For most of us, post-graduate life looks like a nine-to-five job and an apartment north of 145th street—ideally, with good plumbing. So to abandon your worldly possessions and trek into the Alaskan wilderness is, to say the least, an uncommon choice for a kid who could’ve gone the way of Harvard Law instead.

In 1990, Emory graduate Christopher McCandless changed his name to Alexander Supertramp and disappeared into the American wild, leaving $24,000 in savings and puzzled parents in his wake. Into the Wild, an adaptation of Jon Krakauer’s best-seller, chronicles McCandless’ nomadic exploits over the next two years, and like the book, attempts to understand what makes him tick.

Sean Penn’s fourth directorial effort is a valiant one, but isn’t entirely convincing. His vision for the film isn’t just lucid; it’s downright transparent. From the opening frames, we’re whisked away on a National Geographic travelogue scored by folksy guitar riffs and lyrics bemoaning the ills of society. Even Emile Hirsch’s charisma and considerable talent can’t take the edge off lines like: “If you want something in life, reach out and grab it.” or “All is not well on the hippie front.”

Ultimately, it is Penn’s admiration for McCandless that detracts from the complexity of his character. His wealthy and successful parents (an underused Marcia Gay Harden and William Hurt), become the scapegoats for his problems; the story becomes a subsequent search for new parents, in the form of the hippie Jan (Catherine Keener) and a reclusive leather-worker (Hal Holbrook). The heavy-handed Christ imagery also fails to help Penn’s cause.

At turns awkward, sentimental, and well intended, the film plays with lofty concepts but doesn’t quite know what it’s talking about. Penn invokes Byron, Thoreau and Tolstoy, and lumps abstractions like nature, happiness, and beauty together without stopping to examine the problems in its big-hearted message. The film ingenuously makes road-tripping seem like a trip to Disneyland, where everyone you meet is a kindred spirit, happy to offer you a meal.

Despite its shortcomings, Into the Wild does have its moments of charm and success. The cinematography is extraordinarily bleak and beautiful, and Hirsch’s transformation into McCandless is organic, a testament to Penn’s skill as an actor’s director. While two and a half hours of screen time is a formidable challenge for one actor, Hirsch’s handsome mug carries the film effortlessly, from his drunken ramblings with Vince Vaughn (cue the honky tonk music) to an affectionate dialogue with an apple.

Among the film’s high points (which include a trademark political dig at Bush Sr.) is the ending, which finally situates Penn’s sentimentality in a proper context. We leave the theater, if not completely convinced, at least inspired by the message of the movie. Now if only Penn would let the images, not the song lyrics, speak for him.