On the eve of the Civil War in 1858, William S. Prettyman was born in Princess Anne County, Maryland.  Growing up with the turmoil of war surrounding him, it seems a restless spark was lit in Prettyman and would be his companion throughout his life.  Like many young men of his generation he was drawn westward and in 1879 he had settled in Arkansas City, Kansas, directly on the edge of Indian Territory.  He arrived with very little but found work as a photographer’s apprentice, under the guidance of I.H. Bonsall, a well-known war photographer. Prettyman learned the trade and soon opened his own studio.

Prettyman became intrigued by many of his patrons from the Indian Territory, especially members of the Osage tribe.  Prettyman’s curiosity and restless spirit spurred him to find out more about American Indian groups outside the confines of his photography studio.  In 1883 he began an annual tradition; he packed his camera and equipment and journeyed through Indian Territory.  Over the next decade he met, befriended, and photographed people of the Osage, Ponca, Otoe, Iowa, Sacs, Cheyenne, Arapahos, Shawnee, Cherokee, and Potawatomi.  Prettyman was a unique traveler, he not only made friends among American Indian groups but also cattlemen from Texas and the growing numbers of would-be settlers.  His ease of travel between these different groups was reflected in his photography, preserving a cross-section of this diverse region.