Date: December 27, 1999
The Moment: At Club New York in Manhattan, just as the new millenium was about to arrive, the old one's hottest power couple of the moment—pop star/actress/erstwhile fly girl J-Lo and rapper/producer/media mogul Diddy—ducked out in the midst of total pandemonium after shots were fired in the club. And yes, there was a gun in the car that they left in.
The Impact: Diddy and J-Lo were arrested by the NYPD as the action unfolded, on account of that gun that was found in the 1999 Lincoln Navigator the duo tried to escape in with Diddy's bodyguard (much to the total, unrestrained glee of the tabloid press). Also, the fact that they ran through 11 red lights on their way may have helped speed the arrest process along.
Regardless: Jennifer Lopez was promptly let go, claiming no knowledge of the weapon that was in the car. Diddy, his bodyguard (Anthony Jones), his driver (Wardel Fenderson), and Jamal Barrows (better known as Shyne) were all charged, however. The first three got busted on account of the gun, which had been stolen from somewhere in Georgia a few months prior to the incident. Shyne, though, was charged with firing the bullets in the club (someone had said something not-so-nice to Diddy, and another had thrown a stack of cash). The tabloids had a field day with this for quite some time.
The Upshot: Diddy, with the help of superlawyer Johnnie Cochran, was acquitted of his charges (which included bribing his bodyguard to lie on his behalf), along with his bodyguard. Shyne went to jail for 10 years and emerged from prison only to be deported (as he's a naturalized citizen of Belize), and became an Orthodox Jew. Diddy and J-Lo broke up, and J-Lo moved on to a string of high-profile relationships (Ben Affleck, Marc Anthony) and high-profile career bombs (such as starring in Gigli with Ben Affleck).
Oh, and those three total bystanders who were shot? Diddy quietly settled their civil suit against himself and Shyne out of court, for a pretty six-figure sum.