1. Billy the Kid
Billy the Kid, born Henry McCarty, is often remembered as one of the most notorious outlaws of the Old West. According to Britannica, his story gained widespread attention due to his youthful defiance and the numerous legends surrounding his life. It’s said that Billy killed his first man at just 15, and he quickly became a skilled gunslinger. His notorious escape from jail in 1881, during which he killed two deputies, cemented his place in American folklore.
His outlaw career, filled with cattle rustling and robberies, made him both feared and admired. Despite the fact that his actual kill count was likely much lower than the 21 often attributed to him, his legend only grew over time. His death, at the hands of Sheriff Pat Garrett, remains one of the most mysterious parts of his tale. Some speculate that Billy faked his own death, adding another layer of myth to his already legendary life.
2. Jesse James
Jesse James became a symbol of resistance after the Civil War, using his skills as a former Confederate soldier to wage a personal war against the Union. His robberies targeted banks, trains, and stagecoaches, and his meticulous planning made him notorious across the Midwest, PBS explains. He wasn’t just a ruthless outlaw—his efforts to share stolen goods with the poor earned him a “Robin Hood” reputation. His gang, known for its daring heists, struck fear into the hearts of lawmen and ordinary citizens alike.
In 1882, Jesse’s life ended tragically when a member of his own gang, Robert Ford, shot him in the back for the reward money. Though his death seemed like an end to his outlaw career, it only added to the mystery surrounding him. Over time, books, movies, and songs turned him into a tragic figure, symbolizing the struggle of the defeated South. His rebellion against the federal government and his violent end left him with a place in the American imagination that still thrives today.
3. Belle Starr
Belle Starr, often referred to as the “Bandit Queen,” shattered the mold of women in the Old West. Born into a relatively wealthy family, she chose a life of crime, becoming involved with infamous gangs, Humanities Texas explains. Belle was known for her beauty, charm, and intelligence, and she ran successful cattle rustling and horse theft operations. Her ability to evade the law for years made her an enigmatic figure, and she became a symbol of independence in a male-dominated world.
Though she lived a daring life, it all came to a violent end in 1889 when she was ambushed and shot while riding home. The exact circumstances of her death remain a mystery—some believe it was due to personal vendettas, while others think it was a consequence of her criminal life catching up with her. Regardless of how she died, Belle’s legacy has endured as one of the most iconic female outlaws of the Old West. She remains a symbol of courage and defiance in the face of danger.
4. Butch Cassidy
Butch Cassidy, the leader of the infamous Wild Bunch gang, was not just a criminal; he was a mastermind of heists and escape, Britannica explains. Alongside his partner, the Sundance Kid, Butch orchestrated some of the most daring robberies across the American West. He was known for his charm, strategic mind, and ability to avoid unnecessary violence, making him a unique figure in the world of outlaws. His carefully planned heists often had him outsmarting lawmen and escaping into hiding with remarkable precision.
The mystery surrounding Butch’s later years only added to his legend. After fleeing to South America to escape capture, Butch’s ultimate fate remains unclear. Some believe he was killed in a shootout, while others claim he and the Sundance Kid lived their final years in obscurity. Regardless of the truth, Butch Cassidy’s story is a testament to the allure of the ultimate escape, and his status as one of the most legendary outlaws endures.
5. The Sundance Kid
Harry Longabaugh, better known as the Sundance Kid, was the quieter but equally deadly partner of Butch Cassidy. Though he didn’t seek the limelight as Butch did, Sundance was a skilled sharpshooter whose accuracy and calm under pressure made him feared across the West, according to Linda Wommack from Cowboy State Daily. His abilities were key to the Wild Bunch’s success, and he quickly gained a reputation as one of the best gunslingers of the time. Despite his violent profession, Sundance was known to prefer a life of minimal bloodshed, focusing more on the heist than the violence.
Much like his partner Butch, the mystery surrounding Sundance’s death only added to his mystique. Did he die in a final shootout with lawmen in Bolivia, or did he manage to vanish into obscurity? Without definitive evidence, his fate became part of the myth surrounding the Wild Bunch’s final days. Today, his partnership with Butch Cassidy makes him an enduring figure in the pantheon of Old West outlaws.
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.
