Rosie O’Donnell eerily predicted Sean “Diddy” Combs’ legal troubles more than two decades ago, before he was arrested for sex trafficking.
In a resurfaced video taken ahead of the 43rd Annual Grammy Awards in 2000, the 62-year-old comedian made several jokes about predicting the rapper, 54, would go to jail while speaking to Tionne “T-Boz” Watkins, Lisa “Left Eye” Lopes and Rozonda “Chilli” Thomas.
While filming a behind-the-scenes special for her now-defunct talk show, The Rosie O’Donnell Show, the star spoke backstage with TLC cast members about their many nominations that year.
“You want to hear a joke I have?” she asked the girl group. “Ready? This is good. See if you like it.”
The mother of five added, “A lot of multiple nominees — multiple Grammy nominees — this year. Lauryn Hill has four, TLC has eight, Sean Combs has 5 to 10.”
Rosie O’Donnell eerily predicted Sean ‘Diddy’ Combs’ legal troubles more than two decades ago, before he was arrested on sex trafficking charges
Lopes and Thomas immediately started laughing at this joke, but they quickly covered their mouths to hide their shocked expressions.
To make sure the women got her joke, O’Donnell clarified, “You get it? He’s going to jail?”
As she burst out laughing, Thomas gave O’Donnell a big hug.
O’Donnell made more jokes about Diddy, with another joke about him.
“I don’t mean to be mean, because I mean, he’s a nice guy and he can really sing, sing. Oops!” she mused.
The actress was referring to Sing Sing Correctional Facility, a maximum-security prison in Ossining, New York.
Diddy, who was arrested last week, is currently being held at the Metropolitan Detention Center in Brooklyn, which is reportedly “notorious for violence and poor care of its inmates.” BBC.
O’Donnell’s jokes were likely a nod to his legal troubles at the time, when he was found guilty of a misdemeanor in 1996 for threatening a photographer with a gun.
Diddy, who was arrested last week, has pleaded not guilty to all three charges of racketeering, sex trafficking and transportation to engage in prostitution (seen in May 2024)
Additionally, he was accused of shooting a woman to death at a Manhattan nightclub in 1999. He was eventually acquitted of all charges related to the shooting.
Following Diddy’s arrest, O’Donnell expressed his shock in a TikTok video in which she recalls being his neighbor in Miami and that was the only time she had contact with him.
“Even though I only met him once, he invited me to his New Year’s party. I think everyone was wearing white, but we didn’t know that,” she told her fans.
O’Donnell then said that she and her family were not aware of the dress code and were turned away at the door for wearing sweatpants.
She said Diddy called her the next day and said he felt “so bad” about what had happened and wanted to make it right.
To make it up to her, he rented a Regal Cinema for her and her children so they could watch any movie they wanted “all day long in any theater, whenever they wanted.”
In a resurfaced video taken ahead of the 43rd Annual Grammy Awards in 2000, the 62-year-old comedian made several jokes about predicting the rapper, 54, would go to jail while speaking with Tionne “T-Boz” Watkins, Lisa “Left Eye” Lopes and Rozonda “Chilli” Thomas
While filming a special behind-the-scenes taping for her now-defunct talk show, The Rosie O’Donnell Show, O’Donnell spoke to TLC members backstage about their many nominations that year.
O’Donnell said the gift felt “so incredibly over the top and extraordinary.”
She noted that they never spoke again after that day.
“I’m just kind of in shock,” O’Donnell said of his charges. “And I know I may be naive in some ways, but how can someone live with the knowledge that they did something like this and then be a public figure and continue to do it?”
She continued: ‘Didn’t he feel the law behind him all the time? Or do you just get so big, like Harvey Weinstein, that he thought, “Well, I control Hollywood. I control the Oscars. I can sleep with any actress I want, whether they want me to or not.”‘
Following Diddy’s arrest, O’Donnell expressed her shock in a TikTok video, in which she recalled being his neighbor in Miami and her only interaction with him was
Diddy, who was denied bail, pleaded not guilty to all three charges: extortion, sex trafficking and transportation for the purpose of prostitution.
The judge hearing his case agreed with prosecutors that he posed a serious flight risk and a danger to others.