A video has resurfaced featuring Rosie O'Donnell making a joke about Sean "Diddy" Combs possibly encountering legal issues long before his recent arrest.
O'Donnell, who hosted the Grammy Awards in 2000, discussed the event preparations on her former talk show, "The Rosie O'Donnell Show," before the big night.
In one segment, O'Donnell was backstage chatting with the R&B group TLC, who were nominated for several awards that year.
"Wanna hear a joke I have?" she asked the trio. "Ready? This is good. See if you like it."
"Lot of multiple nominees — multiple Grammy nominees — this year. Lauryn Hill's got four, TLC's got eight and Sean Combs 5 to 10."
TLC members Lopes and Thomas appeared shocked, their jaws dropping before erupting into fits of laughter.
"Get it? Like, he's going to jail?" explained O'Donnell, prompting Thomas to laugh uncontrollably and hug her.
O'Donnell then made another joke about Diddy:
"I don't mean to be mean because, I mean, he's a nice guy and he can really sing sing. Oops!" she exclaimed, playfully covering her mouth while the TLC members burst into laughter.
back in 2000 when Rosie OβDonnell shaded Diddy and predicted him going to jail while TLC busted out laughing! π€£ pic.twitter.com/r7RrsheWij
— πππΎπππππππππΏ (@TheTLCVault) September 23, 2024
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The "sing sing" reference was to Sing Sing Correctional Facility, a maximum-security prison located in Ossining, New York.
At the time, O'Donnell's jokes likely alluded to Diddy's legal troubles that had been reported in the media.
These included a misdemeanor charge in 1996 for criminal mischief, where he allegedly threatened a photographer with a gun, according to court records.
Additionally, in 1999 there was an incident where a woman claimed the Bad Boy Records mogul shot her at a nightclub in New York City, as reported by multiple news outlets at the time.
Last week saw the arrest of Diddy on charges related to sex trafficking and racketeering.
He has been denied bail twice despite the efforts of his legal team, as reported by court documents.
The rapper is currently being held in a specialized housing unit at the Metropolitan Detention Center. Prosecutors successfully argued that Diddy posed a flight risk, leading to the decision.
READ MORE: Diddy's 'Adopted Daughter' Drama Takes Strange Turn Amid Arrest Fallout
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