Rosie O’Donnell Jokes About Diddy Ending Up In Jail In Resurfaced Clip

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A video of Rosie O’Donnell trolling Diddy for his 1999 arrest in New York City from the 2000 Grammys is recirculating on social media in the wake of the 14-page federal indictment he now faces. In the clip, the comedian jokes about him ending up behind bars while speaking with TLC’s Tionne “T-Boz” Watkins, Lisa “Left Eye” Lopes, and Rozonda “Chilli” Thomas.

“Wanna hear a joke I have? Ready? This is good. See if you like it,” O’Donnell began. “Lot of multiple nominees, multiple Grammy nominees, this year. Lauryn Hill’s got four, TLC’s got eight, and Sean Combs – five to 10. Get it? Like, he’s going to jail?” The members of TLC then burst into laughter, which prompted O’Donnell to add: “I don’t mean to be mean, because, I mean, he’s a nice guy and he can really sing sing. Oops!” Diddy was eventually found not guilty on all charges from 1999, however, authorities arrested him again for separate charges of sex trafficking and racketeering, earlier this month.

Music producer P. Diddy, Puffy, Diddy, Puff Daddy, Puff (real name: Sean Combs) was arrested by the NYPD in December. 1999 and charged with possession of a firearm following a shooting at a Manhattan nightclub. (Photo courtesy Bureau of Prisons/Getty Images)

Speaking with TMZ, his attorney confirmed that he won’t be pursuing a plea deal and instead plans to argue his case in court. “It’s not up to me. It’s up to Mr. Combs, and I don’t see it happening because he believes he’s innocent,” Attorney Marc Agnifilo told the outlet. “He believes that he needs to stand up not just for himself (but) his family and for everybody who’s been targeted by the federal government. He feels an obligation to those people to say, ‘You know what? Maybe I can break the model. Maybe I can show the world that a Black man can win in federal court.’ And I think he might be the only person I know of to be able to accomplish that.”