Famous Outlaws of the Olden Days

If you’ve ever watched a classic Western movie, you’ve probably seen characters based on real-life gunslingers and lawbreakers from the Wild West.

These outlaws often lived fast, dangerous lives – and many of their stories became legends.

Some of them robbed trains and banks, others got into deadly shootouts, and a few even wore a badge at one point.

The truth behind their stories can be hard to pin down, but that’s part of what makes them so fascinating.

Let’s dive into the lives of some of the most famous outlaws of the Old West.

Billy the Kid, born Henry McCarty, also went by aliases like William H. Bonney. He grew up in a rough part of New York and later moved west with his mother.

After her death, he was left to survive on his own as a teenager.

He first got into trouble for stealing food, but things escalated quickly. He joined a gang of cattle rustlers and was later caught up in the Lincoln County War, a violent feud between rival ranchers in New Mexico.

This conflict is where he gained most of his reputation as a gunfighter.

Billy escaped from jail several times, which added to his legend. One of the most famous events was his escape in 1881 from the Lincoln County Courthouse, where he shot two deputies and fled.

His daring actions made him both admired and feared across the region.

Billy the Kid is portrayed in the following films:

• Young Guns (1988)
• Young Guns II (1990)
• The Left Handed Gun (1958)
• Pat Garrett and Billy the Kid (1973)
• Billy the Kid (1941)
• The Kid (2019)

Doc Holliday’s story is full of contradictions. He was a Southern gentleman, trained dentist, and a man who turned to gambling and gunfighting due to poor health.

After being diagnosed with tuberculosis, a deadly disease with no cure at the time, he moved west hoping for relief in the dry air.

He became friends with Wyatt Earp, a well-known lawman, and joined him during the famous Gunfight at the O.K. Corral in 1881. That 30-second shootout in Tombstone, Arizona, involved lawmen facing off against a gang known as the Cowboys.

Despite his frail health, Doc was known to be fearless.

He once said, “I’m your huckleberry,” a line made famous by modern movies. He died in a Colorado hotel at age 36, surrounded by whiskey bottles and playing cards.

Wyatt Earp is portrayed in the following films:

• Tombstone (1993) – Val Kilmer
• Wyatt Earp (1994) – Dennis Quaid
• Gunfight at the O.K. Corral (1957) – Kirk Douglas
• Doc (1971) – Stacy Keach
• Hour of the Gun (1967)

Jesse James wasn’t just a robber - he was also seen as a symbol of rebellion after the Civil War.

He fought as a Confederate guerrilla in Missouri, where brutal warfare blurred the lines between soldier and outlaw.

After the war, Jesse and his brother Frank formed a gang that robbed banks and trains across the Midwest. Many viewed them as folk heroes, especially since their targets were often tied to northern banks or railroads.

However, Jesse’s crimes were brutal. In one instance, he shot a cashier in the head during a failed robbery, claiming it was a case of mistaken identity. His letters to newspapers tried to justify his actions, making him one of America’s first criminals to use media for publicity.

In 1882, Robert Ford—one of his own gang members—shot Jesse in the back while he was dusting a picture on the wall.

Jesse was 34 years old.

Jesse Jame is portrayed in the following films:

• The Assassination of Jesse James by the Coward Robert Ford (2007) – Brad Pitt
• American Outlaws (2001)
• Jesse James (1939)
• The Long Riders (1980)
• The True Story of Jesse James (1957)

John Wesley Hardin was so violent that even other outlaws feared him. Born in Texas in 1853, his first confirmed killing was at age 15.

He claimed that he had to kill to survive in a lawless world, but many of his killings were over petty arguments. During one stretch, Hardin was constantly on the run.

He reportedly killed a man just for snoring too loud in a hotel room. He also fought in gunfights with Texas Rangers, escaped from jail, and even fled to Florida under a fake name.

While in prison, he studied law and hoped to change his life after his release. Unfortunately, he returned to old habits and got into disputes.

In 1895, he was shot in the back of the head by a lawman named John Selman.

John Wesley is portrayed in the following films:

• The Lawless Breed (1953) – Rock Hudson
• Johnny Reno (1966) – features a fictionalized version
• El Dorado (1966) – inspired by his legend, though not directly named

Butch Cassidy was known for his charm, wit, and unusual approach to crime.

Born in Utah, he had a reputation for being nonviolent, often choosing to intimidate rather than shoot. That didn’t stop him from becoming one of the most wanted men in the West.

He led the Wild Bunch, a gang famous for their well-planned train and bank robberies. They once robbed a bank in Idaho and got away with over $30,000. Butch used the money to throw lavish parties and even tried to live a quiet life on a ranch.

Eventually, he and the Sundance Kid fled to South America to escape the law.

They may have continued robbing banks in Bolivia and Argentina, though it’s unclear if they survived the final shootout with Bolivian soldiers in 1908.

Butch Cassidy is portrayed in the following films:

• Butch Cassidy and the Sundance Kid (1969) – Paul Newman
• American Outlaws (2001) – features both Cassidy and the Sundance Kid
• Blackthorn (2011) – imagines an older Butch Cassidy surviving in Bolivia

The Sundance Kid, Henry Longabaugh, was quieter and more serious than Butch Cassidy.

He joined the Wild Bunch in the 1890s and became known for planning robberies that involved precise timing and fast getaways.

He was a skilled marksman and rode expert horses. Like Cassidy, he preferred to avoid unnecessary violence. The two had such a strong bond that they moved to South America together with Etta Place, Sundance’s partner.

The trio lived for a time in Argentina, pretending to be ranchers.

They were eventually tracked by lawmen and forced into hiding. It’s believed that Sundance was killed alongside Butch Cassidy in Bolivia, though some legends claim he returned to the U.S. and lived under a different name.

The Sundance Kid is portrayed in the following films:

• Butch Cassidy and the Sundance Kid (1969) – Robert Redford
• American Outlaws (2001)
• Blackthorn (2011)

Miller was a walking contradiction—a devout churchgoer who also worked as a professional killer. He always wore a black frock coat and carried a double-barreled shotgun.

His calm demeanor made his actions even more chilling.

Miller is most infamous for murdering Pat Garrett, the man who killed Billy the Kid. Some historians believe he was hired to do it, continuing his streak of being a "hitman" of the Old West.

His downfall came when he killed a former Deputy U.S. Marshal in Oklahoma. Townspeople were so angry that they dragged Miller and his partners from jail and lynched them.

His last words? "Let 'er rip."

James Miller is portrayed in the following films:

While not featured in many major films, Miller appears or is referenced in the following

• Deadly Shooters (2001, TV docudrama)
• The Gunslingers (2014, American Heroes Channel docu-series)

Note: Miller is less often depicted in fiction, but he features in several Western documentaries and historical series.

Sam Bass started out as an honest man, working as a cowhand and stagecoach driver. But when he and a partner decided to keep the profits from a cattle drive, he crossed the line into outlaw territory.

He became a leader of a small gang that specialized in robbing trains.

Their biggest hit was the Union Pacific gold train robbery in 1877, which brought in $60,000—a massive fortune for the time.

Bass enjoyed gambling and horse racing with his new wealth. But law enforcement was never far behind.

After being betrayed by an informant, Bass was shot in Round Rock, Texas, and died two days later—on his 27th birthday.

Sam Bas is portrayed in the following films:

• Badman's Country (1958)
• The Texas Rangers (1951)
• Calamity Jane and Sam Bass (1949)
• American Outlaws (2001, loosely based)

Dallas Stoudenmire was a former Confederate soldier who became a respected lawman.

He was hired as marshal of El Paso in 1881, when the city was known as one of the most dangerous places in the West.

Within days of taking the job, he took part in the infamous "Four Dead in Five Seconds" gunfight, where he killed three men in a matter of moments. His fast draw and dual revolvers made him feared and admired.

However, he made many enemies and became caught in local feuds. One of these disputes led to a deadly shootout in 1882, when he was ambushed by the Manning brothers.

Stoudenmire was killed, but his short time in El Paso had a lasting impact.

Dallas Stoudenmire is portrayed in the following films:

Rarely portrayed in mainstream Westerns, but appears in the following - 

• The Gunfighters (1987, TV movie)
• El Paso (1949, loosely inspired by his story)
• Legends & Lies: The Real West (TV series, 2015)

John King Fisher had a flair for fashion and violence.

He often wore flashy clothes and gold jewelry, making him easy to spot. Despite his style, he was ruthless and feared in southern Texas.

He led a gang that raided Mexican settlements, leading to cross-border conflicts. His most famous feat was taking on four attackers by himself, killing all of them.

Later in life, Fisher tried to go straight. He even served as a sheriff for a time and settled into ranching. But in 1884, he was ambushed and killed in San Antonio, along with former lawman Ben Thompson.

The murder was likely payback for past killings.

King Fisher is portrayed in the following films:

King Fisher is a lesser-known figure in film, but appears in the following - 

• The Texas Rangers (1951)
• The Gunfighters (1987, TV movie)
• Featured in episodes of The Gunslingers (2014)

Life in the Old West was unpredictable – often violent, and almost always short-lived for those who walked on the wrong side of the law.

Whether they were ruthless bandits, reluctant criminals, or lawmen-turned-gunslingers, these figures lived fast and dangerously, carving out names that would echo through history.

While many of their stories have been stretched or softened over time, their larger-than-life reputations still capture our imagination.

We might not want to run into any of them in a dark saloon, but exploring their legends (Truth or Myth) is a thrilling way to revisit one of America’s most lawless eras.

Did we miss someone you think should’ve been on the list? Which outlaw’s story surprised you the most?

Let us know in the comments!