Fashion’s biggest night, a.k.a. the 2025 Met Gala, is set to take place on Monday May 5) But, there’s one notable face who definitely won’t be there to partake in the festivities: Sean “Diddy” Combs.
In fact, the disgraced hip-hop mogul is behind bars and will instead be gearing up for his federal sex trafficking trial, of which jury selection is also taking place on Monday. However, contrary to what some people may believe, Combs has been somewhat of a regular at the Met Gala, making his first appearance back in 2003. He would later attend a total of six more times since then with the latest one being his show-stopping appearance in 2023 where he showed up with rapper Yung Miami of the City Girls.
But, given the tumultuous year and a half he’s had given the shocking allegations of racketeering conspiracy and engaging in interstate transportation for prostitution, Combs will be trading in his designer suits for a more demure and limited look as his legal fate plays out over the next few weeks.
So, we thought it’d be fitting to take a look back at some of his most iconic Met Gala moments over the years because let’s face it—ain’t no telling if or when he’ll ever be able to stunt on these steps again.
Diddy Gives Cassie the “Death Stare”- 2015
OK, so when we said iconic—we didn’t necessarily mean iconic in a positive way and this moment between Diddy, his then-girlfriend Cassie Ventura, Vogue’s former Editor-At-Large, the late Andre Leon Talley just proves it. For context, it was Ventura’s bombshell sexual assault lawsuit in that served as the first domino to fall in Diddy’s world back in 2023.
But there may have been signs years before that there was trouble brewing beneath the surface as evidenced by this troubling interaction at the 2018 Met Gala. As seen in the clip above, when Ventura and Diddy walked up to speak to Talley, the Bad Boy founder gives his girl a menacing glare as she’s complimented on her dress. Given what we know now about how much control Diddy allegedly had over her and his mistreatment of her, hindsight of this moment is visibly disturbing.
Diddy Silently Dares Cassie to Speak- 2018
In yet another menacing moment, back at the 2018 Met Gala, Diddy and Ventura were once again stopped on the carpet for interviews. With the theme being “Heavenly Bodies: Fashion & The Catholic Imagination,” interviewer Liza Koshy jokingly asked Ventura if there was anything she wanted to confess while speaking. That question quickly prompted Diddy to shoot yet another scary stare at her as she sidestepped the question and kept it calm and cute.
“I keep everything right here or right here,” she said motioning to her heart and then to Diddy.
Thankfully, her response was enough to get a smile out of the “I’ll Be Missing You” star.
Diddy Doesn’t Look To Amused- 2023
In red carpet footage from the 2023 gala, Diddy can be seen taking photos momentarily by himself. While we previously told you he was there in attendance with his then-girlfriend Yung Miami, when posing for pics alone, the hip-hop leader doesn’t appear all too thrilled to be there.
Perhaps it was because he knew just six months later, Ventura would hit him with that shocking sexual abuse lawsuit. We do know that both the “Me and U” singer’s and Diddy’s legal teams met prior to her filing the suit and she was reportedly offered “eight figures” for her silence. Clearly, Ventura denied the offer and we all know what transpired after that.
“After all the news about him, he looks scared to death,” wrote one user in the comments section of the post.
Given the possible lifetime in prison sentence he’s facing and the litany of allegations and lawsuits that came about in the months after this appearance, I’d be scared too.