5 Sam Bass
Sam Bass may not have been the most well known outlaw but he gets his name on the list because he pulled off the same crimes that the James-Younger Gang and the Wild Bunch did only his first one outdid them all. In his very first robbery that we have on record, Bass and his accomplices stole $60,000 from the Union Pacific gold train from San Francisco. It was the all-time largest robbery of a Union Pacific train. Bass and his gang continued their activities and despite never netting more than $500 at a time, they got the attention of the Pinkerton agents. They took the sick father of Jim Murphy, a member of Bass’ gang, into custody, forcing Murphy to become an informant. And so in 1878, Sam Bass and his gang were ambushed and he was shot and killed at the age of 27.
4 The James-Younger Gang
We’re cheating a bit here because it seems unfair to give all the infamy to Jesse James. The gang was made up of former Confederate soldiers and guerilla fighters, many of whom were already notorious for war crimes, including Frank and Jesse James. The two brothers joined Cole Younger and his brothers and began a series of daring robberies of trains and banks. They got so good that they sometimes even got theatrical. The James brothers specifically were known for their discipline and attempts to leave train passengers alone while stealing primarily what was in the train safe. That is probably the source of the Robin Hood image, along with a series of newspaper columns about the gang’s exploits written by a fellow ex-confederate. Eventually, it failed them however. The gang bungled an operation and only the James brothers got away. Frank settled down to a quiet life on the straight and narrow but Jesse wasn’t interested. He tried to get together a new gang but eventually was betrayed and killed by one of his own who was after the reward money.
3 Belle Starr
Myra Maybelle Shirley Reed Starr played piano and was a graduate of the Carthage Female Academy and her knowledge came to good use. For example, she always rode sidesaddle and wore a black velvet riding habit and plumed hat. Obviously this was in addition to the two pistols she carried and the cartridge belts across her hips. Her first husband, Jim Reed, was involved with a number of outlaw bands, including the Starr family. After Jim’s death, Belle married Sam Starr, a Cherokee Indian. She settled down very happily in Indian Territory where she managed a lucrative operation of cattle rustlers, horse thieves and bootleggers and earned the title Queen of the Oklahoma Outlaws. Her death is almost as mysterious as those of Butch Cassidy and the Sundance Kid. She was shot twice at the age of 40 on the way home from visiting a neighbor and to this day nobody can say why or even by whom.
2 Butch Cassidy and the Sundance Kid
Although their gang was actually called the Wild Bunch, Robert Leroy Parker (aka Butch Cassidy) and Harry Alonzo Longabaugh (aka The Sundance Kid) really got their notoriety as a pair when they escaped from the law and eventually were killed in a shootout in Bolivia. Their gang was known for robbery of banks, trains and company payrolls and although they were involved in shootouts with lawmen neither was ever actually charged with murder. But the Pinkerton Detectives were after them and they eventually escaped, along with Longabaugh’s girlfriend and Etta Place, to Argentina to begin a quite life of ranching. But only a few years later the three were back to their standard robberies of banks and payrolls. The Sundance Kid eventually escorted Etta Place back to the States but quickly returned to rejoin Butch Cassidy for one more attempt to walk the straight and narrow. But in 1908 in Bolivia, two masked Americans stole the payroll of a mining company in the area and the police were quickly tipped off. They gathered the mayor, the police and soldiers that were stationed nearby and a shootout ensued. The two American bandits were discovered inside their house riddled with bullet holes, including final holes in their heads that made it appear that one gave his wounded accomplice a mercy shot and then killed himself. They were buried in unmarked graves which haven’t been found and so there’s no proof that Butch Cassidy and the Sundance Kid ever really went down.
1 Billy the Kid
William Henry McCarty, Jr. went by a number of names but got his most famous one from his young age, even younger looking face and his fun-loving personality. Despite being arguably the most notorious outlaw of the Wild West, he got his start in crime stealing cheese and later being found in possession of goods that had actually been stolen by a fellow boarder. He escaped from jail and drifted around the west as a ranch hand, horse thief, cattle rustler and cattle guard. In New Mexico, Billy got caught up in a local feud that was known as the Lincoln County War. The new governor of New Mexico, Lew Wallace, promised an amnesty for those involved but Billy didn’t qualify. Nonetheless, Wallace said he would cut a deal but ended up abandoning the Kid in jail. Billy the Kid escaped and spent the next couple of years on the lam, rustling cattle and running from the law. He was even caught after a dramatic siege but once again managed to escape from prison. Only a few months later however, he was finally cornered and shot by Sherriff Pat Garret at the ripe old age of twenty one.