Nature has long been viewed as an escape, a way to alleviate yourself from the burden of society. Henry David Thoreau, in his seminal work Walden (1854), established a new American tradition for idealizing and interacting with nature, which he portrays as an antidote to modern ills. Sean Penn in his 2007 film adaptation of the John Krakauer nonfiction book, Into the Wild (1996), subverts this notion. While the main subject, Christopher McCandless, is enamored with the Thoreauvian archetype of nature as an escape and antidote to modern ills, he ultimately dies in his pursuit of that Thoreauvian ideal. In the final scene, two years after Chris moved away from home and traveled to the Alaskan Frontier in search of existential meaning, he dies in a bus — a symbol of the remnants of a decaying and unavoidable modern society. In his dying moments, Chris scribbles into his notebook the final words, “Happiness only real when shared.” By using Thoreau as a tool to better understand Chris’s philosophical orientation, this paper will explore Chris’s use of nature as a reprieve from modern society and, finally, reveal the inescapability of that modern society — even in the most remote reaches of Alaska.