50's been trolling long before the term became in vogue.

1/8/2026

50 Cent attends Dick Clark's New Year's Rockin' Eve on Dec. 31 2025. Gilbert Flores

50 Cent is a generational hater. Let’s take it a step further: he’s on the Mount Rushmore of haters. The G-Unit mogul is as petty as they come in beef and there’s no line he won’t cross to make his opps question why they would ever want to feud with him in the first place.

50’s been trolling way before it became a popular term among millennials and part of the DNA of the social media zeitgeist.

In part, his rap career took off because of trolling with his breakout “How to Rob” single in 1999, which found him hypothetically mugging Diddy, Keith Sweat, Mase and Master P. He remains entrenched in a cold war with a few of the “How to Rob” targets decades later, like Jay-Z and Diddy, the latter of whom 50 claims his beef started with after Combs asked to take him shopping.

While 50 isn’t dominating the charts and cooking up club anthems in a bulletproof vest like it’s the mid-2000s, as his focus has switched to his G-Unit Film/TV production company and spirits empire, the Queens icon’s unfiltered opinions still move the needle globally.

Trolling has long been part of the equation in rap beefs, and 50 has the cleverness, audacity and catalog to back it up in battle. 50’s antagonizing antics that landed on his ThisIs50 website were ahead of their time. He’s got a PHD diploma in understanding the internet, and has shown a shrewd ability to evolve in the digital era. At the same time, many of the 50-year-old’s peers would probably pronounce meme incorrectly.

While he seems to take joy in emasculating his opponents, 50 says he doesn’t take his art of war too seriously. “None of that is really personal, it’s just me having fun at the end of the day,” 50 told Hot 97 in 2024.

With victims ranging from Fat Joe to DJ Khaled and Rick Ross, here we recall some of 50 Cent’s most memorable trolling moments over the years.

• Juelz Santana’s Missing Teeth

  Date: November 2018

  50 clowned Juelz Santana for what appeared to be the Dipset rapper missing teeth in the “Sauce Boyz” video. “Damn it Mmaaannn just say no to drugs. This is going to far now, ‍no teeth Jesus Christ Positive vibes,” the G-Unit boss wrote to IG. Santana then popped out with a fresh set of veneers.

• Jay-Z’s Close-Up

  Date: May 2024

  While the sexual assault lawsuits continued to pile up for Diddy, 50 attempted to rope Jay-Z into the mess by posting a close-up picture of Hov with his features enlarged. “Jay in hibernation he ain’t coming outside till this shit with puff blow over, no brunch, no lunch, No dinner. LOL IM ALL YOU GOT IM OUTSIDE,” he captioned the post on Instagram.

  This was also prior to the civil sexual assault lawsuit filed against Diddy and Jay, which accused Jay-Z of raping a 13-year-old girl in 2000. The December 2024 suit was voluntarily dismissed by the accuser and Jay filed a defamation countersuit.

• They Took My Oil Also

  Date: January 2026

  Following the arrest of Venezuelan President Nicolás Maduro, 50 mocked Diddy by posting a political cartoon of Combs and Maduro as bunkmates inside a jail cell. “They took my oil too,” Diddy says in the cartoon, which finds him braiding Maduro’s hair. “Good morning ladies and gentlemen, may today be productive and prosperous towards you and your goals. Make your enemies watch your progress repeatedly,” 50 captioned the post, which has over 1 million likes on IG.

• No More Child Support

  Date: October 2022

  50 put his son, Marquise Jackson, on blast with a hilarious skit mocking him over the then-25-year-old complaining that $6,700 in child support monthly wasn’t enough to “rebuild” his life. 50 enjoys a cigar and a bubble bath while making fun of his estranged kid. Uncle Murda and Tony Yayo then show up at his front door, asking for $6,700 a month to help pay bills and get by.

• Free Diddy

  Date: May 2025

  50 pulled up courtside to a New York Knicks-Indiana Pacers game in the 2025 NBA Playoffs and posted a Photoshopped picture of himself rocking a t-shirt that was emblazoned with a “Free Diddy” logo as Combs remained locked up on federal sexual abuse charges awaiting trial.

Get weekly rundowns straight to your inbox

Sign Up