Will Rogers was a respected writer and cowboy entertainer whose work embodied and demonstrated the traditions and values of the American cowboy.  The Will Rogers Medallion Award was originally created to recognize quality works of cowboy poetry that honored the Will Rogers heritage, but has expanded to include other works of Western literature and film.
 

The awards competition takes place annually, and the awards ceremony was held every fall for over twenty years in Fort Worth, Texas. In 2025, the award weekend officially moves to Will Rogers' hometown of Claremore, as well as neighboring Tulsa, Oklahoma.