Rosie O’Donnell joked Sean ‘Diddy’ Combs was going to jail years before rapper’s arrest: He will get ‘5 to 10’

A clip of Rosie O’Donnell joking that Sean “Diddy” Combs would one day serve “5-10” years in jail has resurfaced amid the Bad Boy Records founder’s mounting legal woes.

The former talk show host poked fun at Combs potentially being locked up as she appeared in a video with TLC members Tionne “T-Boz” Watkins, Lisa “Left Eye” Lopes and Rozonda “Chilli” Thomas ahead of the 2000 Grammys.

“Wanna hear a joke I have? Ready? This is good. See if you like it,” O’Donnell began, per a clip shared on X.

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

A clip of Rosie O’Donnell joking about Sean “Diddy” Combs going to jail has resurfaced in light of the music mogul’s recent legal woes. RunninMyMouf/TikTok Prior to the 2000 Grammy Awards, O’Donnell joked with TLC that Combs would serve “5-10” years behind bars. RunninMyMouf/TikTok

The wisecrack evoked chuckles from Lopes and Thomas before their expressions turned to shock.

“Get it? Like, he’s going to jail?” O’Donnell clarified, more than two decades before the rapper’s sex trafficking arrest.

“I don’t mean to be mean because, I mean, he’s a nice guy and he can really sing sing. Oops!” she added, referring to the New York-based prison.

“I don’t mean to be mean because, I mean, he’s a nice guy and he can really sing sing. Oops!” O’Donnell quipped, referring to the New York-based prison. Getty Images The former talk show host also addressed Combs’ arrest on TikTok and compared him to Harvey Weinstein, who was arrested on rape and sexual abuse charges in 2018. TikTok/@rosie

O’Donnell, who was Combs’ neighbor at one point, spoke out about the music mogul’s arrest on TikTok earlier this week and she compared the record producer to Harvey Weinstein, who was arrested on rape and sexual abuse charges in 2018.

“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 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,'” she wondered aloud.

The comedian then asked how Combs would not “consider [himself] a rapist” despite allegedly “participating in or filming or watching the rape,” according to allegations in his indictment.

Combs was arrested on Sept. 16 in Manhattan and charged with racketeering conspiracy, sex trafficking and transportation to engage in prostitution. Getty Images for Sean "Diddy" Combs Prosecutors claim the 54-year-old record producer “abused, threatened and coerced women and others around him to fulfill his sexual desires, protect his reputation and conceal his conduct” for decades. Getty Images

“It’s very disturbing,” she said. “And then you start to think, how many people really knew about it?”

Combs was arrested on Sept. 16 in New York City. The following day, it was revealed he was being charged with racketeering conspiracy; sex trafficking by force, fraud or coercion; and transportation to engage in prostitution.

Prosecutors claim that the 54-year-old rapper “abused, threatened and coerced women and others around him to fulfill his sexual desires, protect his reputation and conceal his conduct” for decades, per the indictment.

They also accuse him of “creating a criminal enterprise whose members and associates engaged in … sex trafficking, forced labor, kidnapping, arson, bribery and obstruction of justice.”