Except for the fact that Hedlund, unlike Turner, had been begging to be discovered for most of his adolescence. After leaving Minnesota at 14 to live with his mother in Scottsdale, Arizona, Hedlund set his sights on an acting career. At the time, he wasn't sure what that meant—"I would call talent agencies to ask what kinds of food actors ate," he recalls. By 16, he finally persuaded a manager to sign him, and he was flying back and forth to L.A., solo, for auditions, funding his airfare by working as a busboy. "All my tips went to Southwest Airlines," he says. Twenty-five flights, twenty-five auditions—and zero roles. "After my first audition," he says, "the casting director told my manager I sucked pond water."

And then, at some point—maybe the 12th futile audition, maybe the 23rd—Hedlund came to a realization. "I looked around the room, and everyone, including me, looked alike," he says. He knew he had to differentiate himself from the herd of aspiring actors with teen-idol looks. But how?

• • •

"You know the Ear Inn?" Hedlund asks. "No? It's a great bar. Let's head over." We're through with lunch, with enough booze pulsing through our veins to make the teeming, sunlit city feel that much teemier and sunnier. En route, Hedlund makes a stop at Village Music World on Bleecker Street. It's a narrow little cockpit-size old-time record store, ferociously curated by its owner, Jamal Alnasr. "I love this guy," Hedlund says, finishing a cigarette before heading in. "He won't sell you an album if he doesn't think you're worthy of it." Emerging from the store for his own smoke, Alnasr greets Hedlund like an old pal, the actor filling him in on Lullaby, the film that he just finished shooting in New York. Hedlund plays the son of a cancer-stricken man about to take himself off life support. "Twenty-three days of shooting on Roosevelt Island, in the hospital there," he explains. Once inside the store, Alnasr fetches Hedlund a vinyl album that he's been seeking, Townes Van Zandt's Live at the Old Quarter, Houston, Texas, which Hedlund holds reverently. We engage in some alt-country name-checking until Hedlund checks me with an unfamiliar name: Blaze Foley, a Texas singer-songwriter who, Hedlund tells me, wrote some killer songs before he was shot in the chest in 1989.

When he fishes out his iPhone to play me his favorite Foley song, "Clay Pigeons," he discovers that its battery ran out, probably hours ago. This is as good a time as any to note how resolutely analog Garrett Hedlund is. The dead smartphone doesn't bother him a bit. He prefers his music on vinyl. He wears a wind-up wristwatch. He doesn't tweet. His e-mail address ends with "aol.com." His voluminous journals are written in longhand. By these measures, he seems laughably miscast as the lead in 2010's Tron: Legacy.

Then again, Dean Moriarty wasn't a natural fit for Hedlund, either. He's closer in spirit to Sal Paradise, Jack Kerouac's alter ego in On the Road, played by Sam Riley—more contemplative, ambiguous, a fraction more disciplined, burning with a slightly cooler flame. Moriarty is all appetite, fervent and insatiable, a manic dervish of desire: for sexual stimulation (with women and with men; in the film he pinballs from Kristen Stewart to Steve Buscemi), for intellectual stimulation (jazz, poetry, the talismanic volume of Proust he totes around), and for chemical stimulation (Benzedrine, by the lots). Playing a role like that is a risk; it would be dangerously easy to push the character straight over the top, to overinflate all that hopped-up zeal. But the risk was exponentially compounded here: On the Road is more than a classic, it's a sacred text, a generational touchstone, the Kabbalah of the open road, with Moriarty as its prophet. When, prior to shooting, Hedlund ran into Colin Farrell, who'd been considered for the role in a previous studio incarnation, Farrell said to him (and Hedlund conveys this in a wildly perfect vocal impersonation), "Man, it's so fucking brave. Doing that part takes a lot of fucking bravery, man. Like Jesus Christ." Relating this encounter, Hedlund re-creates his own intimidated gulp. "I'm like, 'That's great. He seems braver than shit, and he's telling me I'm brave for doing this part.'"

Yet Hedlund didn't come to the role cold. His history with On the Road dated back to that realization he'd had, as a 17-year-old in an audition waiting room with a bunch of identical 17-year-old actors, that he needed something more. "I decided to try to be smarter than everyone else," he says. Reading was far from his strong suit back then. "Sports or girls," he says, was more like it. Thus began the self-education of Garrett Hedlund. "After school," he recalls, "I'd hang out at the Borders bookstore until it closed." Hedlund used it like a library reading room, dog-earing the pages of whatever book he was absorbed in before sticking it back on the shelf until the following day. "That was safe," he explains. "No one was going to buy three copies of Bukowski's Tales of Ordinary Madness by the next afternoon." His literary tastes leaned toward the raw and rebellious. Besides Bukowski, there was Brave New World, 1984, and The Catcher in the Rye, whose subversiveness he understood better than most teens: "I felt I gained something that nobody else who had to read it in school got, because I realized all this stuff on my own instead of a teacher saying, 'What do you think so-and-so meant in this moment?'" Then one day at Borders he came upon another seminal text: On the Road, which Hedlund saw as an aesthetic manifesto—it churned up feelings he'd had about small-town Minnesota, when he felt everyone "just wanted to get out"—but also as a movie. Researching the novel's tangled cinematic history, Hedlund discovered that Francis Ford Coppola was, at that time, set to direct it. He sighed. He didn't stand a chance, he thought. In Hollywood's estimation, he was still sucking pond water.