Clip Of Rosie O'Donnell Jokingly Predicting Diddy Would Go To Prison Resurfaces After His Arrest

A vintage clip of comedian Rosie O'Donnell joking that rapper Sean "Diddy" Combs was going to prison has resurfaced following news of his indictment last week on federal sex trafficking and racketeering charges.

In 2000, O'Donnell promoted her gig as host of that year's Grammy Awards ceremony by sharing clips of her backstage on her former eponymous talk show.

One segment from the clip now from over two decades ago showed O'Donnell hanging out with TLC, the 1990s R&B girl group, which was composed of Tionne "T-Boz" Watkins, Lisa "Left Eye" Lopes, and Rozonda "Chilli" Thomas.

O'Donnell asked TLC, who were nominated for multiple awards that year, if they wanted to "hear a joke" she had and if they were ready for it. She promised, "This is good. See if you like it."

When she got their full attention, O'Donnell said:

“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 gave into fits of laughter from O'Donnell pushing the envelope, as she always had.

The comedian continued, for all the folks watching who were still in the dark about the prison term reference, "Get it? Like, he’s going to jail?”

Thomas, who still had her hand over her mouth from the joke continued laughing and went in for a hug with the bold comedian.

Here is the resurfaced clip.

O'Donnell went further, saying:

“I don’t mean to be mean because, I mean, he’s a nice guy and he can really sing, sing. Oops!”

The clip ended with the women cracking up at O'Donnell's reference to New York's maximum security prison, Sing Sing Correctional Facility.

Jaws were also dropping online.

O'Donnell had clarified with the Huffington Post that her joke was aimed at Diddy being tied to a New York City nightclub shooting incident on December 27, 1999.

A woman named Natalia Reuben claimed she saw the rapper with a gun and he shot at her.

Actor Jennifer Lopez, who was dating Diddy at the time, was reportedly with him on the night of the shooting.

O'Donnell explained at the time of her hosting the Grammys that “The JLo and P Diddy club shooting had just happened” and “there was speculation that he was going to jail for that event, hence the jokes.”

In the email she sent to the media outlet, O'Donnell said JLo had reached out and asked her not to make any jokes related to the shooting but "did them anyway."

She added that she “never thought [Combs] was a criminal sexual abuser never mind sex trafficking accusations." O'Donnell said she “thought he was a tough guy with a gun.”

In a recent TikTok video, O'Donnell expressed being taken aback after discovering the legal troubles facing Diddy, who used to be her neighbor 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," said O'Donnell about her and her kids not being aware of the dress code and showing up in sweatpants.

They were subsequently turned away at the door for not getting the memo.

The comedian said Diddy called her the next day after feeling guilty about how things went down at his posh party that he made it up to her by renting out a Regal Cinema " for me and my family to see any movie we want the entire day in any theater whenever we wanted.”

His thoughtful gesture stayed with her even though they hadn't spoken much since then.

O'Donnell said she was "in shock" over Diddy's indictment, saying:

“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.’”

Last week, Diddy was indicted by the federal grand jury in Manhattan and charged with sex trafficking, racketeering, and the "creation of a criminal enterprise in which he abused, threatened, and coerced women and others around him to fulfill his sexual desires, protect his reputation, and conceal his conduct."

Diddy denied the charges and is being held without bail.