43. Michael Irvin
Criminal History: Felony cocaine possession
Time Behind Bars: N/A
Michael Irvin's been arrested a handful of times for drug possession. He reportedly split the lip of a referee during a charity basketball game. And in the why-isn't-this-a-more-famous-story segment of our show, famously mooned Gene Upshaw during an argument about player contracts.
But his most infamous incident involves a knife fight (doesn't it always?) over, of all things, a haircut. During Cowboy training camp in '98 Irvin claimed "seniority" in trying to split the line for a free buzz. When offensive linemen Everett McIver refused to budge from his spot, the two tussled resulting in a two-inch cut to McIver's neck that required eighteen stitches.