4. Into the Wild (2007)
It couldn’t be. Because (spoiler alert!) the twenty-something adventurer who donated his life savings to Oxfam and spent 100 days exploring the wilds of Alaska died before he could share his story with the world.
What Penn did have was the research and writings of Jon Krakauer, who wrote extensively about the story, first as a feature for Outside magazine and later as a novel.
Whereas Penn’s work as an actor is noted for his often explosive emotionality, as a director he seems to favor quiet intensity. The rather underrated Emile Hirsch turns in the performance of his career as the introspective McCandless, whose journey and lifestyle leanings are inspired by the likes of Jack London and Henry David Thoreau.
The film’s long spans of beautiful silence are interspersed with McCandless’ interactions with those he meets on the road, including retiree Ron Franz (played by Hal Holbrook, who earned an Oscar nomination for the role) who ends up serving as McCandless’ one reason for coming home.
Unfortunately, he never gets the chance.