From childhood, he was a sketcher, but it wasn't until a horse fell on him that he considered art as a career. In the hospital recovering from his injuries, he saw reproductions of Russell's paintings in a magazine, and that exposure set his career of portraying the lives of cattlemen.

He worked as a cowboy in Colorado, Arizona, and California until he was 21 and then enrolled in Chicago at the Art Institute and the American Academy. In 1936, he moved to New York City to work as a magazine illustrator and took lessons from Harvey Dunn, known as a great illustrator. He also worked with Felix Schmidt in a commercial studio.

Dye was a successful illustrator in New York, doing assignments for "Saturday Evening Post," "Argosy," "Outdoor Life," and "The American Weekly." However, a trip to California alerted him to how little quality Western art existed, and he soon began vacationing and painting in the West, finally establishing a studio in Denver, Colorado and becoming a partner in the Colorado Institute of Art.

Because of the wide acceptance of his painting, he gave up teaching and illustrating and in 1960, moved to Sedona, Arizona, where he gained recognition for his oil paintings of western scenes. In 1964, he, Joe Beeler, and John Hampton organized the Cowboy Artists of America, and he was the second president. The group is devoted to the painting and sculpture tradition of Charles Russell and Frederic Remington and began with artists who not only depicted cowboys but were working cowboys themselves.