Back in the late 90s to early 2000s, Rosie O’Donnell was given the nickname “Queen of Nice,” for her lighthearted and witty banter with guests and for her philanthropic works, and in 2000, O’Donnell was asked to host the 42nd Grammy Awards.
Known for her quick wit and sharp humor, Rosie has cracked jokes throughout her career—but who would have thought she could also predict the future? While rehearsing for the Grammy Awards, members of the popular girl group TLC—Rozonda “Chilli” Thomas, Tionne “T-Boz” Watkins, and Lisa “Left Eye” Lopes—joined her in going over jokes. The moment was captured while the singers were rehearsing for the awards show.
In the now resurfaced video, Rosie tests out jokes that she planned on using for the Awards show. She asked the girls:
“Wanna hear my joke, I have? Ready? This is good. See if you like it.”
Rosie continues after the girls prod her to tell the joke:
“Lot of multiple nominees. Multiple Grammy nominees this year. Lauryn Hill’s got four, TLC’s got eight, and Sean Combs 5 to 10.”
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
A pause from the girls, followed quickly by laughter from the four women after getting the joke.
Lisa when she got the joke is dead taking me out 😭😭😭😭😭 pic.twitter.com/5xrLiM13nW
— 𝙏𝙇𝘾𝙁𝙐𝙇𝙁𝙄𝙇𝙇𝙀𝘿 (@TheTLCVault) September 24, 2024
Rosie then explains:
“Get it? Like, he’s going to jail?”
To which “Chilli” laughs so hard, she ends up wrapping her arms around O’Donnell for support.
Rosie wasn’t done, and added another joke:
“I don’t mean to be mean because, I mean, he’s a nice guy and he can really sing sing. Oops!”
Referring to Sing Sing Correctional Facility in New York.
Okay, maybe Rosie isn’t a psychic-slash-fortune teller, but it was pretty spot-on. At the time, Sean “Diddy” Combs was at the forefront of news outlets for a 1999 shooting incident at Club New York in Manhattan where a woman named Natania Reuben claims Combs shot her in between her eyes. She was one of three who were allegedly shot during that incident. Reuben even came out recently maintaining her stance and spoke about the issue:
“Who better to tell you what happened than the person who got shot smack dab in between my eyes?”
Diddy seems to predict his arrest in resurfaced 1999 interview with ET:
“You’re gonna hear about my parties. They’re gonna be shutting them down […] probably be arresting me […] just cause we wanna have a good time.”
— Pop Base (@PopBase) September 23, 2024
In 2011, Combs settled with the three victims for an undisclosed amount. Just recently, Combs was arrested at the lobby of a New York City hotel and was charged with “racketeering conspiracy, sex trafficking and transportation to engage in prostitution.” Already controversial, the case went even more viral after police found 1000 bottles of baby oil in Combs’ home to which his lawyer Marc Agnifilo said,
“He has a big house, he buys in bulk. think they have Costcos in every place where he has a home.”
Federal Agents found 1,000+ bottles of baby oil in Diddy’s house during their raid earlier this year pic.twitter.com/R4OQLMQggx
— TheArmchairAnalyst (@Sitting_Analyst) September 18, 2024