Amy Winehouse – Musician Mug Shots
Busted time and time again for various drug offenses, by the time of this 2008 arrest on suspected drug possession, Amy Winehouse had gone over the deep end. Sad displays like the face she's making in this mug shot were more common as she seemed to be carving a path of destruction. In fact, we can't even determine which specific arrest this stems from. Of course, we all know how this one turned out.