The Wild West wasn’t just dusty streets and cowboy duels. It was ruled by savage, unpredictable men. Today, we’re counting down from the dangerous to the ones so ruthless their names still echo through legend. Stick around for number one. You won’t believe how it really ended. Number 10, Klay Allison. Klay Allison was the very definition of a wild man.
A notorious gunfighter infamous for his extreme violence. In 1870, for example, Allison led an enraged mob to the local jail to free a man named Charles Kennedy, recently convicted of murder. But Allison didn’t break him out to spare him. Instead, he personally lynched Kennedy. And for Allison, that still wasn’t enough. He went on to decapitate the man and mount his head on a steak, proudly displaying it at the local saloon.
Needless to say, this horrified the children who wandered in for a drink. Allison’s wild streak didn’t stop there. He was known to ride through town completely naked, save for the pistol on his hip. One of the most infamous tales, however, involves a dinner invitation from Chunk Colbert, another feared gunfighter rumored to have killed seven men.
It was widely known that Colbert wanted Allison dead, and Allison knew it, too. Still, he accepted the dinner invite. Midmeal, Colbert suddenly leapt from his chair, drawing his pistol in an attempt to kill Allison, but his gun struck the edge of the table, stopping him from aiming any higher.
In a single fluid move, Allison pulled his own revolver and shot Colbert square between the eyes. When asked why he’d din with a man he knew intended to kill him, Allison simply replied, “Because I didn’t want to send a man to hell on an empty stomach.” We’ve got some insane stories ahead, so if you’re into Wild West history, you might want to hit subscribe so you don’t miss the next one. Number nine, Cherokee Bill.
Crawford Goldsby, better known as Cherokee Bill, was a feared outlaw, credited with killing anywhere from 8 to 13 men. His life of crime began in 1894 at just 18 years old when he confronted a man who had beaten up his brother. Once face to face, Bill apparently decided he didn’t want to risk taking a beating himself.
He shot the man instead. From that moment on, he spent the rest of his life as a fugitive. Not long after, Cherokee Bill joined an outlaw crew known as the Cook Gang, a group notorious for robbing banks, trains, and stage coaches. Bill’s criminal record grew quickly and was filled with brutal acts. To get a sense of his relentless pace, let’s look at just a short stretch of his activity.
On June 17th, 1894, he shot and killed Deputy Sheriff Sequoia Houston during a gunfight. Only a month later, on July 4th, Bill celebrated the holiday by gunning down two men. Two days after that, on July 6th, he was rumored to have killed a railroad worker. By July 30th, Bill and the Cook gang were robbing the Lincoln County Bank in Oklahoma territory.
His violent spree never slowed down, and it continued until his capture on January 31st, 1895. Even behind bars, Bill wasn’t finished. Somehow managing to get his hands on a revolver, he attempted to escape, shooting a jail guard in the stomach and back. But the plan failed, and he was quickly locked back in his cell. On March 17th, 1896, Cherokee Bill, one of the most infamous outlaws of the era, was hanged for his crimes.
When asked for any last words, he simply said, “I came here to die, not make a speech.” Which, let’s be honest, sounds less like stoic bravery and more like a man who just hated public speaking. Number eight, George Parrot. Most outlaws of the Wild West had some seriously intimidating nicknames. names like Billy the Butcher, Shotgun John Collins, Pistol Pete, Wild Bill Hickok, Texas Jack, Bronco Bill, and even the Kentucky Cannibal, though that last one’s still up for debate.
The point is, these names were cool, menacing, and memorable. Unfortunately for George Parrot, he drew the short straw in the nickname department. He became known as Big-Nosed George or sometimes Big Beak Parrot, easily one of the least flattering monikers in outlaw history. And with a nickname like that, it’s not surprising the man carried a chip on his shoulder, channeling his anger into some of the most grotesque crimes imaginable.
From robbing trains, stage coaches, and cattle to outright cold-blooded murder. After years of lawlessness, his downfall began in August of 1878 when big-nose George and his gang tried to derail a train in Wyoming by removing a stake from the tracks. But their plan was foiled when a railroad worker spotted them.
Realizing they’d been identified, the gang fled to Rattlesnake Canyon. Unaware they were being tailed by two law men trained in tracking. Following the faint hoof prints of the gang’s horses, the law men caught up to them, but were spotted and murdered on the spot. These killings earned George a hefty bounty of $20,000, the equivalent of over $600,000 today.
Still, it wasn’t until 1880 that he was finally captured. While in jail, George managed to get hold of a pocketk knife, sawing through his shackles before smashing the jailer over the head, fracturing his skull. But his escape came to a screeching halt when the jailer’s furious wife held him at gunpoint.
And she was likely even more disgusted at the sight of her now misshapen, battered husband. Word of the escape attempt spread quickly, drawing a crowd of 200 people. But this wasn’t a rescue party. It was an angry mob. They dragged George from his cell, slipped a rope around his neck, and lynched him on the spot.
In the aftermath, his skull was turned into an ashtray and his skin was fashioned into a pair of shoes, both of which are still on display in museums today. Number seven, Bill Dulan. Bill Dulan was a notorious outlaw and the founder of the Wild Bunch Gang, a group responsible for a string of crimes ranging from robberies to coldblooded murder.
His reign of lawlessness spanned from 1892 to 1896, mostly across Oklahoma and Indian territory. It didn’t take long for the Wild Bunch to rise to the top, becoming one of the richest and most feared gangs in the West. They amassed an estimated fortune of $165,000, worth over $5 million today. Depending on when you’re watching this, that’s either enough for a luxurious single family home or used pickup truck if prices keep going the way they are.
Their success at robbing trains and banks was so great that states had little choice but to put large bounties on each member’s head. They were wanted dead or alive. And by 1895, most of them had been taken out by law men or bounty hunters, eager for the reward. Bill himself was captured on January 15th, 1896 and thrown in jail.

But just 6 months into his sentence, he managed to get his hands on a revolver holding a jail guard at gunpoint and forcing him to unlock the door. His escape triggered a massive manhunt, which ended with Dulan cornered inside a farmhouse surrounded by lawmen. In order to surrender peacefully, he instead walked out guns blazing, only to be dropped instantly by a shotgun blast.
Turns out taking on 20 armed men alone is never a winning strategy. Number six, Jim Miller. James Brown Miller, better known as Killing Jim or Killer Miller, was an outlaw, a professional hitman, and at one point even a law man. Widely regarded as one of, if not the most violent men of the Wild West, Miller is estimated to have killed at least 12 people.
Some reports claimed the number was closer to 50, though those reports came from Miller himself, which, let’s be honest, was some clever self-promotion. Early in his career as a lawman, some of his killings could be considered justified, targeting criminals. But once he switched sides and became a hired gun, most of his victims were just unlucky targets of cold-blooded murder.
He charged $150 per job, roughly $5,000 in today’s money, and spent years taking contracts to eliminate men across the West. In 1908, three wealthy men hired Miller to kill former deputy US Marshal Alan Augustus. The deal was straightforward. Pay Miller $1,700, and once Augustus was gone, they’d claim his land. The very next day, Miller ambushed him on his property, blasting him twice with a shotgun.
As Augustus lay dying, his wife rushed to his side, and with his last bit of strength, he managed to utter the name Jim Miller. It wasn’t long before Miller and the three conspirators were arrested. But word spread quickly that there wasn’t enough evidence for a conviction. That’s when the town’s folk decided to handle things themselves.
A mob broke the four men out of jail, dragged them to a nearby barn and placed each on a platform with a noose around their neck. While the other three pleaded for their lives, Miller stayed calm, showing no fear. Impatient for the inevitable, he shouted, “Let it rip.” and stepped off the platform himself. The mob handled the rest, ensuring none of them left that barn alive.
Number five, Samb Bass. Samb Bass was a notorious train robber and a leader of the Sambass gang, a crew that cemented its place in history by pulling off the largest train robbery in America. But before he became an outlaw legend, Bass actually tried living an honest life. He worked a variety of jobs. Cattle wrangler, horse racer, and allegedly advertising signed spinner.
Okay, maybe not that last one. He even worked for the railroads, loading goods onto freight cars. But Bass’s downfall came from a gambling habit that left him buried in debts he couldn’t pay. That was the turning point. He began robbing stage coaches, but soon realized trains were far more lucrative. Using his insider knowledge from working with the railroads, Bass successfully carried out four straight train robberies just outside Dallas, Texas.
But his biggest score came in 1878 when he and his gang hit a Union Pacific train and made off with $60,000 in gold, worth nearly $2 million today. Following the heist, the gang split up, but Bass didn’t stay retired for long. Later that same year, he formed a new crew and set his sights on a bank in Round Rock, Texas. Unfortunately for him, one of his own men was an outlaw turned informant.
When they arrived at the bank, law men were waiting and a gunfight erupted. Several of Bass’s men were killed on the spot. Wounded, Bass managed to escape on horseback, but was found the next day lying in a pasture north of town, bleeding heavily from a gunshot wound. He was brought back to town where he died the following day.
And trust me, if you think this is bad, wait until you hear what outlaw number one pulled off. While you’re here, a quick like helps me dig up more of these insane stories. Number four, John Wesley Harden. John Wesley Harden might just have been the most cold-blooded killer the Wild West ever saw. His first crime came as a child when after a schoolyard fight, he stabbed a classmate.
By 1868, at just 15 years old, he escalated to murder. During an argument with a man, rather than risk being proven wrong, he ended the discussion by shooting him dead. When Union soldiers came to arrest him for the killing, Harden went on the offensive, gunning down all three. In 1871, while traveling up the Chisum Trail, he killed seven more people, followed by three in Abalene, Kansas.

Over the next few years, he added another four men to his tally. By 1878, Harden had claimed at least 20 lives, though some reports suggest the number could have been closer to 40. His eventual capture came after he murdered both a former state policeman and a sheriff. Convicted, Harden spent the next 14 years in a Texas prison before finally being released.
In 1895, in El Paso, Texas, his girlfriend was arrested for carrying a pistol. Enraged, Harden threatened to kill the arresting officer. Just hours later, Harden was in a local saloon shooting dice when someone walked up behind him and shot him in the back of the head, killing him instantly. The gunman, the very same officer he had threatened earlier that day.
Not willing to risk becoming another name on Harden’s kill list, the officer decided to strike first. When the case went to trial, an El Paso jury acquitted him, deciding he had done the town a public service. Number three, Jesse James. Jesse James is perhaps the most legendary outlaw of the Wild West. His taste for violence started early at just 16 years old when he joined a gorilla group called the Bushwhackers.
Despite the name, they weren’t a bunch of harmless pranksters. They were a proconfederate guerrilla warfare unit during the Civil War, responsible for some of the worst atrocities committed against Union soldiers and their supporters. Two examples stand out. The Lawrence Massacre of 1863 in Kansas, where 150 unarmed men and boys were slaughtered, and the Centriia Massacre of 1864 in Missouri, where 24 unarmed soldiers were executed.
A young Jesse James participated in both. After the war, Jesse, his brother Frank, and several former Confederate gerillas formed the James Younger Gang, soon to become the most feared outlaw crew in American history. They started with banks, then moved on to trains and stage coaches. What made them so feared was simple. They never hesitated to kill.
The bank guard, the teller, the random man walking in during a robbery, no one was safe. They even became the stuff of local folklore, treated like folk heroes for their ties to the Confederate cause. Newspapers sensationalized their exploits. And in some towns, people would gather just to watch their robberies unfold.
From 1869 to 1879, the James Younger gang robbed over 20 banks and countless trains. But after a decade of violence, the gang began to fall apart as more members were killed in shootouts. By 1879, only Jesse and Frank remained, and the bounty on Jesse’s head had grown enormous. Trusting only the Ford brothers, former gang members, Jesse invited them to live with him.
They agreed. But on the morning of April 3rd, 1882, while Jesse was hanging a picture on the wall, one of the brothers shot him in the back of the head. The Fords claimed the reward money soon after and were later pardoned for the killing. Number two, Billy the Kid. Henry McCarti, better known as Billy the Kid, was a notorious outlaw and deadly gunfighter.
His life took a sharp turn in 1874 when, at just 15 years old, his mother died of tuberculosis. His stepfather, unwilling to raise Billy and his brother alone, abandoned them both, leaving the boys as orphans, forced to steal food just to survive. Eventually, Billy was caught for theft and thrown in a local jail.
But one night, he managed to shimmy up the chimney of his cell and escape, marking the start of a life permanently on the run. Over the next few years, he bounced between gangs, committing crimes ranging from robbery to murder, and was arrested several times. By the late 1870s, however, Billy took on an honest job as a cowboy for John Tunl, a businessman with plenty of enemies.
In 1878, those enemies, with help from the local sheriff, sent a group of men to seize Tonsl’s cattle. When Tonsl confronted them, he was shot in the chest and knocked off his horse, then executed with a bullet to the back of the head. This killing sparked the Lincoln County War. A group called the Regulators formed, swearing to take down every man involved in Tonsl’s murder, and Billy was one of them.
They quickly began their revenge. First killing the two gunmen, then ambushing the sheriff and his deputies, wiping them out in a bloody shootout. The war raged for about a year before ending, but Billy was left a wanted man for the sheriff’s murder. In 1880, he was finally captured, tried, and sentenced to hang, but Billy had no intention of going quietly.
On April 28th, 1881, he fought with one of the jail guards, killed him, and took his revolver. From the second floor, Billy taunted the other guard, calling, “Look up, old boy, and see what you get.” When the guard looked up, Billy blasted him with a shotgun taken from the office. Once again, Billy had escaped.
A $500 bounty was put on his head. Dead or alive, and lawmen and bounty hunters began the chase. His luck ran out on July 14th, 1881 when Sheriff Pat Garrett shot him in the chest, ending his life at just 21 years old. It’s believed Billy killed around 21 men during his short, violent life, one for each year he lived.
Number one, Butch Cassidy and the Sundance Kid. Robert Leroy Parker and Harry Longaba are two of the most legendary names in Wild West history. Though most people know them better as Butch Cassidy and the Sundance Kid. They share the top spot because they became partners. But before we get into their rise to outlaw fame, let’s start with Butch Cassid’s beginnings.
Butch would go on to lead and found the Wild Bunch gang, a name inspired by Bill Dulan’s gang, which we covered back at number seven. Butch started small, committing crimes like cattle theft and petty offenses. But his real claim to outlaw brilliance came on June 24th, 1889, when he and three others robbed the San Miguel Valley Bank in Colorado, escaping with roughly $24,000, about $800,000 today.
The success of that job came down to Butch’s incredible attention to detail. He spent weeks scouting the area, memorizing every escape route, and even had custom leather bags made to handle the weight of the loot. He also set up a relay system of fresh horses positioned along the escape route, ensuring that any pursuers would be left far behind.
Butch left nothing to chance, and that meticulous planning allowed him and the Wild Bunch to pull off bank and train robberies for over a decade. Surprisingly, neither Butch nor the Sundance Kid ever killed anyone during these heists. But eventually, growing pressure from law enforcement forced the duo to flee the country. They ended up in Bolivia, where they got into a shootout with Bolivian soldiers, a battle in which both were reportedly killed.
The two were supposedly buried together in a local cemetery, but in the 1990s, DNA tests on their remains revealed no match to living relatives. That sparked rumors that the men may have survived the shootout, quietly returning to the United States and living out their days in comfort under new identities. They may not have been the most dangerous killers in the West, but when it came to banks, trains, and the government’s most wanted list, there was never a deadlier gang than the Wild Bunch.
If you enjoyed this countdown, you’ll love the video I’ve got right here. The myths of the Wild West Hollywood got completely wrong.