1. Billy the Kid
Billy the Kid, born Henry McCarty, was the ultimate teenage outlaw. He was charming, quick with a revolver, and supposedly killed his first man at just 15. By his death at 21, he had racked up a body count of at least eight men—though legends love to inflate the numbers. His most famous escape came in 1881 when he broke out of jail, killing two deputies on his way out. Billy’s reputation for being a wild but almost mythical gunslinger made him the stuff of folklore. Pat Garrett finally brought his rampage to an end, but Billy’s legend continues to loom larger than life.
2. Jesse James
Jesse James wasn’t just a train robber; he was practically a folk hero. After the Civil War, Jesse and his brother Frank took their Confederate bitterness and turned to a life of crime, robbing banks, trains, and stagecoaches. What made Jesse so chilling was his precision—he was always calculated but ruthless when needed. His gang became infamous for robberies that struck terror across the Midwest. Despite his violent streak, stories of him giving back to the poor earned him a Robin Hood-like reputation. His betrayal came in 1882 when a member of his own gang shot him in the back for the reward money.
3. Belle Starr
Belle Starr, known as the “Bandit Queen,” defied the notion that the Old West was a man’s world. She ran with infamous gangs like the James-Younger Gang and later turned to cattle rustling and horse theft. Belle had a knack for staying one step ahead of the law, often using her charm and wit to escape capture. Her flair for dressing in fancy velvet gowns and riding sidesaddle with a pistol on her hip only added to her mystique. Belle met a violent end in 1889 when she was ambushed and shot, leaving behind a legacy as one of the West’s most dangerous women.
4. Butch Cassidy
Butch Cassidy, leader of the Wild Bunch, was the brains behind some of the most successful robberies of his time. Alongside his partner, the Sundance Kid, he robbed banks and trains with a mix of charm and criminal ingenuity. Despite his outlaw lifestyle, Cassidy was said to dislike violence, preferring to get in and out with as little bloodshed as possible. However, he was always ready to fight if needed, and the Pinkertons chased him for years. Legend has it he fled to South America to escape the law, where his fate remains a mystery to this day.
5. The Sundance Kid
The Sundance Kid, born Harry Longabaugh, was Butch Cassidy’s right-hand man and one of the fastest guns in the West. Though quieter and more stoic than Cassidy, Sundance had a reputation for being deadly accurate with a revolver. His skills made him a key member of the Wild Bunch, specializing in train heists. He and Cassidy’s escape to South America added an air of mystery to their legend—did they die in a shootout, or did they disappear into obscurity? Either way, Sundance remains one of the sharpest and most feared outlaws of the Old West.
6. John Wesley Hardin
John Wesley Hardin might’ve been the scariest of them all—because he truly enjoyed killing. By his own account, he killed more than 40 men, starting at the age of 15. Hardin didn’t discriminate, killing lawmen, gamblers, and anyone who crossed him. Once, he allegedly shot a man just for snoring too loudly. His sharp temper and unmatched skill with a gun made him a walking death sentence. Captured at last in 1877, he spent 17 years in prison but met his end soon after release—shot in the back during a card game.
7. Wyatt Earp (The Lawman-Turned-Outlaw)
While Wyatt Earp is often remembered as a lawman, his actions at the O.K. Corral and beyond earned him a reputation for being ruthless. Earp was no stranger to bending the law, taking bribes, and engaging in vigilante justice when it suited him. After his brother Morgan was killed, Wyatt led a bloody vendetta, gunning down anyone he believed responsible. Though technically on the side of “law and order,” his methods were brutal and unrelenting. Wyatt Earp blurred the lines between hero and villain, proving that justice in the Old West was often served at the end of a gun.
8. Black Bart
Black Bart, the gentleman bandit, had a style all his own. Unlike most outlaws, he hated violence and carried an unloaded shotgun during his robberies just to make a show of things. Bart made a name for himself robbing stagecoaches across California, often leaving behind poetry to taunt the authorities. His wit and refusal to harm his victims made him a peculiar figure in the Old West. When he was finally caught in 1883, his capture marked the end of an era—proof that even the most charismatic outlaws couldn’t escape justice forever.
9. Doc Holliday
Doc Holliday wasn’t just a dentist—he was one of the deadliest gunfighters in the West. A friend of Wyatt Earp, Doc’s loyalty led him to the infamous O.K. Corral shootout, where his fast draw became legendary. Despite suffering from tuberculosis, Doc fought as though he had nothing to lose, making him unpredictable and dangerous. His combination of wit, charm, and deadly accuracy with a six-shooter made him a feared opponent. Though he didn’t live to see old age, Doc Holliday cemented himself as one of the most fearsome figures of the Old West.
10. Clay Allison
Clay Allison was the definition of a wild, unhinged gunslinger. Known for his erratic behavior, he once reportedly danced naked on a table while firing his revolvers in the air. Allison didn’t shy away from violence, often settling disputes with his gun instead of words. One of his most notorious acts was decapitating a man and displaying the head as a warning. Stories of his exploits made him a legend of the Old West, though his unpredictability made him as dangerous to friends as he was to enemies.
11. Sam Bass
Sam Bass started as a small-time thief but quickly became one of the most notorious stagecoach and train robbers in Texas. Known for his daring heists, Bass had an uncanny ability to escape lawmen, earning him a reputation as a slippery and cunning outlaw. His most famous score came in 1877 when he and his gang stole $60,000 in gold coins—an enormous haul for the time. However, his luck ran out when Texas Rangers ambushed him, leading to his death in a bloody shootout. Bass’s short but thrilling career cemented his place in outlaw history.
12. Bill Doolin
Bill Doolin, leader of the infamous Doolin-Dalton Gang, made his mark robbing banks, trains, and stagecoaches across the frontier. Doolin was as ruthless as he was clever, known for organizing carefully planned heists. After several bloody shootouts with lawmen, he became one of the most wanted men in the West. The chase ended in 1896 when a posse tracked him down and shot him dead. Despite his grim end, Doolin’s reputation as a master criminal and sharpshooter continues to haunt the legends of the Wild West.
