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

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Entertainer Rosie O'Donnell hosts the show at the
LOS ANGELES, UNITED STATES: Entertainer Rosie O'Donnell hosts the show at the 42d Annual Grammy Award in Los Angeles 23 February, 2000. (ELECTRONIC IMAGE) AFP PHOTO / Hector MATA/hmb (Photo credit should read HECTOR MATA/AFP via Getty Images)
Social media is having a laugh at one of Rosie O’Donnell's old jokes about Diddy.

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.

Read More: Diddy Accuser's Attorney Claims They've Received Offers For Alleged Sex Tape

Diddy Arrested In New York City In 1999

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."

Rosie O’Donnell Jokes About Diddy Ending Up In Jail

Diddy's currently behind bars at the Metropolitan Detention Center in Brooklyn while awaiting trial. He's already pleaded not guilty. Check out the clip of O'Donnell trolling Diddy below. Be on the lookout for further updates on Rosie O’Donnell and Diddy on HotNewHipHop.

Read More: Diddy's (Alleged) Dirty Deeds: Sinister Stories & Scandals Throughout The Years

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About The Author
Cole Blake
Cole Blake is currently an Editor at HotNewHipHop based out of Brooklyn, New York. He began working at the site as an intern back in 2018 while studying journalism at St. John’s University. In the time since, he’s graduated with a bachelor's degree and written extensively about a wide range of topics including pop culture, film & television, politics, video games, sports, and much more. He’s also covered music festivals such as Gov. Ball and Rolling Loud. You can find him publishing work for HNHH from Monday to Wednesday or on weekends. On the sports front, Cole’s a passionate NBA and NFL fan with his favorite teams being the Indianapolis Colts and Los Angeles Lakers. He also roots for the Yankees whenever he finds himself at Yankee Stadium or the Red Storm when in the company of other SJU alumni. His favorite hip-hop artists are billy woods, Earl Sweatshirt, Cam’ron, MIKE, and Mach-Hommy.
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