5. Frank Sinatra

Could a mug shot look any cooler? The tussled pieces of hair. The “devil may care” look. The only thing cooler than a Frank Sinatra mugshot is two Frank Sinatra mugshots.

thesmokinggun.com

Ol’ Blue Eyes wasn’t always the smooth talking crooner. Even during his career, he had infamous bouts with the mafia. They even kidnapped his son. In 1938, however, Sinatra was just a young man who fell in love. He was arrested for “carrying on with a married woman”. That was actually a crime back in the day. By the look on Sinatra’s face, it seems like it was worth it.

metrolyrics.com

6. Charles and Nannie Hutchinson

The bond between mother and son is very strong. If you add murder, grave digging, and lying to the police into the mix, then that bond is solidified.

Nebraska State Historical Society

This mother and son duo, tried to pull off the perfect crime. Nannie was a maid for an Eli Feasel. She told Eli’s brother that he went to another state to see his son. After finding no trace of him, Eli’s brother became suspicious. The mother and son team were arrested, but later released without being formally prosecuted. A year later, a recently opened grave was discovered. Remains of Eli were discovered by a man who was working on the farm. After evidence was found that Nannie and Charles removed the remains, they were convicted of their crimes.

Nebraska State Historical Society