This chapter focuses predominately upon Will Rogers’ beginnings as a young man seeking his purpose in life. It is during his journey to South Africa that young Will transitions from a ranch hand to a cowboy entertainer. Will’s first opportunity as a professional entertainer was with Texas Jack’s Wild West Show where he was quickly dubbed the “Cherokee Kid.” The Cherokee Kid as an Indian Cowboy provided Will new opportunities to transition as a boy from Indian Territory to a world traveler and popular cowboy entertainer.