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10 Famous Cowboys & Outlaws Who Ruled the Wild West

10 Famous Cowboys & Outlaws Who Ruled the Wild West

The original cowboys & outlaws of the Wild West are some of the most fantastic historical figures in American History.

Tough cowboys, strong and smart enough to thrive, always ready with a gun on their hip at all times, soon became the natural leaders in the Old West. 

The stories of these famous cowboys, some champions and some villainous scum, shaped the legends of the Wild West…never to be forgotten. 

Here are the 10 most famous cowboys, outlaws, & gunslingers of the Wild West:

Henry McCarty “Billy the Kid” (1859 – 1881) 

Henry McCarty “Billy the Kid", Wild West outlaw posing for the camera

Probably the most famous outlaw of the Wild West is Billy the kid. Infamous for being a deadly gunfighter, Billy the Kid bested and killed eight men before the age of 21. 

An orphan at age 15, arrested the first time at 16, he fled to Arizona as an outlawed fugitive.

After the murder of a blacksmith in Arizona, Billy the Kid returned to New Mexico to join a band of cattle rustlers who called themselves “The Regulators”. 

News stories across the country publicized Billy the Kid and his murderous spree. 

Sheriff Pat Garrett captured the Kid approximately one month after the New York Sun spotlighted his crimes. After trial, conviction, and a jailbreak before his hanging, the Kid was on the run again. 

Garrett, however, was relentless in his track of the outlaw. Sheriff Garrett shot and killed Billy the Kid at Fort Sumner, at age 21, on July 14, 1881. 

Pat Garrett (1850 – 1908) 

Pat Garrett, Wild West lawmaker who killed Billy the Kid

Pat Garrett was a bartender, a customs agent, and most notably a tenacious American Old West lawman. Raised on a plantation in Louisiana, Garrett’s family lost everything in the American Civil War. 

When Garrett killed his first man, a fellow Buffalo Hunter, he promptly turned himself in. The authorities declined to prosecute. 

He then migrated to New Mexico, where he met his wife and settled into the life of a frontier cowboy and rancher. 

Garrett was elected the Sheriff of Lincoln County, New Mexico. Shortly after, his encounters and tracking of notorious Wild West Outlaw Billy The Kid would begin. 

After several misses, that resulted in the capture of other wanted outlaws, Pat Garrett tracked the Kid down at Fort Sumner in 1880 and took him to trial. 

After Billy the Kid escaped jail, Pat Garrett resumed his track of the outlaw. Garrett concealed himself in the shadows of his quarry’s location.  

When Billy the Kid entered the room he asked twice, “¿Quién es?” (“Who is it?”) and the response from Garret was to shoot the outlaw two times in the chest. 

Robert Leroy Parker “Butch Cassidy” (1866 – 1908)

Butch Cassidy, infamous cowboy and outlawing posing for the camera

Famous American train and bank robber, Butch Cassidy was the leader of the “Wild Bunch Gang”.

Growing up as a cowboy in Colorado, Butch Cassidy walked the line of work with the ranchers and theft of their stock. 

He robbed his first bank in Telluride, Colorado in 1889. He fled with his band to Robbers Roost, a remote hideout in southeastern Utah. Traveling to and from hideouts across four states, the outlaw was regularly on the move. 

The Wild Bunch was ultimately formed with seven other outlaws and gunslingers. One notable WIld Bunch member was Cassidy’s wife, cowgirl outlaw Laura Bullion

The Wild Bunch was responsible for bank robbery, ambushes of gold mine couriers, train robberies, and many shootouts with the law.

At one point, Cassidy attempted to strike an arrangement for amnesty with the Governor of Wyoming but spoiled the deal by robbing a Union Pacific train. 

Following multiple lucrative train robberies, Cassidy and his gang became the focus of the Pinkerton men. Several of the gang were shot and killed in the pursuit. 

Butch Cassidy fled to South America in an attempt to escape the law. After a holdup in Bolivia, local authorities surrounded the house to attempt to capture Cassidy and his partner. 

A shootout left Butch Cassidy and his partner dead. Found in the hideout, shot multiple times in the arms and legs, each man had a bullet hole to the head. 

It is believed that Cassidy, in an attempt to put them out of their misery, shot his partner in the forehead before turning the gun to himself with a shot to the temple. 

Jesse James (1847 – 1882)

Jesse James, an infamous outlaw of the Wild West

Jesse James was a brutal American outlaw, bank and train robber, guerilla, and leader of the “James-Younger Gang”. James started as an outlaw with a group of pro-Confederate guerillas known as “The Bushwackers”. 

Throughout the American Civil War, James and the Bushwackers traveled throughout Missouri and Kansas in a violent and bloody crime spree.  

After the war, the James-Younger Gang was formed. Trains, Banks, and stagecoaches were all targets of their brutally murderous plans. 

The spree of 1866 and the decade that followed was an incredible record of theft and bloodshed. Following an attempted robbery of a bank in 1876, several of the gang members were killed. 

Lawmen on the hunt posted a high reward for the capture of Jesse James, dead or alive. A new recruit to the gang, eager to claim the bounty, shot and killed Jesse James on April 3, 1882. 

James Butler “Wild Bill” Hickok (1837 – 1876)

James Butler “Wild Bill” Hickok portrait

Wild Bill Hickok is a popular folk hero of the Old West. Wild Bill started his adventures as a stagecoach driver and lawman in Nebraska and Kansas. 

His service as a Union soldier in the American Civil War gained him publicity as a scout. 

It was during the war that Hickock first met William “Buffalo Bill” Cody”. The pair would go on to share the tales of the Wild West with the rest of the world.

After the war, he turned to acting, marksman shooting, and professional gambling. He was involved in several notable shootouts. 

Hickok spent some time with Buffalo Bill Cody in his Wild West Show but was never very happy with his acting roles there. 

He continued with the show for a short time before returning to the comfort of the gambling tables. 

In 1876, while playing poker in a Deadwood, Dakota Territory saloon, Wild Bill was shot and killed by another gambler Jack McCall. The hand of cards Wild Bill Hickok was dealt at the time of his death, two pairs; black aces and eights were dubbed “The Dead Man’s Hand”. 

William Frederick “Buffalo Bill” Cody (1846 – 1917)

William Frederick “Buffalo Bill” Cody

An American soldier, bison hunter, and showman, Buffalo Bill Cody was the founder of Buffalo Bill’s Wild West Show. Beginning on the frontier, Bill was a Pony Express Rider. He fought as a Union soldier in the American Civil War. 

During the Indian Wars, Buffalo Bill received a Medal of Honor from the US Army while serving as a civilian scout. 

Cody’s legend grew, and he established the wildly popular re-enactment show Buffalo Bill’s Wild West. Recruiting other legends, including Wild Bill Hickok, Texas Jack, Calamity Jane, Sitting Bull, and Annie Oakley, Wild Bill’s show grew to international acclaim. 

Acts such as trick-shooting, staged races, sideshows, and full re-enactments entertained audiences all over the world. Crowds could watch Pony Express riders racing through the plains amid wagon trains and Indian attacks. 

Stagecoach robberies and gunfights delighted the onlookers, before culminating in the final scene of Custer’s Last Stand. 

John Henry “Doc” Holliday (1851 – 1887)

John Henry “Doc” Holliday

Best known for his role with Wyatt Earp and the Gunfight at the O.K. Corral, Doc Holliday was a scoundrel of a Wild West Cowboy. 

Holliday was an educated man with a degree in dentistry, hence the nickname, who contracted tuberculosis in his early twenties. He moved out West in search of an arid climate to alleviate the symptoms of his disease. 

Doc was involved in several violent confrontations, and quickly developed a reputation for instigating, and winning gunfights. His skill with a fast gun came in handy for Wyatt Earp on a fateful day in Dodge City. 

Doc Holliday’s fortuitous interference in a saloon standoff likely saved Wyatt Earp’s life. 

Bartholemew “Bat” Masterson (1853 – 1921)

Bartholemew “Bat” Masterson

Bat Masterson distinguished himself on the Western frontier as a gunslinger and buffalo hunter who found himself Sheriff of Dodge City, Kansas. 

As Sheriff, Masterson was involved in several notable shootouts. One of them ending badly with his brother being shot and killed in the line of duty at Bat Masterson’s side. 

Sheriff Masterson captured notorious train robbers, and murderers before getting involved in the Royal Gorge Railroad War. 

Despite having no authority in that state, Bat Masterson recruited gunslinging cowboys, to possibly include Doc Holliday, and joined the fight. Bat Masterson moved on and joined Wyatt Earp in Tombstone, but didn’t stay long. 

His attempt to return to Dodge City failed thanks to a gunfight at the local saloon. The scene was so chaotic, supportive-bystanders joined in the shooting on both sides. 

After fighting through the west as a lawman for years, occasionally at Wyatt Earp’s side, Bat Masterson made full-time journalism his profession. 

As a journalistic writer, Bat shared his first-hand knowledge with New York and the world. 

Published after the turn of the century, he wrote several biographies of the wild west era and the famous gunfighting cowboys. 

Wyatt Earp (1848 – 1929)

Wyatt-Earp, famous cowboy and outlaw of the Wild West

The central figure of the Old West legend of the Shootout at the O.K. Corral, Wyatt Earp was a lawman and a gambler in Arizona. 

It was there that Earp earned his reputation as a strong lawman in Kansas, but he soon relocated to Dodge City. 

It was in Dodge City that Wyatt befriended several of his future allies, including Doc Holliday. His next town, Tombstone, was the location and origin of Wyatt’s legacy. 

A five-month vicious and deadly conflict raged between outlaws known as The Cowboys Gang and the Earp brothers.  

Mid-afternoon on October 26, 1881, five members of the Cowboy gang, who had been threatening to kill the remaining Earps for weeks, were loitering around the O.K. Corral. 

Wyatt, Virgil and Morgan Earp, with Doc Holliday stood paces from The Cowboys and a gun fight broke out.  

The blistering thirty-second fight ended with three Cowboys dead, and Morgan, Virgil, and Holliday shot but still standing. 

One of the Cowboys filed murder charges against the Earp men, but there was not enough evidence for a conviction. The Cowboys bent on revenge, ambushed Virgil Earp, and assassinated Morgan Earp.  

Convinced the law was unreliable, Wyatt Earp took matters into his own hands. Wyatt Earp formed a posse and hunted down and killed the remainder of the Cowboy gang. 

In all of the gunfights, Wyatt Earp was never wounded. 

John “The Duke” Wayne (1907 – 1979)

Wild West movie actor, John Wayne

John Wayne was not a real Wild West Cowboy, but his portrayal of the era is what earns him a special place on this list. 

Wayne’s unforgettable image is what many of us picture today as what an Old West Cowboy looks, sounds, and acts like. 

His leading role in America’s Western Hollywood films brought to life the nation’s frontier heritage. The Duke took on every facet of the Wild West. 

We could watch him protect the homestead, fight with crooked gunslingers, work with or against the Native Americans, fight as a frontier soldier, or ride a hard cattle drive. 

Surrounded by casts of characters inspired by the men on this list, John Wayne was the idyllic Old West Cowboy. 

Renowned for being as true to that portrait off-screen as well, it only seems right to include him on this list. Especially as, in reality, he was one of the best cowboys America has ever known.

Also read, top 10 famous cowgirls & female outlaws of the Wild West.