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Rosie O’Donnell Joked Diddy Was Going To Prison Over 20 YEARS Ago!

Rosie O’Donnell Joked Diddy Was Going To Prison YEARS Ago

Rosie O’Donnell has always had her guard up when it comes to Diddy!

The former talk show host has pointed words for the disgraced rapper — both past and present! Earlier this week, she took to TikTok to address the mounting drama surrounding Diddy and his sex trafficking and racketeering arrest. In the lengthy video, she reflects on her brief encounter with him years ago where she almost ended up at one of his parties!

She and her family showed up to what they believed was a casual New Years Eve party hosted by the Bad Boy Records founder. But they were NOT allowed in! The 62-year-old recalled:

“We didn’t know. We had on, like, sweatpants, me and my family and my kids. They didn’t let us in. The doormen were, like, looking at us. I’m like, ‘No, no. He invited me yesterday. I live right there. My daughter saw him on the street and we talked.’ No, we couldn’t come in.”

The question is, could they not come because of their attire? Or the fact they brought children??

Related: You Will NOT Believe What Diddy’s Lawyer Said About The 1,000 Bottles Of Baby Oil!!

She said the next day Diddy rented out a movie theater for her and her family to enjoy because he felt “so bad” about the mixup. Huh. Guess that was the family man side of him. Speaking of compartmentalizing, the comedian wondered aloud:

“I know that there’s perhaps a naivete to me in some way, but I think, how could a person live knowing that they had done that and then be a public person and continue to do it? Didn’t he feel, like, the footsteps of the law behind him at all times?”

She then went on to compare him to convicted rapist Harvey Weinstein:

“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.’”

You can watch her full TikTok (below):

@rosie

#pdiddy #trump #kamala #jdvance #nerflauncher #weinstein god help us ????????????????????????????????????????????????????????????????????????????????????????????????????????

♬ original sound – Rosie ODonnell

But how much “naivete” was really part of the equation? Because nearly 25 years ago, she joked he was going to prison!

In resurfaced footage circulating around social media, the A League of Their Own alum can be seen interviewing the TLC girls ahead of the 2000 Grammys, which she hosted. She says:

“Wanna hear a joke I have? Ready? This is good. See if you like it; Lot of multiple nominees, multiple Grammy nominees, this year. Lauryn Hill’s got four, TLC’s got eight and Sean Combs 5 to 10.”

Tionne “T-Boz” Watkins, Lisa “Left Eye” Lopes, Rozonda “Chilli” Thomas and all immediately began laughing while displaying shocked expressions. Rosie adds:

“Get it? Like, he’s going to jail? I don’t mean to be mean because, I mean, he’s a nice guy and he can really sing sing. Oops!”

Wow! Watch for yourself (below):

Oof!

Why did she think he was going to prison at the time if NOT for the party stuff? Maybe it was the whispers about his alleged involvement in Tupac‘s death?

But with Diddy now currently in jail, that joke just got a whole lot louder, that’s for sure…

Thoughts, Perezcious readers??

[Images via NBC & Vogue/YouTube]

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Sep 26, 2024 16:18pm PDT