This dissertation explores how an examination of medieval literature in comparison with Native American literature and the critical and anthropological techniques developed to access it can help to facilitate more balanced and innovative readings of those texts. To that end, this project addresses four different topics. It begins with an exploration of the mystical and visionary literature, specifically in The Book of Margery Kempe, and compares the way her text has been received and perceived in contrast with the reception of the recorded mystical experiences of Black Elk and Handsome Lake, two well-known Native American visionaries. This is followed by an examination of the role of the trickster figure in the works of Chaucer, particularly in The Canterbury Tales, with attention to how the archetypal characteristics of this anthropologically determined construct can help shed light on some of Chaucer’s most complex works and themes. This argument is further divided into three sections. The first portion deals with the introduction and descriptions of the final group of Pilgrims in the General Prologue who most closely conform to the archetype. This is followed by a consideration of how their individual tales and the frame narratives surrounding them invoke the qualities of trickster discourse. Chapter four explores Chaucer’s deployment of birds in his works, specifically as they embody qualities of the trickster and complicate and even undermine the transmission of language and meaning. The fifth chapter compares the Arthurian matter of Britain, particularly the texts of Geoffrey of Monmouth, Wace and Layamon to the resistance narratives contained in Black Elk Speaks and other accounts of the Battle of Little Big Horn to establish how such works can be appropriated by the very colonizers they depict resistance to. The sixth and last chapter explores the essential term of savagery and the relationship between the Icelandic sagas and their depiction of the inherent violence and otherness of both the Skrælings and the Vikings who encounter them.