Rosie O'Donnell eerily 'predicts' Diddy's arrest in resurfaced behind-the-scenes Grammys footage with TLC

Rosie O'Donnell eerily predicted Sean 'Diddy' Combs' legal woes more than two decades ago before he was arrested on sex trafficking charges. 

In a resurfaced video taken ahead of the 43rd Annual Grammy Awards in 2000, the comedian, 62, made several jokes about foreseeing the rapper, 54, going to jail while talking 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 with the TLC members backstage about their multiple nominations that year.

'Wanna hear a joke I have?' she asked the girl group. 'Ready? This is good. See if you like it.' 

The mother-of-five went on to say: 'Lot of multiple nominees — multiple Grammy nominees — this year. Lauryn Hill's got four, TLC's got eight and Sean Combs 5 to 10.' 

The quip caused Lopes and Thomas to instantly start laughing, before quickly covering their mouths to hide their shocked expressions. 

To ensure the women understood her joke, O'Donnell clarified: 'Get it? Like, he's going to jail?' 

As she cracked up, Thomas gave O'Donnell a big hug. 

O'Donnell proceeded to poke even more fun of Diddy with another wisecrack at his expense. 

'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 alluding 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 its violence and poor inmate care,' according to BBC. 

O'Donnell jokes were most likely a nod to his legal problems, at the time, which included being found guilty of misdemeanor criminal mischief in 1996 for threatening a photographer with a gun. 

Additionally, he was accused of shooting a woman in a Manhattan night club in 1999. Ultimately, he was acquitted of all charges in connection with the shooting.

Following Diddy's arrest, O'Donnell expressed shock in a TikTok video as she recalled being his neighbor in Miami and her only interaction with him. 

'Although I only met him once, he did invite me to his New Year's Eve party. I believe everyone was wearing white, but we didn't know,' she told her fans.

O'Donnell, then, revealed that since she and her family were unaware of the dress code they were turned away at the door for wearing sweatpants. 

The next day, she said Diddy called her and said he felt 'so bad' about what happened and wanted to make it right.

To make amends, he rented out a Regal Cinema for her and her kids 'to see any movie' they wanted for 'the entire day in any theater whenever' they wanted. 

O'Donnell said the gift felt 'so unbelievably 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 indictment. 'And I know there is perhaps a naïveté to me in some way, but how could a person live knowing that they had done that and then be a public person and continue to do it?' 

She continued, 'Didn't he feel the footsteps of the law behind him at all time? Or do you just get to be so big, like Harvey Weinstein did, that he thought, "Well I control Hollywood. I control the Oscars. I can sleep with any actress I want whether they want to or not."' 

Diddy, who was denied bail, has pleaded not guilty to all three charges of racketeering, sex trafficking and transportation to engage in prostitution. 

The judge who will preside over his case agreed with prosecutors that he was a serious flight risk and that he posed a danger to others.