‘She Knew What Was Up’: Fans Say Rosie O’Donnell’s 2000 Quip About Her Then-Neighbor Diddy’s Alleged Crimes Feels Like a Prophecy Amid His New Legal Woes 

Jokes about Sean “Diddy” Combs’ wild lifestyle have been floating around Hollywood for years, but one resurfaced clip from 2000 now feels eerily prophetic given his recent legal issues. Rosie O’Donnell’s quip about Diddy’s potential prison time, made more than two decades ago, has fans raising their eyebrows in light of his September arrest. A resurfaced clip of comedian Rosie O’Donnell seems to show her predicting his eventual incarceration. (Photos: Rosie O’Donnell @chattingjason (JasonChatting) Wiki Commons Media, @diddy/Instagram) A resurfaced video from “The Rosie O’Donnell Show,” which has gone viral thanks to a repost from “Entertainment Tonight,” features O’Donnell alongside Lisa “Left Eye” Lopes, Rozanda “Chilli” Thomas, and Tionne “T-Boz” Watkins of TLC during a pre-Grammy interview. As the group chatted, O’Donnell couldn’t resist poking fun at Combs, who was entangled in legal troubles at the time. She joked, “A lot of multiple nominees, multiple Grammy nominees this year. Lauryn Hill’s got 4, TLC’s got 8, and Sean Combs 5 to 10.” O’Donnell then added, “He can really sing sing,” a clever reference to the notorious maximum-security prison in Ossining, New York. The TLC trio burst out laughing at O’Donnell’s sharp humor, showing that even back then Combs’ legal woes...