50 Cent’s Ex Chelsea Handler Didn’t Hold Back While Sharing Thoughts On Him Trolling Diddy

As Sean “Diddy” Combs remains in prison and continues to face numerous lawsuits, one fellow rapper has been particularly vocal – Curtis “50 Cent” Jackson. 56-year-old Combs and 50-year-old Jackson have long feuded with each other and, with that, Jackson hasn’t held his tongue on his peer’s issues. Aside from trolling Diddy, Fiddy also produced a docuseries on the embattled rapper. Now, one of Jackson’s ex-girlfriends, comedian Chelsea Handler, is weighing in on the trolling, and she made her opinion very clear.

How Does Chelsea Handler Feel About Her Ex Shading Diddy?

Years ago, Handler and Jackson were indeed in a relationship, which allegedly began and ended sometime in 2011. Handler (50) touched on her relationship with the G-Unit alum during a recent appearance on the We Might Be Drunk Podcast (as shared on YouTube). One of the hosts opined that Jackson had been having “a hell of a moment” due to making headlines for chastising Combs. Handler agreed, and she then expressed her delight over her former partner’s recent comments:

In addition to 50 Cent’s comments about Diddy, there’s something else that seems to give Chelsea Handler comfort. The comic, who recently hosted the Critics’ Choice Awards for the second consecutive year, also shared her appreciation for how Jackson “doesn’t ever talk shit about” her. That’s apparently significant, because the “In da Club” rapper allegedly doesn’t speak highly over his other exes during interviews. While Handler has seemingly avoided public critiques from Jackson, that definitely hasn’t been the case for Combs.

How Has 50 Cent Been Trolling Diddy?

Combs was arrested in September 2024 and eventually charged with sex-trafficking and racketeering. Throughout that time, 50 Cent took various jabs at Combs on social media, from calling out his legal team for doing him “dirty” and vowing to stop President Trump from pardoning him. Once Combs received a mixed verdict, Fiddy trolled him with yet another post. Jackson made headlines in a bigger way, though, when he announced his plans to make a documentary about his longtime rival.

50 Cent produced the four-part docuseries Sean Combs: The Reckoning, which became available to Netflix subscription holders in December 2025. Directed by Alexandria Stapleton, the doc explores Combs’ rise to power within the music industry as well as the legal issues and allegations that have plagued him in recent years. Combs took issue with the doc and accused Jackson and co. of using “stolen” footage for the production. Jackson and Stapleton have since denied the claims.

Amid the rollout for his docuseries, 50 Cent accepted the fact that some called him “petty” for making it. Fiddy also, however, clarified that his years-long feud with Diddy didn’t affect his decision to produce the doc, as he wanted to convey that not everyone in the hip hop industry contains Diddy’s actions. And, based on Chelsea Handler’s comments, it seems she’s quite pleased with her ex’s decision not to keep quiet on the matter.