I’m not destitute. I’m living like this by choice.
—Chris (Emile Hirsch)

Sean Penn has found the movie he had to make. Into the Wild, based on Jon Krakauer’s nonfiction bestseller, revisits themes familiar from his previous work as actor and director—loss, grief, and rebellion. Underlining their intimate, ineluctable connections, the film renders such familiar ideas in grand landscapes and excruciating details, revealing their strangeness for Christopher Johnson McCandless (Emile Hirsh).

The movie offers up several views of Chris, most prominently his own (in journal entries appearing as text on screen) and his sister Carine’s (Jena Malone). Where his version begins with his entry into the last place he would live, Alaska (“I now walk into the wild”), hers takes us back to Chris’ graduation from Emory University in 1990. While she sits in the audience with their father Walt (William Hurt) and stepmother Billie (Marcia Gay Harden), Chris mounts the stage to accept his diploma, a ritual that pretty much ends the young man’s affiliation what he considers corrupt civilization. His family, smiling contentedly, can’t know that soon Chris will leave them all behind and, 113 days after his departure, be found dead of starvation inside a “magic bus” where he finds shelter in Alaska.

He leaves behind as well a record of his anguish and exultations. The movie makes smart use of that record as translated by Krakauer, cutting back and forth in time, embedding stories within one another, and so challenging common notions of subjectivity and identity. Chris begins this process, certainly, when he abandons his belongings and donates his small savings ($25,000) to charity, leaves Virginia (where his parents live), and adopts the name “Alexander Supertramp.” He tells himself he seeks “ultimate freedom,” and sets off across the U.S. en route to Alaska, working odd jobs and meeting eccentric or otherwise illuminating characters. On a South Dakota farm, he works for Wayne (Vince Vaughn), at once exhausted and energized by the physical labor, mostly bemused by Wayne’s conventionally “outlaw” machismo.

While it’s plain that Chris has little in common with Wayne, their mutual appreciation has seeds in Chris’ complicated rejection of Walt. An antennae specialist at NASA, Walt and Billie eventually started their own consulting company and grew wealthy. These tidbits of information are offered up alongside telling emotional particulars, as the two children observe their parents in disarray: they drink and argue, the control-freaky Walt abuses an acquiescent Billie. While these scenes suggest a rather reductive “explanation” of what drives Chris out and away, they also look forward to the alternative families Chris encounters and helps to form on the road, most explicitly with “aging hippies” Rainey (Brian Dierker) and Jan (Catherine Keener), and the resigned-to-dolor widower Ron (Hal Holbrook).

The couple especially seems a model of generosity and openness. While Jan mourns the loss of a child, both she and Rainey provide Chris with the sort of support and encouragement he never found from Walt or Billie. When Chris suggests patience in dealing with Jan’s grief, Rainey goes so far as to wonder aloud if he might be “Jesus”; in another brief moment, my favorite in the film, he leans down toward a seated Jan and tells her he’ll sit with her, as long as she wants, rather than join a group for dinner: the action is lovely, the shot exquisite. Ron also sees in the young man a lost opportunity, asking if he can adopt him. As each relationship is premised on loss and yearning, Chris’ distance-by-definition, his perpetual outsider’s status, makes him appear extraordinary. Though he doesn’t exactly explicate his aspirations, Ron, Jan, and Rainey’s faces reflect admiration for his seeming “purity,” even as he urges them to find connections in relationships.

An even more radiant reflection might be found in the long and loving gazes cast on Chris by Tracy (Kristen Stewart), an aspiring singer who lives in Slab City, an RV camp in California. Chris appreciates her performances for the camp, even flirts with her briefly, but at last turns back her tender and awkwardly adolescent desire. In this moment, Chris looks suddenly mature, where he has been so young and preternaturally wise with the adults who see in him what they need. And in this moment, the film makes clear what it is that is so compelling about him—perhaps as a person but surely now, as a mythic figure who went out into the mountains and died—the very fact that Chris makes choices, informed and not, eventually irrevocable.

Because Chris chooses his journey, because he seeks unknown alternatives to the life he has been granted, the film suggests that his adventure, even if not well thought out or particularly attentive to the feelings of others (say, his long-suffering sister Carine) may be worthy. At the same time, Into the Wild does something else, questioning not only the depressive and dysfunctional origins of Chris’ impulse, but also pondering the cultural investment in adventure and individualism, the search for “self” that can never end.

This is what makes Into the Wild Sean Penn’s great project (thus far). After the deeply internalized sorrow, longing, and rage examined in The Indian Runner, The Crossing Guard, and The Pledge, Into the Wild find another way to explore identity and damage, and to make them immediate and more abstract. The movie’s frequently stunning compositions (shot by Penn and Eric Gautier) reveal not only Chris’ ruminations as he appears framed by windows on his bus, hiking through magnificent forests or kayaking a rambunctious river to Mexico—but also his inability to immerse himself in the wilderness he cherishes and respects. Into the Wild reveals the sense of loss that drives Chris. It also shows that it isn’t only his.