Skip to content
Search AI Powered

Latest Stories

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

Rosie O'Donnell; Sean 'Diddy' Combs
@TheTLCVault/X, TAO Group Hospitality/GettyImages

The actor was hosting the 2000 Grammy Awards when she cracked two jokes about the rapper going to prison to the R&B group TLC in a behind-the-scenes video.

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.

@rosie

#pdiddy #trump #kamala #jdvance #nerflauncher #weinstein god help us đŸ‡ș🇾đŸ‡ș🇾đŸ‡ș🇾đŸ‡ș🇾đŸ‡ș🇾đŸ‡ș🇾đŸ‡ș🇾đŸ‡ș🇾đŸ‡ș🇾đŸ‡ș🇾đŸ‡ș🇾đŸ‡ș🇾đŸ‡ș🇾


“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 naĂŻvetĂ© 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.

More from Entertainment/music

Jesse Watters
Fox News

Jesse Watters Dragged After Adding Another Mind-Boggling Rule For 'Real Men'

Fox News host Jesse Watters, who is apparently an authority of what it means to be a manly man, gave jazz hands to make a point about how "real men" should or shouldn't wave.

The target of his ridicule was Tim Walz, the enthusiastic Democratic Minnesota governor and vice presidential candidate who often greets the public by raising both hands in the air to wave.

Keep ReadingShow less
Screenshots of crowd at town hall and Rep. Mike Flood
@MorePerfectUS/X; KETV NewsWatch 7

GOP Rep. Goes Viral For His Response To Crowd Chanting 'Tax The Rich' At Town Hall

Nebraska Republican Representative Mike Flood was criticized following his incredulous response to a crowd that chanted "Tax the rich!" during a town hall meeting.

The Columbus High School auditorium hosted the town hall on Tuesday evening, drawing "nearly 380" attendees, according to local network KETV Omaha. The event was lively, with Flood facing both sharp criticism over Trump administration policies and some appreciation for showing up in person.

Keep ReadingShow less
Elon Musk
Andrew Harnik/Getty Images

Awkward Typo In Elon Musk's Bizarre 'Education Department' Trump Meme Is A Total Self-Own

Billionaire Elon Musk was widely mocked after he celebrated President Donald Trump's executive order to begin to dismantle the Department of Education (DOE) by posting a meme of Trump at the department's grave, only for an awkward misspelling to get all the attention.

Polling indicates that eliminating the Education Department is largely unpopular, with 60% of registered voters opposing the move, according to a Quinnipiac University survey conducted March 6-10. Support stands at 33%, with opposition particularly strong among Democrats—98% oppose it, while just 1% support it.

Keep ReadingShow less
JB Pritzker; Donald Trump
Jacek Boczarski/Anadolu via Getty Images; Anna Moneymaker/Getty Images

Dem Governor Reveals Trump's Bonkers Demand In Exchange For Equipment During COVID

Illinois Democratic Governor J.B. Pritzker revealed during a speech this week that he clashed with President Donald Trump during the first Trump administration after Trump promised necessary medical equipment during the COVID pandemic on the condition that Pritzker praise him publicly.

Five years ago, the United States was grappling with the initial impacts of the COVID-19 pandemic. The country had entered shutdowns that had severe economic consequences, leaving businesses and industries on the brink of collapse.

Keep ReadingShow less
Scrabble tiles spelling the word scam
Scam spelled with scrabbles on a wooden table

People Break Down How They Realized An Entire Industry Was A Total Scam

We unfortunately live in a world where scams are on the rise.

Thankfully, some of them are pretty easy to detect, such as an automated call from the IRS telling you a warrant is out for your arrest, or an email claiming to be from Amazon or the USPS asking for your credit card information, only to look closer and see the email address is a yahoo account.

Keep ReadingShow less