Last Updated on September 29, 2025 by Matt Staff
History books and Hollywood movies have given us a romanticized image of outlaws, rebels with guns, fast horses, and even faster reputations. But beyond the legends, there are surprising, quirky, and little-known stories about these infamous figures. These tales about famous outlaws reveal the human side of some of history’s most notorious lawbreakers.
1. Jesse James loved to read
Behind his reputation as a ruthless bandit, Jesse James was an avid reader of Shakespeare and reportedly quoted passages to his gang.
2. Billy the Kid’s soft spot for orphans
Though portrayed as cold-blooded, Billy the Kid often spared orphans and widows when raiding towns, leaving food and supplies behind.
3. Belle Starr rode sidesaddle to show off
The “Bandit Queen” preferred riding sidesaddle in full skirts, part practicality, part theater to keep her infamy alive.
4. Butch Cassidy, the Bank Customer
Before robbing banks, Cassidy opened accounts at some of them under his real name, charming tellers and studying layouts.
5. The Sundance Kid was a Skilled Carpenter
Harry Longabaugh (the Sundance Kid) supported himself between robberies by building furniture and repairing barns.
6. John Dillinger’s Movie Star Dreams
Dillinger idolized swashbuckling actor Douglas Fairbanks and even mimicked his mannerisms while on the run.
7. Pretty Boy Floyd Paid Off Debts
Known as a “Robin Hood” outlaw, Floyd reportedly tore up mortgage papers during bank heists to free farmers from debt.
8. Ma Barker Was More of a Mascot
Though depicted as the mastermind of the Barker gang, historians argue that Ma Barker had little control over the actual crimes.
9. Ned Kelly’s Homemade Armor
Australia´s most famous outlaw built his own steel armor out of plow parts, weighing over 90 pounds.
10. Clyde Barrow’s Saxophone
When not robbing banks with Bonnie Parker, Clyde played the saxophone, a hobby he picked up in reform school.
11. Bonnie Parker was a Poet
Before becoming part of the Bonnie & Clyde legend, she wrote dozens of poems about her life, dreams, and regrets.
12. Joaquin Murrieta’s Mythic Identity
California´s “Robin Hood” outlaw may have been multiple men whose deeds merged into one legendary figure.
13. Black Bart the Polite Stagecoach Robber
Bart left behind poetry at the scene of his stagecoach robberies, signing them “Black Bart, the P o 8.”
14. Sam Bass’s Generosity
Bass, a Texas outlaw, once gave stolen money to a destitute family he encountered on the road.
15. Doc Holliday’s Dental Practice
Before becoming Wyatt Earp´s infamous ally at the O.K. Corral, Doc Holliday was a trained dentist with a promising career.
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These 15 stories show that famoys outlaws weren´t just one-dimensional villains. They were musicians, readers, poets, and sometimes reluctant criminals, people whose real lives were stranger, and often more fascinating, than the myths we´ve inherited. If you loved this content, check out 28 Clever Comebacks We Wish We Had Thought Of, or 17 Last Known Photos of Notorious Outlaws.
