23. Richard Speck
Richard Speck lived a dark, nomadic life. An experienced seaman, the Illinois native jumped from ship to ship working odd jobs, but in July 1966, a lack of sufficient employment sent him to a Chicago-area tavern, where he started drinking the pain away. Liquored up, Speck held a 53-year-old woman, Ella Mae Hooper, up at knifepoint, forced her into his Shipyard Inn room, raped her, and left with her .22 caliber pistol. Dressed in all-black, he returned to the bar for more drinks and eventually left with Hooper's gun and a switchblade, walked a mile and a half, and decided to break into a townhouse.
As it turned out, the townhouse was actually a dormitory housing young nursing students. Speck's own account suggests that he was high out of his mind and possibly only wanted to rob the place, but the incident played out far more horribly. He kept the women prisoner in their home, leading them out of a room one at a time, killing them through stabbing or strangulation, and even raping one of them before strangling her to death.
One woman, however, managed to hide under a bed for seven hours, and her escape—as well as someone recognizing Speck's "Born To Raise Hell" tattoo while he was in a hospital after a suicide attempt—ultimately led to his apprehension and jail sentence. He served 24 years in prison before of dying of natural causes.