Rosie O’Donnell Cracked 2 Jokes About Diddy In 2000 That Make Way More Sense Today

Rosie O’Donnell is known for being funny, but her fortunetelling skills are clearly underappreciated.

In a resurfaced clip that’s currently getting attention on social media, the comedian can be seen telling jokes about Sean “Diddy” Combs going to jail two decades before his sex trafficking and racketeering arrest.

In 2000, O’Donnell was selected to host the Grammy Awards. To promote her gig, she showed a behind-the-scenes special on her now-defunct talk show “The Rosie O’Donnell Show” ahead of the awards ceremony.

In one segment from the special, O’Donnell hung out backstage with members of the R&B girl group TLC, which was nominated for multiple awards that year. The comedian decided to test out a few jokes she’d been working on with the band’s members, Lisa “Left Eye” Lopes, Rozonda “Chilli” Thomas and Tionne “T-Boz” Watkins.

“Wanna hear a joke I have?” O’Donnell asks the trio in the unearthed clip. “Ready? This is good. See if you like it.”

O’Donnell then tells this gem:

“Lot of multiple nominees — multiple Grammy nominees — this year. Lauryn Hill’s got four, TLC’s got eight and Sean Combs 5 to 10.”

Lopes’ and Thomas’ jaws drop and they immediately burst out laughing.

“Get it? Like, he’s going to jail?” O’Donnell continues, causing Thomas to laugh so hard that she hugs O’Donnell in appreciation.

But O’Donnell wasn’t done, telling the ladies she had an even better crack about the rapper up her sleeve.

“I don’t mean to be mean because, I mean, he’s a nice guy and he can really sing sing. Oops!” she says while covering her mouth.

All three women cackle in response to the quip that referenced Sing Sing Correctional Facility, a maximum-security prison in Ossining, New York.

It should be noted that O’Donnell was likely referring to Combs’ public legal problems before 2000, which included a 1996 misdemeanor criminal mischief charge for threatening a photographer with a gun, and a woman’s claim that Combs shot her at a New York City nightclub in 1999.

HuffPost has reached out to O’Donnell for clarity about the motivations behind her 2000s jokes about Combs.

In a recent TikTok, O’Donnell expressed surprise about Combs’ sex trafficking and racketeering indictment and said she used to be neighbors with him in Miami.

“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 said.

She explained that because she was unaware of the dress code, she and her family — including her kids — showed up to the notorious bash wearing sweatpants. O’Donnell said that they were turned away at the door.

The next day, the comedian said, she got a call from Combs telling her that he felt “so bad” about her being rejected at the door that he rented out a Regal Cinema “for me and my family to see any movie we want the entire day in any theater whenever we wanted.”

Calling the apology gift “so unbelievably over the top and extraordinary,” O’Donnell said that although she never spoke to Combs again after that day, it left her with a positive impression.

“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.’”

Combs pleaded not guilty last week to the charges against him.