Rosie O’Donnell Joked About Diddy’s Legal Drama 25 Years Ago

Back in the 1990s and early 2000s, Rosie O’Donnell spent a lot of time working on red carpets and chatting with other celebrities. Some of her early jokes are considered legendary. A clip from 2000 has recently resurfaced. Her joke wasn’t particularly funny, but it did seem to tell the future. Rosie O’Donnell once joked about Sean ‘Diddy’ Combs spending years in prison.

A clip of Rosie O’Donnell has gone viral as Diddy stands trial

Rosie O’Donnell made a little joke at the Grammy Awards 25 years ago that she probably hasn’t thought of since. The clip, however, is going viral. According to Page Six, O’Donnell joked with members of TLC about the nominees. Of the nominees, she said, “Lauryn Hill’s got four, TLC’s got eight, and Sean Combs five to ten.”

O’Donnell doubled down with the joke, saying, “I don’t mean to be mean, because, I mean, he’s a nice guy and he can really sing. Oops!” O’Donnell was referencing Sing Sing Correctional Facility, a maximum security prison in Ossining, New York, a town roughly an hour north of Midtown Manhattan. The facility has housed hitmen, members of organized crime families, and various other high-profile convicts over the years.

Did Rosie O’Donnell predict Diddy’s future?

While Rosie O’Donnell’s joke might seem like it predicted the future, the comedian’s quip didn’t materialize out of nowhere. O’Donnell was referencing previous legal drama for the music mogul. She made the joke in 2000, months after Diddy was arrested on gun charges following a shooting at a nightclub.

Diddy’s legal troubles for criminal possession of a weapon and bribing a witness hadn’t made it to the trial stage when O’Donnell made the joke. Still, his charges were well known. At the time, he was facing up to 15 years behind bars.

Diddy’s trial began in January 2001. He was acquitted in March 2001 after a seven-week trial. The rap mogul walked free and continued to produce music. Most of the crimes mentioned in the lawsuits filed against him happened after his 2001 legal squirmish.

How long could he spend in jail if found guilty now?

Rosie O’Donnell’s joke about Diddy finding himself in prison is poignant now. Still, the term she suggested is not even close to what the music mogul is currently facing. Diddy’s active criminal trial has much higher stakes than his 2001 weapons possession charge.

If a jury finds Diddy guilty on all charges in his ongoing federal trial, he faces between 15 years and life in prison. Both the sex trafficking and racketeering charges carry potential life sentences. His lesser prostitution charge carries a maximum sentence of 10 years.

Diddy is being held without bail at the Metropolitan Detention Center in Brooklyn. He has been at the institution since his arrest in September 2024. His trial will likely wrap up in late June. He’ll return to the detention center to await sentencing if he is found guilty. He would likely be transferred to a different federal lockup following sentencing. If found not guilty, he’ll walk free but will still have plenty of civil matters to attend to.