Jokes about Sean “Diddy” Combs’ wild lifestyle have been floating around Hollywood for years, but one resurfaced clip from 2000 now feels eerily prophetic given his recent legal issues.
Rosie O’Donnell’s quip about Diddy’s potential prison time, made more than two decades ago, has fans raising their eyebrows in light of his September arrest.
A resurfaced video from “The Rosie O’Donnell Show,” which has gone viral thanks to a repost from “Entertainment Tonight,” features O’Donnell alongside Lisa “Left Eye” Lopes, Rozanda “Chilli” Thomas, and Tionne “T-Boz” Watkins of TLC during a pre-Grammy interview.
As the group chatted, O’Donnell couldn’t resist poking fun at Combs, who was entangled in legal troubles at the time.
She joked, “A lot of multiple nominees, multiple Grammy nominees this year. Lauryn Hill’s got 4, TLC’s got 8, and Sean Combs 5 to 10.”
O’Donnell then added, “He can really sing sing,” a clever reference to the notorious maximum-security prison in Ossining, New York.
The TLC trio burst out laughing at O’Donnell’s sharp humor, showing that even back then Combs’ legal woes were the talk of the entertainment world.
At the time, Diddy was embroiled in the fallout from a 1999 nightclub shooting at Club New York involving his artist Shyne Barrow. The incident left Combs facing legal heat, while Shyne ended up serving time in prison.
Fast-forward to 2024, and O’Donnell’s joke seems less like a punchline and more like a striking premonition. The jokes under the video on YouTube were just as spot-on.
“Diddy: Every breath you take, every move you make. FBI: I’ll be watching you,” one person said.
Another person said, “Wendy Williams called it every week.”
Social media users quickly latched onto the clip, commenting on it and giving their insight. When posted by YouTuber Jamel_AKA_Jamal, his followers poured into the comment section.
back in 2000 when Rosie O’Donnell shaded Diddy and predicted him going to jail while TLC busted out laughing! 🤣 pic.twitter.com/r7RrsheWij
— 𝙏𝙇𝘾𝙁𝙐𝙇𝙁𝙄𝙇𝙇𝙀𝘿 (@TheTLCVault) September 23, 2024
“When Diddy said he was innocent, Jennifer didn’t know where to put her face,” one comment read, referencing the old case. The user then went on to say, “This is not a prediction by Rosie, she knew what was up.”
One commenter said, “This is why Rosie’s show was cancelled. She wouldn’t keep the secrets. She was a real one.”
Another remarked, “It’s funny that Rosie O’Donnell has so much to say about P Diddy when she was at his parties participating in what was going on.”
In reality, O’Donnell clarified that despite being Diddy’s neighbor in Miami, she never attended one of his famous parties, though she was invited.
According to a TikTok video posted a day after his arrest, the “Sleepless in Seattle” actor said that she only met the party boy once. At the time, he invited her to a New Year’s Eve party at his home. However, when she and her family arrived, whoever was manning the door, turned them away at the door.
O’Donell said that Diddy called her the next day and told her that he “felt bad” about her not getting in, and to make up for the mishap he rented out an entire movie theater for her family the next day.
The extravagant gesture, O’Donnell called “unbelievably over-the-top.”
Interestingly, this resurfaced clip joins other celebrity accounts of Diddy’s legendary parties, including a story from comedian Kevin Hart.
In a widely shared video, Hart hilariously is seen with rapper Fabolous and singer Trey Songz at a “Dirty Money” listening party, where a woman’s hair caught fire while she was in a hot tub at one, further fueling the public’s fascination with “Been Around the World” chart-topper’s high-octane social life.
Despite her few experiences with Combs, O’Donell says he left her “in shock” over his recent legal troubles.
Diddy now faces a string of serious charges, including racketeering, sex trafficking, and transporting individuals for prostitution. The Emmy winner openly questioned how someone with such a public persona could engage in such alleged behavior.
“How could a person live knowing that they had done that and then be a public person and continue to do it?” she asked, adding, “Didn’t he feel the footsteps of the law behind him at all times?”
Many of her TikTok followers chimed in, celebrating her being one of the few high profile people to speak out about her experiences since his arrest.
“This is the first celebrity that I’ve seen speaking about Diddy. The silence in Hollywood is deafening,” one person wrote.
Another said, “You never know who is living next to you.”
A third person admitted, “This is very triggering for me,” to which O’Donnell replied, “Me too.”
“So scary how much he got away with for so long,” someone else stated.
As Diddy prepares to face these charges, the irony of O’Donnell’s long-forgotten joke is impossible to ignore as it gives a nod to years of bad boy behavior.
What once seemed like a lighthearted jab has taken on a much darker meaning in light of the allegations surrounding the music mogul.
