When: 1999 - 2001
Jennifer Lopez and Puffy were tabloid royalty and one of the greatest celebrity power couples OF ALLLL TIIIIIME! Their appearance at the 2000 Grammy Awards was the pinnacle of their flamboyance, due in large part to J. Lo’s now-iconic green dress. But a nightclub shooting at Club New York in December 1999 put a strain on their relationship. Puff recently admitted in a Playboy interview that the publicity around the ensuing trial put a wedge between him and Jenny from the block, plus Kim Porter was still in the picture at the time. The couple would eventually break up (on Valentine’s Day no less!) shortly before Puff was acquitted in 2001 on all charges stemming from the shootout. Their relationship is ancient history at this point, but Puff still did bang one of the baddest chicks ever—in the prime of her hotness—so it’s only right he still stunts about it in 2010, spitting lines like, “I don’t fuck with fake hoes, all I touch is J-Lo’s!” Gangsta!
Smash Probability: