WATCH: Old Grammys clip showing Rosie O'Donnell predicting Diddy's arrest over 20 years ago goes viral

LOS ANGELES, CALIFORNIA: Rosie O'Donnell's old jokes about Sean "Diddy" Combs' potential prison time have resurfaced at a time when the music mogul is confronting significant legal challenges.

More than two decades after O'Donnell playfully predicted Diddy’s legal woes during a backstage chat at the 2000 Grammy Awards, fans and commentators alike are stunned after Diddy was arrested on multiple charges.

The video was posted on Twitter/X on September 24 and quickly went viral, accumulating over 700,000 views. The comedian also recently shared her thoughts on her brief encounter with Diddy, unveiling a surprising story that adds an intriguing dimension to the ongoing drama surrounding his arrest.

Rosie O'Donnell joked about Sean 'Diddy' Combs' fate two decades ago

In a resurfaced video from the 2000 Grammy Awards, Rosie O'Donnell, 62, joked about predicting that Sean "Diddy" Combs', 54, would end up in jail while conversing with TLC members Tionne "T-Boz" Watkins, Lisa "Left Eye" Lopes, and Rozonda "Chilli" Thomas.

During a behind-the-scenes segment for her now-defunct talk show, 'The Rosie O'Donnell Show', she chatted with the TLC members about their nominations that year. “Want to hear a joke I have?” she asked. “Ready? This is good. See if you like it.”

O'Donnell continued, “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 joke elicited laughter from Lopes and Thomas, who quickly covered their mouths in shock.

To emphasize her punchline, O'Donnell explained, “Get it? Like, he’s going to jail?” As she chuckled, Thomas embraced her warmly.

O'Donnell continued to tease Diddy, saying, “I don't mean to be mean because, I mean, he's a nice guy and he can really sing sing. Oops!” This playful jab referenced Sing Sing Correctional Facility, a maximum-security prison in New York.

Diddy was arrested last week and is currently being held at the Metropolitan Detention Center in Brooklyn, known for its violence and inadequate inmate care.

O'Donnell's jokes likely alluded to Diddy's past legal troubles, including a 1996 misdemeanor conviction for threatening a photographer with a gun.

Internet claims Rosie O'Donnell 'is right' about Sean 'Diddy' Combs

After discovering Rosie O'Donnell's resurfaced video where she predicted Sean "Diddy" Combs' potential prison time, numerous fans have flocked to the comment section to express their thoughts.

One user on X claimed, "Great women who knew what a monster Diddy is." The second user shared, "OMG damn. She had it out for him!"

One individual said, “Omg the Sing Sing joke lol it’s a shame she turned into such a troll.”

One user on Facebook claimed, "She's right about him." Another stated, "How sick it took so long … should have made straight up allegations instead of jokes."

A person hailed, “O’Donnell is one insightful guy!” Another social media user claimed, “But she was just over on tik tok [sic] acting like she didn’t know anything and all shocked. 🤔🧐 And how her family only went to one party and he bought the movie theater out for them for some reason.”

A user also added, “Rosie, was a mess back in the day! Use to love her show! She was too funny! Diddy, was a terror since way back then. Then it got worse and worse. 👀😆🤣"

Rosie O'Donnell reflects on Sean 'Diddy' Combs' arrest and their past encounter as neighbors

Following Sean "Diddy" Combs' recent arrest, Rosie O'Donnell shared her surprise in a TikTok video, reminiscing about their only interaction as neighbors in Miami.

"Although I only met him once, he invited me to his New Year's Eve party," she shared, recalling how everyone was dressed in white, which she and her family didn't know. "We were turned away for wearing sweatpants."

The following day, Diddy called to apologize and offered to make it up to her by renting out a Regal Cinema for her and her kids, giving them the opportunity to enjoy any movie they wanted for an entire day.

O'Donnell described the gesture as “so unbelievably over the top and extraordinary,” although she mentioned that they never spoke again after that, as per the Daily Mail.

Reflecting on his indictment, O'Donnell said, “I'm just kind of in shock. 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 added, "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.'"

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