1. Billy the Kid
Billy the Kid, born Henry McCarty, is often considered one of the most iconic outlaws of the Old West. Known for his youthful bravado, he supposedly killed his first man at just 15 and went on to become a feared gunslinger. By the time he was killed at 21, his body count was likely far fewer than the 21 kills often attributed to him, but his reputation only grew over time, according to Britannica. His famous escape from jail in 1881, where he shot and killed two deputies, cemented his status as a fugitive hero.
Though his criminal activities included cattle rustling and robbery, Billy’s charm and resourcefulness made him a symbol of rebellious youth. He was eventually gunned down by Sheriff Pat Garrett, who had been on his trail for years. However, the stories surrounding his death, including the possibility of him faking his own demise, have kept his legend alive. Whether a true outlaw or a misunderstood figure, Billy the Kid’s story is one that will forever be shrouded in myth.
2. Jesse James
Jesse James was more than just a criminal—he became a symbol of resistance for many in the post-Civil War era, PBS explains. A former Confederate soldier, Jesse turned to robbing banks, trains, and stagecoaches, initially out of bitterness towards the Union. He was meticulous in planning his heists, making sure his gang was always one step ahead of the law. The James Gang struck terror across the Midwest, but Jesse’s somewhat charitable actions towards the poor earned him a “Robin Hood” image.
In 1882, Jesse’s life came to a tragic and ironic end when a member of his own gang, Robert Ford, shot him in the back for the reward money. His death marked the end of a legendary outlaw career, but his story still captivates the public imagination. Over the years, various films and books have glorified his life, turning him into a tragic figure whose rebellion was against a nation that he felt had turned its back on him. Despite his violent nature, Jesse James remains one of America’s most legendary outlaws.
3. Belle Starr
Belle Starr, often dubbed the “Bandit Queen,” broke all stereotypes of women in the Old West. Born into a wealthy family, she eventually turned to crime, becoming involved with notorious gangs, Humanities Texas explains. Known for her beauty and charm, Belle ran cattle rustling and horse theft rings, often evading capture through her intelligence and connections. She became a symbol of a woman who wasn’t afraid to live on her own terms, even in a man’s world.
Her daring lifestyle caught up with her in 1889 when she was ambushed and shot in the back while riding home from a visit to her family. The details surrounding her death remain unclear, with some theories suggesting it was a result of personal vendettas, while others believe it was the result of her outlaw activities catching up with her. Belle’s legacy lives on as a woman who carved her place in a dangerous world and became an icon of female outlawry.
4. Butch Cassidy
Butch Cassidy, the leader of the Wild Bunch, was a criminal mastermind with a reputation for planning daring heists, Britannica explains. Along with his partner, the Sundance Kid, Butch robbed trains and banks across the West with calculated precision. His charm and keen sense of strategy helped him evade capture for years, making him one of the most successful outlaws of his time. Despite his violent profession, Butch was known for avoiding unnecessary bloodshed, preferring to get in and out as quickly as possible.
Butch’s legend grew after he and Sundance fled to South America to escape law enforcement, and their ultimate fates remain clouded in mystery. Some believe they were killed in a shootout, while others think they lived out their lives in obscurity. His life became a symbol of the ultimate escape, leading to numerous books and films that turned him into an enduring figure of the Old West. Whatever the truth, Butch Cassidy remains one of the most intriguing outlaws in American history.
5. The Sundance Kid
Harry Longabaugh, better known as the Sundance Kid, was the quiet but deadly partner of Butch Cassidy. Though not as flamboyant as Butch, Sundance was a sharpshooter with incredible accuracy, making him an invaluable member of the Wild Bunch, according to Cowboy State Daily. His skill with a revolver made him feared across the West, but unlike many of his counterparts, he preferred a life of minimal violence. His partnership with Butch in South America added an air of mystery to his legacy—did they die in a final shootout, or did they vanish forever?
The lack of concrete evidence about his death has only added to the myth of the Sundance Kid. What’s certain is that his partnership with Butch made them one of the most legendary outlaw duos in American history. Despite his quiet demeanor, his deadly skills and mysterious end have kept his story alive, cementing him as one of the West’s most feared and fascinating figures.
6. John Wesley Hardin
John Wesley Hardin was not only infamous for his criminal activities but also for his complete lack of restraint when it came to violence. Claiming to have killed more than 20 men by the time he was in his early 20s, Hardin was known for his quick temper and deadly aim. He killed his first man at just 15 years old and didn’t stop there, taking down lawmen, gamblers, and anyone who crossed him. His most notorious story involves killing a man just for snoring too loudly in his presence.
Hardin’s violent ways eventually caught up with him when he was captured in 1877 and sentenced to prison for several years. After his release, he tried to go straight, but his life was cut short when he was shot in the back during a card game in 1895. Despite his brutal career, Hardin remains one of the most infamous gunmen in the history of the Old West, a man who lived by the revolver and died by it.
7. Wyatt Earp (The Lawman-Turned-Outlaw)
Wyatt Earp is often remembered as a legendary lawman, but his life was filled with shades of gray. He became famous for his role in the infamous O.K. Corral shootout, but his actions often blurred the lines between lawman and outlaw. Earp had a reputation for taking matters into his own hands, as seen when he sought bloody vengeance after the death of his brother Morgan. His methods of justice, though often brutal, earned him a place in history, but they also left a legacy of violence and revenge.
While his career as a lawman is celebrated, Earp was also known to engage in questionable activities, such as gambling and even working as a saloon keeper. His time in Dodge City and Tombstone made him a hero to some and a villain to others. Earp’s complex nature and his ruthless pursuit of justice, regardless of the cost, make him one of the most fascinating figures of the Old West.
8. Black Bart
Black Bart, the “gentleman bandit,” stood out in the world of outlaws for his style and lack of violence. He was a notorious stagecoach robber who became famous for his poetic flair, often leaving behind handwritten verses after his heists. Unlike most outlaws of the time, Bart would rob stagecoaches without ever firing a shot, carrying an unloaded shotgun to give the illusion of danger. His wit and reluctance to harm anyone made him a quirky and somewhat beloved figure.
After years of robbing stagecoaches in California, Black Bart was finally captured in 1883. His capture was a triumph for the authorities, but his strange legacy remains. Though his career was short-lived, Black Bart’s unique blend of charm, poetry, and nonviolence continues to set him apart from the other infamous outlaws of the Old West.
9. Doc Holliday
Doc Holliday wasn’t just a dentist—he was also one of the most feared gunfighters of the Old West. A close friend of Wyatt Earp, Holliday played a key role in the famous O.K. Corral shootout, where his deadly accuracy with a revolver earned him legendary status. Despite suffering from tuberculosis, Doc lived a reckless and dangerous life, often putting himself in harm’s way in defense of his friends. His sharp wit and deadly skills made him both a feared and respected figure in the Wild West.
Doc’s illness made him unpredictable and even more dangerous, as he seemed to care little about his own survival. His time in the West ended prematurely when he died of tuberculosis in 1887, but his legacy as one of the toughest and most loyal figures of the frontier lives on. Holliday’s name is still associated with the true spirit of the Old West—loyalty, danger, and a quick trigger finger.
10. Clay Allison
Clay Allison was a notorious gunslinger known for his unpredictability and erratic behavior. He had a reputation for settling disputes with violence, even going so far as to decapitate a man and display his head as a warning. Allison was known for his wild antics, including dancing naked on tables while firing revolvers into the air. His erratic nature made him just as dangerous to those around him as it did to his enemies.
Despite his chaotic and violent lifestyle, Allison became a legend of the Old West. His career as a gunslinger was filled with high-stakes confrontations, but it was his unpredictability that made him stand out. His reputation for being a loose cannon ensured his place among the most feared figures of the frontier, and his legend remains as wild as his behavior.
11. Sam Bass
Sam Bass was a small-time thief who turned into one of the most feared train robbers in Texas. Bass and his gang were known for their daring heists, including one of the largest train robberies in Texas history, where they made off with $60,000 in gold coins. His ability to outsmart lawmen earned him a reputation as a cunning and elusive outlaw. However, his career came to a bloody end when he was ambushed by Texas Rangers in 1878.
Despite his relatively short criminal career, Bass became a symbol of the Wild West’s lawlessness and the desperate pursuit of wealth. His death marked the end of his gang’s reign of terror, but the stories of his exploits lived on in the myths and legends of the time. His daring heists and eventual downfall ensured his place in the annals of Old West history.
12. Bill Doolin
Bill Doolin was the leader of the Doolin-Dalton Gang, known for their daring bank robberies and train heists across Oklahoma. Doolin was notorious for planning his robberies meticulously and escaping without a trace. However, his criminal career eventually caught up with him, and after a series of bloody shootouts with lawmen, he became one of the most wanted men in the West. His gang was eventually wiped out, and Doolin himself met his end in 1896 when he was killed by a posse.
Doolin’s career as an outlaw has made him a figure of both infamy and fascination. His ability to escape justice for so long and his cunning in planning robberies made him one of the most dangerous men in the Old West. Today, his story is a part of the larger tapestry of frontier lawlessness, a reminder of the harsh and often brutal life that marked the Wild West.
