Diddy Mocked With Jail Joke By Rosie O’Donnell in Viral Grammys Clip

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Rosie O’Donnell is once again in the spotlight after an old video of her making fun of Sean “Diddy” Combs resurfaced online.


The footage, dating back to the 2000 Grammys, shows O’Donnell joking about Combs potentially facing jail time.

Posted on Twitter/X on September 24, the clip quickly gained traction, amassing over 700,000 views.

In the video, O’Donnell, now 62, was seen sharing laughs with TLC members 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 begins in her pre-show chat with the group. “Lot of multiple nominees, multiple Grammy nominees, this year. Lauryn Hill’s got four, TLC’s got eight and Sean Combs – five to 10.”

The implication of a “five to 10” year prison sentence immediately hit home with the TLC members, who burst into laughter while covering their faces.

O’Donnell continued, “Get it? Like, he’s going to jail?”

She wrapped up the joke with another quip about New York’s maximum-security facility, Sing Sing.

“I don’t mean to be mean,” she said, “because, I mean, he’s a nice guy and he can really sing sing. Oops!”

Currently, the 54-year-old Combs is serving time at the Metropolitan Detention Center in Brooklyn on charges that include sex trafficking, racketeering, and transportation to engage in prostitution.

He has pleaded not guilty to the charges.