10 cowboys who became legends and 10 outlaws who became nightmares

Goodnight helped create the Goodnight-Loving Trail, driving cattle northward with a discipline that impressed even his rivals. His reputation was established because he combined the toughness of the frontier with a builder’s spirit, transforming a perilous route into a passable road.

Nat Love, who published an autobiography toward the end of his life, described a career that spanned from cattle driving to rodeo competitions across several territories. His legacy is significant because it preserves the reality that Black cowboys played a central role in the cattle industry—and were not merely a footnote.

Pickett became famous for bulldogging, a rodeo technique that involves pinning a steer to the ground, and his talent transformed a farm task into a spectacle. His fame spread through Wild West shows and early films, cementing the image of the hardworking cowboy in popular culture.

Ikard worked for Charles Goodnight and earned a reputation for endurance on long drives, when endurance was synonymous with survival. Goodnight’s tribute, engraved on Ikard’s headstone, helped ensure that his name would not be forgotten, as has happened to so many other cowboys.

Hickok worked as a scout and a lawman and was a product of the same frontier economy that produced cowboys. He became legendary because his appearance and reputation as a quick-draw gunfighter matched the tales in pulp novels, even if the details were exaggerated.

Cody rode, explored, and hunted, then turned those experiences into a traveling show that brought the West to audiences around the world. He became a legend by controlling the narrative, transforming his pioneering skills into a spectacle that audiences could buy into.

Mulhall made a name for herself as one of the first cowgirls, performing in Wild West shows where she demonstrated her lassoing and horseback riding skills at a time when women were expected to remain mere decorative figures. Her legacy lives on because she proved that the saddle and the spotlight weren’t just for men.

Threepersons was a cowboy who later became a lawman, known for his tracking skills and his composure under pressure. His name lives on in the Threepersons holster style, designed for quick and safe draw.

Rogers started out as a cowboy and farmhand, then turned his cowboy skills into vaudeville charm and sharp wit. His legend stems from the fact that he was able to present the voice of cowboys—witty, generous, and undeniably American—on the national stage.

Bascom helped modernize rodeo events and equipment, shaping the sport as it transitioned from ranch competitions to organized arenas. His legacy shows how cowboy culture has continued to evolve rather than becoming frozen in a single postcard image.

This same landscape has also produced people who made a career out of intimidation, theft, and bloodshed, and their stories travel just as far and endure for generations. Here are ten outlaws who have captivated our collective imagination.

James became infamous after the Civil War for robberies that were brutal in their execution and carefully mythologized in the newspapers. His admirers portrayed him as a folk hero, but the archives show that he was a violent criminal whose fame was built on politics and publicity.

Billy the Kid, born Henry McCarty, rose to fame during the Lincoln County War in New Mexico and died young after a life of shootouts and on the run. His nightmarish reputation stems from how quickly murder became his identity—and then a form of entertainment.

Hardin claimed to have killed dozens of men, and while the number is disputed, his string of shootings is not. He became a nightmare because he treated lethal force as routine and then tried to portray it as mere expertise.

Cassidy’s gang carried out daring robberies on trains and in banks, and his charm softened their image in later accounts. The nightmare is that these crimes were carried out through threats and the use of firearms, and that the romanticized version overlooks the employees and passengers who had their eyes fixed on the gun barrels.

Harry Longabaugh, who was associated with the Wild Bunch, built a reputation as a consistent gunman at a time when consistency could mean effective violence. His story shows how crime could become a traveling business, crossing borders when the pressure mounted.

Bass went from working with cattle to a life of crime, and his short career was marked by train robberies that prompted Texas law enforcement to hunt him down relentlessly. His legend lives on in ballads, but an armed robbery is first and foremost a source of terror, and only then does it become music.

Black Bart, a stagecoach robber in California, became known for his polite notes and theatrical style. The nightmare was that this politeness was merely a disguise, behind which lay armed robberies targeting travelers and the road’s meager safety net.

Starr moved in the underworld circles of Indian Territory and rose to fame through a mix of connections, accusations, and image. Her nightmarish notoriety illustrates how a public hungry for scandal can turn a life on the fringes of crime into a brand—and how that brand attracts dangerous companions.

The Dalton Gang attempted to rob two banks at once in Coffeyville, Kansas, but the attempt ended in a violent street battle. They became a nightmare because their ambition increased the risk for everyone nearby, and ordinary citizens found themselves caught in the crossfire.

Horn worked as a scout and interpreter, then as a mercenary in territorial wars where money solved all problems. His nightmarish nature stems from the cold logic of contract killing—a form of violence that seems modern even in an old photograph.