A resurfaced clip featuring Rosie O’Donnell humorously speculating that Sean “Diddy” Combs might one day serve “5 to 10 years” in prison has gained attention due to the music mogul’s escalating legal problems.
During a pre-Grammy video appearance back in 2000 with TLC members Tionne “T-Boz” Watkins, Lisa “Left Eye” Lopes, and Rozonda “Chilli” Thomas, O’Donnell lightheartedly addressed the numerous Grammy nominees that year. “Wanna hear a joke I have? Ready? This is good. See if you like it,” she quipped.
O’Donnell then launched into her joke, noting the impressive nominations across the board: “Lauryn Hill’s got four, TLC’s got eight, and Sean Combs 5 to 10.” The gag elicited laughter from Lopes and Thomas before their faces shifted to expressions of disbelief.
“Get it? Like, he’s going to jail?” O’Donnell clarified, more than two decades before the recent accusations against Combs related to sex trafficking.
In her comedic style, she added, “I don’t mean to be mean because, I mean, he’s a nice guy and he can really sing sing. Oops!” alluding to the idea of a New York prison.
Recently, O’Donnell addressed Combs’ arrest on TikTok, drawing parallels to Harvey Weinstein, who was arrested in 2018 on rape and sexual assault charges. She expressed disbelief at how someone like Combs, with significant influence, might not perceive the repercussions of his actions.
“Didn’t he feel the footsteps of the law behind him at all times? Or do you just get to be so big like Harvey Weinstein that he thought, ‘Well, I control Hollywood. I can sleep with any actress I want whether they want to or not,’” she posed, questioning how Combs could avoid recognizing his alleged misconduct.
The allegations facing Combs are serious. He was arrested on September 16 in Manhattan, facing charges related to racketeering conspiracy, sex trafficking, and transportation for prostitution. Prosecutors allege that the 54-year-old music producer has been involved in a pattern of abusing, threatening, and coercing women and others for years to satisfy his sexual desires while maintaining his public image.
The indictment suggests Combs may have created an extensive criminal enterprise involving sex trafficking, forced labor, and other serious offenses. O’Donnell expressed her concern about the disturbing nature of these allegations, contemplating how many individuals may have been aware of Combs’ actions over the years.
