The 30 Most Famous Cowboys (and Cowgirls) of All Time

Source: The Humboldt Star / Wikimedia Commons

25. Billy Stiles (1871-1908)
> Hometown: Casa Grande, Arizona

Stiles was a criminal — robbing banks and trains — and also a lawman, working twice as an Arizona deputy sheriff. While his career as a criminal landed him in jail multiple times, and even forced him to flee the country, his law enforcement work proved to be his ultimate undoing. Stiles was shot and killed in 1908 while serving a warrant.

Source: Karl Walter / Getty Images Entertainment via Getty Images

24. Wylie Gustafson (1961- )
> Hometown: Conrad, Montana

Wylie Gustafson comes from northern Montana and is a fourth-generation rancher and cowboy. A renowned singer and songwriter, Gustafson is famous for his yodeling prowess. Gustafson’s group Wylie & the West have appeared on the Grand Ole Opry 50 times. He has performed on “Late Night with Conan O’Brien.”

Source: Library of Congress / Wikimedia Commons

23. Henry Nash (1869-1902)
> Hometown: Mount Sterling, Indiana

A cowboy from Indiana, Nash went pioneering in Arizona and later rode with Teddy Roosevelt’s Rough Riders volunteer military unit that gained fame during the Spanish-American War. Nash later became a teacher who worked in the Philippines.

Source: H.J. Rogner, Rawlins, Wyo. / Library of Congress

22. Kitty Canutt (1899-1988)
> Hometown: New York City, New York

One of the more colorful cowgirls of the Old West, Canutt, known by the stage name Kitty Wilks, won the women’s saddle bronc championship at the Pendleton Round-Up several times. She also had a turbulent relationship with husband and rodeo cowboy Yakima Canutt. The story goes that Kitty Canutt wore a diamond in her front tooth that she would occasionally hock during hard times.

Source: DrStew82 / Wikimedia Commons

21. Jack Dunlop (1872-1900)
> Hometown: Texas

Like many men in the West, Dunlop, commonly known as “Three Fingered Jack,” turned to a life of crime after working as a cowboy in his late teens. Dunlop joined a gang in the 1890s and robbed trains and banks. After one attempted robbery, he was hit with a buckshot fired by a guard on a train. Dunlop fell from his horse and was taken to Tombstone, Arizona, where he died.