Eco-heroic quests for environmental communion continue to be represented, mediated, and glorified through film and media narratives. This paper examines two eco-heroic quests in the Alaskan "wilderness" that have been portrayed in two Hollywood motion pictures: the movies "Grizzly Man" and "Into the Wild". Both films vividly document and re-inscribe heroic status to the stories of Timothy Treadwell ("Grizzly Man") and Christopher McCandless ("Into the Wild"), their tragic encounters with nature, and the pivotal experiences that gave them both eco-heroic identities in the American imagination. As is often the case for Greek and Shakespearean dramas, each hero met a tragic, unnecessary death in Alaskan "wilderness", but in the process reiterated a settler colonial narrative. We argue that an Indigenous-focused Land education and its counter-narratives of holistic relations are sorely needed. It is Indigenous Land education that can break the cycle of Eurocentric celebrations of solitary heroism, rugged individualism, and ignorance of place. In order to forge Indigenous/non-Indigenous relations in our cultural imaginations and to address compounding environmental struggles, we need to turn to Indigenous stories and teachings that are already in place, in deep relation with the Land, water, animals and plants on Indigenous territory. We need to turn to Land education that is currently not in place or acknowledged in environmental education.