Jon Krakauer’s bestseller “Into the Wild” chronicled the real-life, way-off-grid adventures of Christopher McCandless, a middle-class college grad whose quest for “ultimate freedom” ended in 1992 with starvation in the Alaskan wilderness. It seemed natural, if challenging, screen material — and in his fourth and by far best feature turn behind the camera, Sean Penn delivers a compelling, ambitious work that will satisfy most admirers of the book. Early-fall prestige entry’s wider prospects will depend on careful momentum building from reviews and word of mouth, with repeat young-adult biz likely if it doesn’t get pushed off screens too soon.

In some ways, adapter-director Penn has made a lyrical youth-rebellion flick in the classic late ’60s/early ’70s mode, or at least something that will be interpreted as such by viewers who’ll buy the ecstatic aspects of McCandless’ odyssey. Others may find the character, portrayed by Emile Hirsch, annoyingly over-endowed with undergraduate self-righteousness, borrowed ideals and resentment toward (who else but) mom and dad.

Penn’s precise view of him is ambiguous. With its slow-mo scenic rhapsodies, the film does seem a bit less questioning of its protag’s motives and wisdom than Krakauer’s book. But both tome and pic tell a fascinating tale, with room for myriad personal interpretations.

After graduating from Emory U. in 1990, 22-year-old Virginian McCandless felt he’d completed his duty to the parents (Marcia Gay Harden and William Hurt) whose expectations he’d often chafed against, and left Atlanta without telling them or even sibling Carine (Jena Malone). They soon discovered he’d given away his entire remaining educational fund of $24,000 (slated for law school) to charity; his car was later found abandoned in the Arizona desert. The McCandlesses notified law enforcement around the country and hired a private detective.

But Christopher, now calling himself “Alexander Supertramp,” didn’t want to be found. He stayed on the move,living off the land and pickup jobs, pursuing a romantic freedom fueled by the writings of Tolstoy, Thoreau and Jack London. His goal was to live in complete isolation in the Yukon — a “great Alaskan adventure” that proved thrilling but ultimately tragic.

Penn cuts throughout among the protag’s solo Alaskan months, brief glimpses of his formative years and vignettes from the time spent tramping in between. These vignettes emphasize significant if passing friendships made on the road: a middle-aged hippie couple (Catherine Keener and Brian Dierker) who take a parental interest; a genial, hard-drinking South Dakota farmer (Vince Vaughn); a flirtatious girl (Kristen Stewart) living in a SoCal countercultural community; and finally, a retired Army man and widower (Hal Holbrook) who comes to think of this tumbleweed as the grandson he never had.

There are also less pleasant interludes, from a few bleak hours being down and out in L.A. to a violent removal from a freight train. But greater perils await in Alaska, where all his survival skills are put to the test — and, finally, can’t win over merciless Mother Nature.

The book drew on many voices to piece together the story. At first, Penn deploys too many tactics in an attempt at a similar effect: There’s Carine’s voiceover narration, spoken excerpts from the subject’s often pretentiously self-aggrandizing journals, onscreen text and section titles (“Chapter 3: Manhood”). But eventually, they all work together well enough.

Likewise, the lengthy pic never feels overlong despite repetitious moments here and there (a few too many lyrical montages, occasionally over-indulged actor riffing). But the excessively mannered touches that flawed Penn’s prior, features (“The Indian Runner,” “The Crossing Guard,” “The Pledge”) are mostly MIA. “Wild’s” style and substance feel more organically linked; pic also has more room for humor and warmth.

“Into the Wild” feels heavily influenced by Terrence Malick, for whom Penn acted in “The Thin Red Line.” While this pic’s poetic flights may not be up to that film’s masterful level, it is certainly more satisfying than “The New World.”

Hirsch, who’s shown impressive range in various TV and lesser-seen film projects (“The Mudge Boy,” “Lords of Dogtown”), easily holds the screen in this demanding role. If his McCandless comes off as a bit blank-slate, that’s appropriate for a man-boy whose unshakable convictions are mostly of the kind that grow more malleable with age and experience.

Keener, Dierker, Vaughn and Holbrook etch memorable characters. Harden and Hurt aren’t given enough screen time (or much dialogue) to clarify whether their son judged them rashly or justly as hypocrites. It’s unclear whether Stewart means to be playing hippie-chick Tracy as vapid, or whether it just comes off that way.

Shot in a great many U.S. locations tracing the subject’s actual travels, the physically impressive production is highlighted by Eric Gautier’s widescreen lensing and an original score of acoustic alt-rock Americana, with new songs by Eddie Vedder generally fitting in well.

Into the Wild

  • Production: A Paramount Vantage release, presented with River Road Entertainment, of a Square One CIH, Linson Film production. Produced by Sean Penn, Art Linson, William Pohlad. Executive producers, David Blocker, John J. Kelly, Frank Hildebrand. Directed, written by Sean Penn, based on the nonfiction book by Jon Krakauer.
  • Crew: Camera (color, widescreen), Eric Gautier; editor, Jay Lash Cassidy; music, Michael Brook, Kaki King, Eddie Vedder; music supervisor, John J. Kelly; original songs, Vedder; production designer, Derek R. Hill; art director, Domenic Silvestri, John Richardson; set decorator, Danielle Berman, Christopher Neely; costume designer, Mary Claire Hannan; sound, (Dolby Digital/DTS), Edward Tise; supervising sound editor/sound designer, Martin Hernandez; assistant director, David J. Webb; casting, Francine Maisier. Reviewed at AMC Metreon, San Francisco, Aug. 22, 2007. (In Telluride, Toronto film festivals.) MPAA Rating: R. Running time: 147 MIN.
  • With: Christopher McCandless - Emile Hirsch Billie McCandless - Marcia Gay Harden Walt McCandless - William Hurt Carine McCandless - Jena Malone Jan Burres - Catherine Keener Rainey - Brian Dierker Wayne Westerberger - Vince Vaughn Kevin - Zach Galifianakis Tracy - Kristen Stewart Ron Franz - Hal Holbrook