12 Incredible Real Life Cowboy Duos

The Wild West is one of the most romanticized periods in film. In the golden era of the '30s through the '60s when actors like John Wayne ruled supreme, the idea of the rugged frontiersman, the cowboy and outlaw was unparalleled in popularity.

Some incredible and iconic actors have been known to play notorious outlaws. The characters were usually bloodthirsty criminals, but people like Paul Newman, Robert Redford, Val Kilmer, and Kurt Russell lent these would-be villains a romanticised, folk-hero quality. Thanks to Hollywood, some of the most famous cowboys have become legends.

The truth of cowboy life, however, was much grimmer. The infamous outlaws that these actors portrayed were real-life criminals, murderers, and thieves. Yet, some of the greatest friendships - or 'bromances', if you will - that have ever been recorded developed between these cowboys. The profound connections between these adventurous characters help keep these cowboys, cowgirls, and outlaws alive in our hearts and minds. These are the twelve most famous cowboy duos that have ever existed.

12 King Fisher and Ben Thompson

King Fisher and Ben Thompson

King Fisher was a Texan gunslinger who was first arrested for horse theft at the age of 16. He became a cowboy and outlaw after taking part in posse activities around Texas ranches, and became proficient with his ivory handled pistols. He lived a very different life than Ben Thompson, who was an English-born gunman, gambler, and sometimes-lawman. Thompson once made an acquaintance of John Wesley Hardin, one of the most notorious gunmen in the Wild West, and tried (and failed) to remove “Wild Bill” Hickok as marshal of Abilene, Kansas, with Harden’s help.

Fisher and Thompson probably met in the early 1880s. In 1884, while in San Antonio, Texas, Fisher met up with his old friend Thompson. Thompson was unpopular in San Antonio because he had killed a popular theater owner there named Jack Harris, and a feud over the killing had been brewing. Thompson wanted to smooth things over with another theater owner and friend of Harris’, named Joe Foster.

Fisher accompanied Thompson to a theater production, but Foster refused to speak with them in their theater box. Fisher realized something was not right. As Fisher and Thompson stood up to leave, two gunmen in another theater box ambushed Fisher and Thompson, opening fire and killing them. The gunmen were not prosecuted, and the event came to be known as the Vaudeville Theater Ambush.

11 “Texas Jack” Vermillion and “Soapy” Smith

Soapy Smith

John “Texas Jack” Vermillion was a Confederate soldier in the Civil War, then a lawman, and then an outlaw. The origin of his nickname, “Texas Jack,” is unknown, but when asked why that was his nickname, he famously replied, “Because I’m from Virginia.” He took part in the 'Earp Vendetta Ride' that was glorified in the movie Tombstone, and afterwards joined the Soapy Smith Gang in Denver, Colorado.

Jefferson “Soapy” Smith was a famous con artist and crime boss, who gained his sobriquet “Soapy” after his most famous scam - a prize-package soap-selling racket. He was known for his swindles all across the US, including rigging city and state elections and cheating clientele in gambling halls he ran.

Texas Jack was with Soapy in 1889 at an Idaho train depot when a rival gang tried to assassinate Soapy. In 1898, Soapy tried to rob a man of $2,700 worth of gold (around $80,000 today) in a game of three-card monte, and the next day he was fatally wounded in a gunfight known as the Shootout on Juneau Wharf. Texas Jack either drowned in 1900, or died peacefully in 1911.

10 Bob and Gratton Dalton

Dalton Gang Killed - Bob and Grat in the middle

Grat Dalton and Bob Dalton were younger brothers of famed Deputy US Marshal Frank Dalton. When Frank was killed during a shootout with outlaws, the Dalton brothers were devastated. Gratton became the new Deputy Marshal, but quickly sought an easier way to make a living, and thus formed the Dalton Gang.

The Dalton Gang robbed trains, but never struck it rich. In 1892, they decided to perform a bank robbery in Coffeyville, Kansas. The robbery was a colossal mistake, as townsfolk recognized the gang coming into town, and when they were ready to flee, they were surrounded. A shootout erupted, and both Gratton and Bob were killed, as well as four other Dalton Gang members, and four townspeople.

Brother Emmett Dalton was shot 23 times but somehow survived, and three other townspeople lived. The Dalton Gang was short lived and ultimately non-productive.

9 Bill Dalton and Bill Doolin

Bill Doolin didn't quite make it

The fame that came from the Coffeyville shootout made the Dalton’s posthumously famous, and drove younger brother Bill Dalton to become more famous than his brothers. He co-founded the Wild Bunch gang with Bill Doolin, and for three years they gained a name for themselves doing bank robberies, stagecoach robberies, and train robberies.

The Wild Bunch was the most famous outlaw group in the Old West for a time. They were part of a shootout against 14 lawmen, but in late 1894, Bill Dalton was killed by US marshals. Rewards were offered for the rest of the Bunch’s capture or death, which turned friends into foes.

Doolin fled to New Mexico, but was relentlessly pursued by the Three Guardsmen, an emphatic group of lawmen. In 1896, Doolin was captured by one of the Guardsmen, Bill Tilghman, but escaped. He took refuge with his wife in Oklahoma Territory, but was killed by another guardsman, Marshal Heck Thomas, on August 24, 1896.

8 “Flat-Nose” Curry and “Kid Curry” Logan

Kid Curry with wife Della Moore

George “Flat-nose” Curry and Harvey “Kid Curry” Logan were both part of Butch Cassidy and the Sundance Kid’s group, the Wild Bunch (named after the original Wild Bunch formed by Bill Dalton and Bill Doolin). Both Curry and Logan took part in an escape after a Wild Bunch train robbery, and together killed a pursuing marshal. They were good friends in the Wild Bunch, and when George Curry was killed by a Sheriff in 1900, Kid Curry vowed revenge.

Kid Curry has been referred to as “the wildest of the Wild Bunch,” and reputedly killed at least nine lawmen in five different shootings, and two men in other instances. After George’s death, he rode to Utah to avenge his mentor’s death (he took George’s surname, Curry, because he looked up to him so much) and killed the Sheriff and Deputy Sheriff in a gunfight. He rode with the Black Jack Ketchum gang, and formed his own gang before joining the Wild Bunch.

Kid Curry was captured in a pool hall in Knoxville in 1902, but escaped afterwards (with a rumor spreading that a deputy had received $8,000 to let him go). In 1904, he was tracked down by a posse, outside of Parachute, Colorado. He had stolen horses to escape a train robbery, and the horse-owner and his neighbors pursued Curry, wounded him, and then Curry shot himself in the head. Rumors spread that Curry did not kill himself, was misidentified, and departed to South America with Butch Cassidy and Sundance.

7 Johnny Ringo and “Curly Bill” Brocius

Johnny Ringo and Curly Bill in Tombstone

Johnny Ringo and “Curly Bill” Brocius were portrayed in the movie Tombstone as the bad guys. It could be said that all outlaw cowboys were “bad guys,” but there’s a big gray area as to what constitutes 'bad.’ They are both mainly portrayed as being enemies of the Earp brothers, and participating in youngest brother Morgan Earp’s assassination.

As part of a group simply known as ‘The Cowboys,' Curly Bill and Johnny Ringo took part in many robberies and gunfights together, including a revenge-killing after one of their friends was killed, the infamous shootout at the O.K. Corral, and the subsequent 'Gunfight at Iron Springs.’ During that particular shootout, Curly Bill was struck down by a shotgun blast to the chest from Wyatt Earp.

Later that year, on July 14, 1882, Johnny Ringo was found dead in West Turkey Creek Valley, with a bullet hole in his right temple. Doc Holliday was originally assumed to be his killer, but modern studies believe Ringo committed suicide due to being depressed, drunk, and the recent deaths of his outlaw friends.

6 “Buffalo Bill” Cody and Annie Oakley

William “Buffalo Bill” Cody was one of the more colorful figures of the Old West. In 1883, he started a traveling show called Buffalo Bill’s Wild West, and would tour the country as the Cirque du Soleil of the time. It was during this time that he met Annie Oakley, an amazing sharpshooter who would become one of the first American women to reach “superstar” status.

Buffalo Bill also traveled in a show starring “Wild Bill” Hickok for 10 years, and his touring circus-like attraction gave him immense wealth. Oakley gained notoriety for beating a bravado marksman, Frank E. Butler, in a shooting match, at just 15 years old. Butler lost about $2,500 in today’s money, but he ended up marrying Oakley a year later.

Oakley and Butler joined Buffalo Bill’s Wild West in 1885. Oakley would go on to earn more than any other performer in the show, other than Buffalo Bill himself.

5 Billy the Kid and Tom O'Folliard

Billy the Kid

Billy the Kid is, of course, one of the most famous cowboys of the Old West - seen as both a notorious outlaw and a folk hero. William H. Bonney (which was actually William McCarty), as he went by, was relatively unknown during his life. Tom O'Folliard was Billy’s best friend, and they were both members of the outlaw group The Regulators, and took part in the infamous Lincoln County War.

The Lincoln County War arose from a conflict between two factions, over control of dry goods trade in the New Mexico Territory. The Regulators backed the newer, competing trade-story of the Tunstall-McSween faction, who were allied with a posse of outlaws and lawmen against the older organization of the Murphy-Dolan faction. The conflict was marred by back-and-forth revenge killings, climaxing with the Battle of Lincoln, which was a five-day gunfight.

O'Folliard was shot and killed by Pat Garrett’s posse (a marshal on the side of the Murphy-Dolan faction) in 1880, in a midnight ambush that Billy the Kid barely escaped. Soon after, the Kid’s group were surrounded by Garrett in an abandoned building, and Billy was captured. He was scheduled to be executed, but stunned everyone when he escaped prison by killing both of his guards. Sheriff Pat Garrett followed the Kid to Fort Sumner, where he eventually found and killed Bonney three months after his escape.

4 “Wild Bill" Hickok and “Calamity Jane”

James Butler Hickok was a soldier and spy for the Union Army, and then a lawman, gunslinger, and professional gambler. He was involved in several notable shootouts, including one with Davis Tutt in the first ever “quick draw fuel,” and he was killed while playing poker in Deadwood, South Dakota, by the unsuccessful gambler Jack McCall.

Martha “Calamity Jane” Canary was a frontierswoman and scout. She claimed to have been married to Wild Bill, but divorced him so he could marry Agnes Lake. She was famous for being compassionate to the sick and needy, and for her (supposed) military campaigns against Native Americans. Even if all of her claims are false, she at the very least traveled with Hickok to Deadwood, and from Deadwood their fame as partners became legend.

3 Frank and Jesse James

Jesse (L) and Frank James (R)

Frank James was the older brother of the infamous outlaw Jesse James, and the co-founder of the James-Younger Gang. Frank was a Confederate in the Civil War. His brother, Jesse, was already a celebrity during while he was alive, but became a legendary figure after his death. After the war, the duo gained notoriety by robbing banks, stagecoaches, and trains.

The James brothers were most active with their gang for 10 years, from 1866 until 1876, when their attempted robbery of a bank in Northfield, Minnesota, ended with the death of most of the gang. Only Jesse and Frank were left alive and uncaptured. After Jesse’s name was given a $5,000 bounty, he was betrayed and killed by his trusted friend, Bob Ford, and his death became a national sensation.

Ford was shocked to find himself arrested for first degree murder and sentenced to hanging, but he was pardoned and received a small part of the bounty just two hours after his sentencing. He would go on to star in a touring stage show with his brother, where they re-enacted the shooting. Frank James surrendered to the governor of Jefferson City, Missouri, in 1882, was acquitted of his crimes, and released. He lived with his mother for the next 30 years, and died at the age of 72.

2 "Doc" Holliday and Wyatt Earp

Wyatt Earp, one of the middle brothers of the Earp family, is probably the most famous Old Western lawmen of all time. He was the central figure of the Gunfight at the O.K. Corral, and was a major figure in the development of Tombstone, Arizona. He was a lifelong gambler, always moving from town to town, and he was also one of the longest lasting cowboys, living until the age of 80.

John Henry “Doc” Holliday was Wyatt’s friend, and a gambler, gunfighter, and dentist. He partook in the Gunfight at the O.K. Corral - as a lawman - in which three cowboys were killed. He also joined Wyatt in the Earp Vendetta Ride after Wyatt’s younger brother Morgan was murdered by Curly Bill Brocius and his group. He died of tuberculosis at the age of 36. Both Wyatt Earp and Doc Holliday are two of the most highly-romanticized cowboys to come out of the Old West.

1 Butch Cassidy and The Sundance Kid

Sundance Kid (seated left) and Butch Cassidy (seated right)

In all fairness, Butch Cassidy’s best friend was fellow co-founder of the Wild Bunch, Elzy Lay. Nonetheless, his and Harry “Sundance Kid” Longabaugh’s friendship is immortalized by Paul Newman and Robert Redford’s portrayal of them. Together, with other members of the Wild Bunch gang, they performed the longest string of successful bank robberies in American history.

After taking part in numerous bank robberies and failing to get amnesty, Cassidy and Longabaugh fled to South America, along with Longabaugh’s girlfriend Etta Place. The duo held up a bank in Argentina, which proved to be their most lucrative yet - escaping with a sum of about $100,000 in today’s money - and then they vanished to Bolivia. That is where their famous final stand took place, in which they became surrounded by lawmen, and (probably) committed suicide.

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