Frederic Remington found inspiration in the roughriders of the American West. He was intrigued by the interaction of the cowboy and his horse and drew both extensively. After living in the West and establishing himself as an illustrator, he returned to New York in 1886 and began working in oils and modeling clay.

In March 1905 the president of the Fairmount Park Art Association suggested that a statue of a cowboy be commissioned for the park. Remington had worked on a small scale until this time and was apparently intrigued by the prospect of a larger work. He drove through Fairmount Park and finally selected a site: a rock ledge jutting out over East River Drive (now Kelly Drive). As the records indicate, the site was "Mr. Remington's choice and not selected until after he got a horseman to pose for him in that exact place." Remington modeled the cowboy on Charlie Trego, a native of Chester County, Pennsylvania, and a friend from his cowboy days in Montana. Installed in 1908, the sculpture is one of the country's earliest examples of a site-specific work. However, it was to be Remington's only large-scale bronze. He died the year after the installation of Cowboy.

Adapted from Public Art in Philadelphia by Penny Balkin Bach (Temple University Press, Philadelphia, 1992).