For most people, a life of crime is a gamble. You'll either go on breaking the shit out of the law forever, or you'll get caught and go to jail. For some, however, there is a third option, one lined with money.
These people not only managed to have successful careers as criminals, but also turned their nefarious ways into legitimate profit after being arrested.
Danny Trejo: From Real Bad Guy to Movie Bad Guy
Danny Trejo is everyone's favorite terrifying Hispanic man.
This is not a publicity still. This is Danny going to Walgreen's.
Early on, Danny made a career out of robbing convenience stores, and eventually got addicted to drugs. The cops showed up at his house so much that his mom eventually said she stopped being surprised when they came. Then again she could have just taken one look at her son and guessed at his future.
Danny eventually earned himself 15 years in prison, including a stint in San Quentin. Determined to learn a valuable skill in jail, but presumably not one for poetry, he practiced boxing. He also embarked on a 12-step program that broke him of his addiction to drugs and alcohol.
"Glaring at addiction" was presumably the 12th step.
How Did He Turn it Around?
After his release, Trejo kept tabs on his former 12-step partners to help them stay on the straight and narrow. And, in one of those twists that makes a person believe in karma, one of those friends happened to be a production assistant for a movie called Runaway Train. Trejo was approached by a member of the movie staff and asked if he could look like a convict, which, of course, he could. In fact we're pretty sure that these days casting just asks if you can "Look like a Trejo."