A joke made by Rosie O’Donnell almost 25 years ago has taken on new significance, as Diddy now faces serious legal charges in 2024. The viral moment comes from a 2000 interview where O’Donnell made a comment about Diddy’s legal troubles amid his involvement in a nightclub shooting. During the segment, O’Donnell quipped, “A lot of multiple nominees this year: Lauryn Hill’s got four, TLC’s got eight, and Shan Coles 5 to 10—he’s going to jail, right?”
At the time, Diddy had not been cleared of charges related to the incident, but O’Donnell’s joke about him potentially going to prison now seems eerily prescient in light of Diddy’s current legal issues.
As if the joke wasn’t enough, the resurfaced moment comes alongside other reappearing stories about Diddy’s past, including a 2015 interview with Jennifer Lopez on The Wendy Williams Show, where Lopez’s mother, Guadalupe, commented on the possibility of JLo rekindling a romance with Diddy, adding humorously, “I could always see you getting back with Puffy in a little way. I mean, he’s a nice guy and he can really sing, sing—oops.”
These old clips are now circulating again, offering a new perspective on Diddy’s troubled past, as he faces charges of racketeering, sex trafficking, and more in 2024.
