The Date: November 2006
The Fail: Williams was arrested at Los Angeles International Airport after authorities found a stolen gun in a briefcase he was carrying.
Our Reaction: Carrying a handgun through an airport—or, rather, trying to carry a handgun through an airport—never made any sense to us. Does this ever work? Like, whether you're a celebrity or not, are that many people really sneaking gats onto planes? Either way, this was a dumb thing for Williams to do at the beginning of his career and the first of many legal problems to come.