Born in Flemingville, New York, Henry Cross became a reputed painter of Indian portraits and racehorses and was described by Buffalo Bill Cody as the "greatest painter of Indian portraiture of all time." He was a perpetually adventurous person who as a teen ran away several times to join the circus, and at age sixteen, traveled to Paris where he studied with animal painter Rosa Bonheur between 1853 and 1855.
Returning to the United States, he earned living painting animals on the sides of wagons and continued to travel West while working with the circus. This is where Cross would first encounter Native Americans, and his experiences during this time stimulated his interest in Western themes. In 1862, after having had a portrait studio in Chicago for two years, Cross moved to Minnesota during the Sioux uprising. During this period, he also learned to speak the Sioux language and painted a portrait of Sioux Chief Red Cloud.
Cross left a rich legacy of portrayals of Native American genre and their interaction with white military civilization. I the 1880s he began to paint Native American ceremonies and in the 1890s visited Hopi pueblos in Arizona, painting depictions of their Snake Dance. The Gilcrease Institute of Tulsa, Oklahoma has one of the most comprehensive collections of his Indian Chief portraits, and other collections are in the Chicago Historical Society and the State Historical Society of Wisconsin.