiting frequent updates on the rapper’s new film studio developments and much more.