Jokes about Sean “Diddy” Combs’ wild lifestyle have been circulating in Hollywood for years, but one clip from 2000 that has resurfaced now seems eerily prescient given his recent legal troubles.

Rosie O’Donnell’s joke about Diddy’s potential prison sentence, made greater than twenty years ago, raised eyebrows amongst fans following his September arrest.

A video from ‘The Rosie O’Donnell Show’ has resurfaced and gone viral because of: repost “Entertainment Tonight” features O’Donnell alongside TLC’s Lisa “Left Eye” Lopes, Rozanda “Chilli” Thomas and Tionne “T-Boz” Watkins during a pre-Grammy interview.

During the group conversation, O’Donnell couldn’t help but make fun of Combs, who was in legal trouble on the time.

She joked, “There are a whole lot of nominees this 12 months, a whole lot of Grammy nominees. Lauryn Hill has 4, TLC has 8 and Sean Combs has 5 to 10.

O’Donnell then added, “He can really sing” – a clever reference to the notorious maximum security prison in Ossining, New York.

The TLC trio burst into laughter at O’Donnell’s sharp humor, showing that Combs’ legal problems were already the talk of the entertainment world.

At the time, Diddy was embroiled within the aftermath of the 1999 Club New York nightclub shooting involving fellow artist Shyne Barrow. As a results of the incident, Combs was placed on trial and Shyne was sent to prison.

Fast forward to 2024, and O’Donnell’s joke seems less like a punchline and more like a striking prediction. Jokes below video on YouTube were equally accurate.

“Diddy: Every breath you are taking, every move you make. FBI: I’ll be watching you,’ one person said.

Another person said: “Wendy Williams called this every week.”

Social media users quickly picked up on the clip, commenting on it and sharing their thoughts. When sent by YouTuber Jamel_AKA_Jamal, his followers began flocking to the comments section.

in 2000 when Rosie O’Donnell threw shade at Diddy and predicted he would go to jail while TLC erupted in laughter! 🤣 pic.twitter.com/r7RrsheWij

— 𝙏𝙇𝘾𝙁𝙐𝙇𝙁𝙄𝙇𝙇𝙀𝘿 (@TheTLCVault) September 23, 2024

“When Diddy said he was innocent, Jennifer didn’t know where to put her face,” reads one in every of the comments, referring to the old case. The user then added: “It’s not Rosie’s prediction, she knew what was happening.”

One commenter said: “This is why Rosie’s show was cancelled. She didn’t want to keep secrets. She was real.”

Another noted, “It’s funny that Rosie O’Donnell has so much to say about P. Diddy when she was at his events and was involved in what was going on.”

In fact, O’Donnell explained that despite the fact that she is Diddy’s neighbor in Miami, she has never been to one in every of his famous parties, although she was invited.

According to a TikTok video sent a day after his arrest, the “Sleepless in Seattle” actress said she only met the party animal once. He then invited her to a New Year’s Eve party at his house. But when she and her family arrived, the door attendant turned them away.

O’Donell said Diddy called her the following day and said he “felt bad” about her absence, so to treatment his unhappiness, he rented out your entire movie show to her family the following day.

An extravagant gesture, O’Donnell called “incredibly excessive.”

Interestingly, this re-posted clip joins other celebrity accounts of Diddy’s legendary parties, including comedian Kevin Hart’s story.

In a widely shared video, Hart is hilariously seen with rapper Fabolous and singer Trey Songz at a ‘Dirty Money’ listening party, where a girl’s hair caught fire while she was in a hot tub, further fueling the gang’s fascination with ‘Been’ Around the World’ – stuffed with social life, top places on the charts.

Despite her limited experience with Combs, O’Donell claims he left her “shocked” by his recent legal problems.

Diddy now faces various serious charges, including racketeering, sex trafficking and transporting people for prostitution. The Emmy winner openly questioned how someone with such a public personality could engage in such alleged behavior.

“How can someone live knowing they did it and then be a public figure and still do it?” – she asked, adding: “Didn’t he feel the footsteps of the law behind him the whole time?”

Many of her TikTok followers joined in, celebrating that she is one in every of the few high-profile people to share her experiences since his arrest.

“This is the primary celebrity I’ve seen talking about Diddy. The silence in Hollywood is deafening,” one person wrote.

Another said: “You never know who lives next to you.”

A 3rd person admitted: “This is very touching to me,” to which O’Donnell replied: “Me too.”

“It’s scary how much he’s managed to get away with for so long,” said one other.

As Diddy prepares to face these accusations, the irony of O’Donnell’s long-forgotten joke, which is a nod to the boy’s years of misbehavior, can’t be ignored.

What once appeared like a lighthearted jab has taken on a much darker meaning in light of the allegations surrounding the music mogul.