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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.

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. Today, we are excited to go through our top five picks of True American Cowboys.

Billy the Kid

Our first favorite goes to the one and only, Billy the Kid. Best known for being the youngest outlaw of his time and narrowly escaping every situation he got himself into by the skin of his teeth. 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 the real deal. 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. There is a lot of skepticism around his death, whereabouts, and photos of him because no one has any real answers. The legend of Billy the Kid will forever stay in America’s hearts as one of the youngest outlaw cowboys of his time.

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”. You might be wondering then, how he came to get the infamous name “Butch Cassidy”, well here is how it happened. As a teenager, while working on a dairy ranch “Butch” met Mike Cassidy, a horse and cattle thief, and he didn’t know it then but friend and mentor. After meeting Mike, he worked on several ranches, in addition to a brief apprenticeship with a butcher in Rock Springs, Wyoming, where he got the nickname, “butcher”, which morphed later into ”Butch”, to which he soon 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 supposedly ended in a shoot out in Bolivia.


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 would have no idea the impact she would have later in life. Annie Oakley is most famously known for being a sharpshooter and entertainer but she stood for much more than that. At the young 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, in 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 about 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.


Calamity Jane

You should start seeing a trend between these outlaws real name versus the name that we all know them as. Once again, maybe not one of the most popular, but definitely memorable is the great, Calamity Jane. She wasn’t pretty or well educated but she marched to the beat of her own drum and that is something that got her in our top five. 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’s. 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. While she may not have the background as some of our other picks, Jane did make a name for herself in the limelight, performing in several wild west shows from 1896 to 1901.


Buffalo Bill

Rounding out our 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 young 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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Hi everyone! I'm Krysta Paffrath, I am a proud Arizona native who has a passion for everything business and rodeo. I am beyond thrilled to be the Editor in Chief for Cowboy Lifestyle Network. With my background in digital marketing and rodeo, this was a natural fit for me to join the team. My adventurous and entrepreneurial spirit has guided me to work in many places like the WYO Quarter Horse Ranch in Thermopolis, Wyoming, a working cattle ranch in Seligman, Arizona, and many places in between. I am passionate about preserving the western way of life and working with different brands and rodeos to make that happen. If you're looking for a write-up, please shoot me an email at Learn more about me at Looking forward to hearing from you!

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