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The Baddest Country Outlaws

Country music has always been connected with cowboys roaming the vast expanses of the Wild West. But it comes as no surprise that plenty of these cowboys were outlaws.

You don’t have to support robbing trains, having shootouts at high noon, or causing a brawl over a hand of cards, but you can still admit that these gunslingers are a fascinating bunch.  Here are some of the most interesting bandits from back in the day.

Billy the Kid (1859 – 1881)

Billy the Kid OutlawUsually a nickname like “the Kid” wouldn’t give someone such a rough reputation, but Billy managed to pull it off.  Born as Henry McCarty, he alternated between fighting in the Lincoln County War in New Mexico, and simply wreaking havoc around the region.  His life was surrounded by rumors, and there have been many exaggerated tales about how many people he killed and when he actually died.

Henry Newton Brown (1857 – 1884)

Harry Newton Brown OutlawNext up is one of Billy’s buddies.  After roaming around with the Kid, Brown eventually retired from a life of crime to become a deputy sheriff.  However, strapping on a badge doesn’t automatically change a man, and he gained a reputation for picking fights with drunks.

It wasn’t long before people turned on him, but it’s hard to tell if the townsfolk didn’t like their lawmen stirring up trouble, or if they thought it wasn’t sporting to pick on those who’d had a few too many whiskeys.  Most likely it had something to do with a bank robbery he was involved in, and his coffin was built after a mob lynched him.

Sam Bass (1851 – 1878)

Sam Bass OutlawThis is another outlaw who tried to start life as a law-abiding citizen, but eventually learned that fate had other things in store for him.  Things mostly went wrong when he and his partner stole the herd of longhorns they were transporting, but it helped give him some money to use at the card tables.  Unfortunately, the rush of gambling eventually led to bigger and more elaborate stagecoach and train robberies.  He even managed to pull of the largest robbery of the Union Pacific Railroad, before catching a bullet.

Felipe Espinosa (1836 – 1863)

This outlaw killed so many people that he’s often thought of as America’s first serial killer.  His life took a bad turn after the Mexican-American War, and he and his brother managed to kill 32 people to try and settle the score.  Eventually a tracker named Tom Tobin hunted them down, but shooting them dead wasn’t enough, and the outlaw’s heads were even cut off.

Belle Starr (1848 – 1889)

Belle StarrIt’s not often that a rich girl abandons her comfortable city life to become an outlaw, but Myra Maybelle Shirley Reed Starr was far from ordinary.  The Civil War disrupted her life, and her talent with a gun helped her get in with some big outlaws of the time.  She eventually became known as the Bandit Queen.

Hoodoo Brown (1856 – ?)

Hoodoo was originally named Hyman G. Neil but this obviously had to change before starting a life of crime.  He didn’t like the lawless state of Las Vegas, New Mexico, so he imported some gunslingers and started the Dodge City Gang to protect the town.  However, these trigger-happy men eventually started defining their own laws, and they simply turned into the biggest band of outlaws around.  There are various versions of how he met his end, so he seems to have been another to ride off into the sunset.

Doc Holiday (1851 – 1887)

Doc HolidayHenry “Doc” Holiday spent more time enforcing the law than he did breaking it, but he had enough questionable events throughout his life to land on this list.  Before he was a gunslinger, he was a dentist in Atlanta, Georgia.  Unfortunately, he was eventually diagnosed with tuberculosis, and he was advised to head west to for the dry climate.  Gambling became a habit, and the Wild West did the rest.

Jim Miller (1866 – 1909)

Jim MillerMost outlaws loved having unhealthy habits, but this one didn’t smoke or drink. He even attended church regularly enough to get the nickname Deacon Jim, however it seems the priest never directly asked if he was a professional assassin.  His hands were fast enough to win about a dozen gunfights, but they weren’t enough to stop an angry mob upset about his assassination of a U.S. Marshall.

Bonnie and Clyde (1910, 1909 – 1934)

Bonnie and ClydeEveryone loves a good love story, but Romeo and Juliet have to step aside for Bonnie and Clyde.  These two were the most recent, and they were roaming around causing trouble during the Great Depression.  Much of their reputation was blown up by the media, but they did spend a fair amount of time robbing banks and gas stations.  Unfortunately, they shot a few too many policemen and civilians to get away with it.

Butch Cassidy (1866 – 1908) and The Sundance Kid (1867 – 1908)

Butch and Sundance OutlawsBefore Paul Newman and Robert Redford snagged these roles, these were real guys by the names of Robert Leroy Parker and Harry Alonzo Longabaugh.  Their home base was the Hole-in-the-Wall Ranch in Wyoming, and they held the American record for the longest streak of bank and train robberies.  They even made their escape to Argentina and Bolivia before the law finally caught up with them.

Jesse James (1847 – 1882)

Jesse James OutlawThis member of the James-Younger Gang was a big part of their successful string of train, stagecoach, and of course, bank robberies.  He’s often looked at as a sort of Robin Hood of the Old West, but there isn’t much proof to that whole concept.  Unfortunately, his success led to a widespread reputation, and he was shot in the back of the head by one of his friends who wanted to collect the reward.

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