Year Arrested: 1972

Crime: Driving while intoxicated.

When you charged through life fueled by booze, women, and fast cars, you're going to have your fair share of conflicts with the law. Steve McQueen, known as The King of Cool and for his anti-hero image, was arrested for drunken driving in Anchorage, Alaska, and he didn't seem to give one single fuck about it. That shirt is fire, but his cavalier attitude is what makes this an incredibly stylish mugshot.