Rosie O’Donnell Cracked 2 Jokes About Diddy In 2000 That Make Way More Sense Today
Rosie O’Donnell is known for being funny, but her fortunetelling skills are clearly underappreciated.
In a resurfaced clip that’s currently getting attention on social media, the comedian can be seen telling jokes about Sean “Diddy” Combs going to jail two decades before his sex trafficking and racketeering arrest .
In 2000, O’Donnell was selected to host the Grammy Awards . To promote her gig, she showed a behind-the-scenes special on her now-defunct talk show “The Rosie O’Donnell Show” ahead of the awards ceremony.
In one segment from the special , O’Donnell hung out backstage with members of the R&B girl group TLC, which was nominated for multiple awards that year. The comedian decided to test out a few jokes she’d been working on with the band’s members, Lisa “Left Eye” Lopes, Rozonda “Chilli” Thomas and Tionne “T-Boz” Watkins.
“Wanna hear a joke I have?” O’Donnell asks the trio in the unearthed clip. “Ready? This is good. See if you like it.”
O’Donnell then tells this gem:
“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’ jaws drop and they immediately burst out laughing.
“Get it? Like, he’s going to jail?” O’Donnell continues, causing Thomas to laugh so hard that she hugs O’Donnell in appreciation.
But O’Donnell wasn’t done, telling the ladies she had an even better crack about the rapper up her sleeve.
“I don’t mean to be mean because, I mean, he’s a nice guy and he can really sing sing. Oops!” she says while covering her mouth.
All three women cackle in response to the quip that referenced Sing Sing Correctional Facility, a maximum-security prison in Ossining, New York.
It should be noted that O’Donnell was