A new video has emerged showing Rosie O’Donnell joking about how Sean “Diddy” Combs may have had legal trouble long before his recent arrest.
O’Donnell, who hosted the 2000 Grammy Awards, discussed the preparation for the event on her former talk show, “The Rosie O’Donnell Show,” ahead of the big night.
In one segment, O’Donnell is chatting backstage with the R&B group TLC, which was nominated for several awards that year.
“Do you want to hear a joke of mine?” she asked the three. “Ready? This is a good one. Let’s see if you like it.”
“A lot of people are nominated for multiple awards — multiple Grammy nominations — this year. Lauryn Hill got four, TLC got eight, and Sean Combs got five to 10.”
TLC members Lopes and Thomas looked stunned, their mouths hanging open before bursting into laughter.
“See? Like, is he going to jail?” O’Donnell explained, making Thomas laugh uncontrollably and hug her.
O’Donnell then told another joke about Diddy:
“I don’t mean that in a bad way, because he’s a nice guy and can actually sing. Oh!” she exclaimed, happily covering her mouth as the TLC members burst into laughter.
back in 2000 when Rosie O’Donnell criticized Diddy and predicted he would go to jail while TLC laughed! 🤣 photo.twitter.com/r7RrsheWij
— 𝙏𝙇𝘾𝙁𝙐𝙇𝙁𝙄𝙇𝙇𝙀𝘿 (@TheTLCVault) September 23, 2024
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The term “sing sing” refers to Sing Sing Prison, a maximum security prison located in Ossining, New York.
At the time, O’Donnell’s jokes may have been a reference to Diddy’s legal troubles, which were reported in the media.
Among them was a 1996 misdemeanor charge of criminal damage to property, according to court records, in which he allegedly threatened a photographer with a gun.
Additionally, in 1999, there was an incident where a woman claimed that the Bad Boy Records mogul shot her at a New York City nightclub, as reported by multiple news outlets at the time.
Last week, Diddy was arrested on charges related to sex trafficking and extortion.
According to court records, he has been denied bail twice despite efforts by his legal team.
The rapper is currently being held in a special housing unit at the Metropolitan Detention Center. Prosecutors successfully argued that Diddy was a flight risk, leading to the decision.
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Tags P. diddy, Diddy, Sean Combs, Rosie O’Donnell