Despite limited formal art training, Remington rose quickly from commercial illustrator to painter. He first exhibited at the American Water-Color Society Annual in February of 1887 and then in April of that year was invited to exhibit at the National Academy of Design (NAD), where he continued to exhibit regularly until 1899.

Remington's paintings of the 1890s exceeded all his previous work in ambition, scale, and accomplishment. Exhibiting his paintings in prestigious annual exhibitions, he sought to demonstrate his superiority as a painter. In 1890 he presented twenty paintings at the American Art Galleries, including Past All Surgery (Aiding a Comrade) and An Indian Trapper. Several months later he presented the Clark's Dismounted—The Fourth Troopers Moving the Led Horses at the NAD.