Though a handful of stars have managed to make crime look cool — case in point, the now-iconic mugshots of folks like David Bowie and Frank Sinatra — a trip to jail was more than just mean mugging for the camera. It meant having to deal with some really scary perps.  

From a woman's saucer-like pupils to a convict held in a headlock, here are 21 old-school mugshots from people you would not want to share a cell with.