Top Five Infamous Old West Cowboys

What is the definition and and proud of history of The American Cowboy? Enjoy this informative article as it relates to everyone living the Western Lifestyle.

By Krysta Paffrath 

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The term “cowboy” has been used throughout American history for decades. In reality, the word “cowboy” comes from Spain, tracing its roots to the Spanish word “vaquero”. There are different words that have stemmed from “cowboy”, usually meaning the same thing, some of these variations include cowpoke, buckaroo, cowpuncher commonly used in Texas, and cowhand.  The true definition of a cowboy is deemed to be a cattle herder who tends to their cattle while on horseback. But, thanks to the western movie genre and Hollywood, “cowboy” has taken on a life of its very own. Here we are excited to take a stab at our top five picks for True American Cowboys.

Billy the Kid

By far the most well known outlaw cowboy was Billy the Kid. Best known for being the youngest outlaw of his time and narrowly escaping nearly every situation he got himself into. Henry McCarty or William H. Bonney depending on who you talk to, born on September 17 or November 23, 1859, was an outlaw and gunfighter of the American Old West. No matter which way you look at it, Billy the Kid was a much feared cowboy. He was orphaned at age 14 and had to figure out a way to provide for himself and the outlaw life was the path he chose. By the time he was shot and killed at age 21, he had killed at least 8 people that historians know of. The legend of Billy the Kid has stood the test of time. 

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Billy the Kid, thought to be pictured in the middle.

Butch Cassidy

Butch Cassidy, born Robert LeRoy Parker in 1866, was a classic western outlaw who is best known for robbing trains and running with his gang, the “Wild Bunch”. How did he receive the infamous name “Butch Cassidy”? Well, here is how historians say it happened. As a teenager, while working on a dairy ranch, “Butch” met Mike Cassidy, a horse and cattle thief, who would later become his friend and mentor. After meeting Mike, Butch worked on several ranches, in addition to a brief apprenticeship with a butcher in Rock Springs, Wyoming, where he received the nickname, “butcher”, which morphed later into ”Butch”. He later added the last name Cassidy in honor of his old friend and mentor. After Butch got tired of running from the law, he and two others fled the country for good and his days of outlawing supposedly ended in a shootout in Bolivia.

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Annie Oakley

Some of the best cowboys are actually cowgirls and Annie is no exception. Born with the name Phoebe Ann (Annie) Mosey, in 1860, this young girl couldn’t have had any idea of the impact she would have later in life. Annie Oakley is most famously known for being a sharpshooter and entertainer, but she represented much more than that. At the age of seven, she started trapping and by eight she was hunting to pay her family’s mortgage, which she did successfully by selling wild game to local hotels and restaurants. Her world changed on Thanksgiving Day 1875. She was 15 and was challenged to a shoot-off with marksman and entertainer Frank Butler. That was the start of Annie’s long career and she married Frank a year later. Annie was said to have taught over 15,000 women on how to use to a gun, stating, “I would like to see every woman know how to handle guns as naturally as they know how to handle babies.” She went on breaking records, even at the age of 62, and fighting for women’s rights well ahead of her time. Annie passed at age 66.

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Calamity Jane

You should start seeing a trend between these outlaws real name versus the name that history buffs know them as. Maybe not the most popular, but definitely on of the most memorable is the great, Calamity Jane. She wasn’t pretty or well educated but she marched to the beat of her own drum. Martha Jane Canary, born May 1, 1852, better known as Calamity Jane, was an American frontierswoman known for being a friend of Wild Bill Hickok. She is said to have exhibited compassion to others, especially to the sick and needy. This side of her character contrasted with her outlandish ways and helped to make her a decorated frontier figure.

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Buffalo Bill

Rounding out this top five infamous old west cowboys is the one and only Buffalo Bill. Born with the name William Frederick, on February 26, 1846, he was most known for being an American soldier, bison hunter, and showman. At the age of 11, Buffalo Bill started working after his father’s death. At age 15 he started riding for the Pony Express and later joined the Army, serving in the Civil War for two years. While he was a decorated veteran, this legend began to spread when he was only 23. Shortly thereafter he started performing in shows that displayed cowboy themes and episodes from the frontier and Indian Wars. He founded Buffalo Bill’s Wild West in 1883, taking his large company on tours in the United States and, beginning in 1887, in Great Britain and continental Europe.

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