J. Lo made headlines with her relationship with then-rising rapper-mogul Diddy. But they weren't all good: On December 27, 1999, the couple was at a Manhattan club when gunfire erupted between Combs' crew and another group. Lopez and Combs were detained by police when a gun was found in the front seat of their vehicle. Lopez wasn't charged, and Diddy narrowly avoided conviction and prison time in a high-profile trial. The pair split a year later.