This project explores the parallels between the journeys of Dante’s Pilgrim in Inferno and Frodo Baggins in The Lord of the Rings. It asserts that these two examples are a variant of the hero’s journey, more akin to a divine pilgrimage. Through this analysis, each author’s use and repurposing of mythology and monsters to fit within a Christian narrative will be closely examined. Following the Pilgrim and Frodo, this project charts their voyages through hell (or hellish landscape) and the effects that has on each of them psychologically and spiritually. In essence, this project seeks to chart both external and internal movement of these two characters as they traverse hellish landscapes. In doing so, it is important to also examine those who seek to guide our characters through their monumental task. Lastly, the taking on of sin, the bearing the weight of the world is a component that plays a major part in each character’s internal arch and through the close reading of this process, gain an understanding of how the authors’ view individual strength, devotion, and the overcoming of evil