A gangster of the Great Depression era, John Dillinger led a group known as the "Dillinger Gang". His gang was accused of robbing 24 banks and four police stations. He was a master evader and escaped the police’s attempts to capture him many times. He was finally shot to death by the authorities in 1934.
Israel Keyes was a serial killer, rapist, and burglar, who had killed at least three people. He previously owned a construction business and had served the U.S. army. Israel was fond of Ted Bundy and committed suicide while awaiting trail in the case related to the murder of Samantha Koenig.
Charles Harrelson was a hitman who was convicted of assassinating John H. Wood Jr., a U.S. federal judge. Harrelson was the father of Woody Harrelson, who became an actor later, though Harrelson mostly remained estranged from his son. Harrelson's story inspired the 10-episode podcast Son of a Hitman.
Train and bank robber Butch Cassidy was the leader of a gang of criminal outlaws known as the "Wild Bunch" in the Old West. The son of ranchers, he ran away from home as a teenager and became involved in a life of crime. He started with minor criminal offenses and eventually became a much-feared robber.
Baby Face Nelson was an American bank robber. He gained notoriety during the early and mid-1930s for leading his own gang and carrying out organized crime, such as bank robbery. He was responsible for killing many FBI agents and was killed in a furious gun battle called The Battle of Barrington. His life inspired many films, including Baby Face Nelson.