Most Famous Cowboys of All Time

Source: The Humboldt Star / Wikimedia Commons

26. Billy Stiles (1871-1908)
> Hometown: Casa Grande, Arizona
> Wikipedia page views: 6,325

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 killed in 1908 while serving a warrant.

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

25. Kitty Canutt (1899-1988)
> Hometown: New York City, New York
> Wikipedia page views: 8,667

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: Wylie Gustafon / Getty Images

24. Wylie Gustafson (b. 1961)
> Hometown: Conrad, Montana
> Wikipedia page views: 9,829

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: DrStew82 / Wikimedia Commons

23. Jack Dunlop (1872-1900)
> Hometown: Texas
> Wikipedia page views: 11,923

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 buckshot fired by a guard on a train. Dunlop fell from his horse and was taken to Tombstone, Arizona, where he died.

Source: Willis Kent Productions / Syndicate Pictures / Wikimedia Commons

22. Montie Montana (1910-1998)
> Hometown: Wolf Point, Montana
> Wikipedia page views: 14,211

Montie Montana was a beloved cowboy figure in Southern California who appeared at events and parades in sequined western attire. Montana was a real-life cowboy who learned roping tricks as a child growing up in Montana. He moved to California and parlayed his roping skills into a career in movies. He also lassoed President Dwight Eisenhower — with the president’s approval — during the inaugural parade in 1953.