By the late nineties, Diddy, then know as Puff Daddy, had already endured his share of scandals, mixed with massive success. After thriving as an intern-turned-executive at Uptown Records, he jumped shipped to start his own label, Bad Boy, which launched countless hip-hop stars. Diddy also found fame as a rapper, and was soon wildly partying in Hollywood, the Hamptons, and St. Tropez. Bad Boy’s growing rivalry with West Coast label Death Row exploded with the 1997 shooting of Biggie Smalls. It seemed as if Biggie’s tragic death (and that of Tupac Shakur) would inspire Diddy to finally drop the drama and settle down.
Instead, he hopped in bed with bombshell Jennifer Lopez, who was quickly rising to the top of the tabloids as a talented triple-threat. On December 27, 1999, the pair was out at Club New York in Manhattan with Diddy’s crew, when gunfire broke out. The mogul, along with his then-protégé Shyne, was arrested after his driver turned him in, accusing his boss of attempting to bribe him into taking the weapon used in the shooting. The seven-week trial in 2001 hogged headlines across the country. Diddy, obviously exhausted, was shaking as the jury handed down their decision: acquittal. (Shyne‘s fate wasn’t nearly as blessed; he was found guilty of weapons charges and assault, and landed in jail.)
Diddy later declared that the two-year ordeal had “made me deeper.” It also turned him back into a single man — he and J. Lo parted ways a few weeks later.