It's barely 1 p.m. down on New York's MacDougal Street, and Garrett Hedlund is checking out the ladies. We're in the back room of Minetta Tavern—once a grimy, neon-spangled haunt for Greenwich Village bohemians, now a buffed Keith McNally restaurant with a $26 burger anchoring the lunch menu—where, at present, the waiter is blocking Hedlund's view. Hedlund, dressed in a charcoal shawl-collar sweater and gray jeans, cranes his neck for a better angle. "Yep, they're already drinking," he says, sounding pleased, and the waiter and I follow Hedlund's gaze to four older women wearing hats who sit sipping white wine. These blue-haired ladies are all the affirmation Hedlund requires. "Grey Goose and water," he tells the waiter.

Drink orders don't usually carry metaphorical freight, but something of Hedlund's persona is suffused in this one: the id-driven wild man jonesing for a boundaryless blast of pleasure (or at least a midday vodka)—the same wild man Hedlund unleashed in his movie-stealing performance as Dean Moriarty in the film adaptation of Jack Kerouac's On the Road—tempered by the polite midwestern farm boy at Hedlund's core, by the Lutheran propriety that's an essential part of his makeup. If a clutch of septuagenarians have already uncorked the day, then where's the foul?

The 28-year-old Hedlund spent four years immersing himself in the character of Moriarty—who was based on the real-life Beat-and-hippie chieftain Neal Cassady—a spectacularly juicy role that Kerouac himself envisioned being played by Marlon Brando in his prime and that over the decades has been attached to a slew of marquee names (Dennis Hopper, Sean Penn, Brad Pitt, Colin Farrell). But with the movie finally hitting screens nationwide, Hedlund worries what his conservative Minnesota dad's going to think when he sees him giving it to Steve Buscemi from behind. To be sure, Hedlund aims for lyrical good times, poetic bliss, transcendental grit—"To say that Garrett is a free spirit," says Walter Salles, who directed On the Road, "would be an understatement"—but he also aims to please. As Sam Riley, Hedlund's costar in the film, says about him, "He's a well-brought-up lad, isn't he?" Or maybe he's just that rare creature: a hedonist with manners and a conscience.

And on this day, Garrett Hedlund is something rarer still: a young actor, as yet unrecognizable to the wine-sipping women at Table 34, poised to break into Hollywood's top ranks. "It's funny," he says, trying to put his hinge moment into perspective. "The school I went to was a little farm school in Wannaska, student body 61 or something." This was in northern Minnesota, about 25 miles from the Canadian border, where Hedlund lived with his father, a wrestling coach and farmer, after his parents divorced when he was a toddler. "There was a kid, the only black kid in our county, Dustin Byfuglien. He won the Stanley Cup a couple years back with the Blackhawks. Out of a class of 21 kids, he and I always had to be on opposite teams on everything because we were the most athletic. We could never be on the same fucking team. But it's just . . . funny. Two kids from an elementary school in Wannaska, Minnesota. Now he's won the Stanley Cup and I'm in New York getting interviewed for On the Road."

Winning the Stanley Cup requires fierce determination, of course, but a measure of luck as well: a skate accidentally bouncing the puck into the goal here, a blind whack whizzing improbably past the goalie there. It's the same in the acting game, and Hedlund has benefited from both. One stroke of good fortune was hereditary: With his blond hair and limpid, Robert Redford–blue eyes, Hedlund's got leading-man looks to spare. Yet he's not generically handsome. His face, like his personality, has undertones: a rubbery exuberance when he laughs, a hunched, almost awkwardly earnest and entirely unself-conscious intensity when he's waxing serious. "There's a vulnerability and sweetness that doesn't cross the border into there not being a masculinity about him," says Tim McGraw, whose roles alongside Hedlund in Friday Night Lights and Country Strong led to a friendship. "You can't help but fall in love with the guy."

Also in the luck department, one has to note the first acting role Hedlund snagged, at 18, after driving to Los Angeles in a beat-up Chevy S-10 pickup with purple lightning bolts on its doors and a giant case of ramen noodles in the back: opposite Brad Pitt and Peter O'Toole in the 2004 swords-and-sandals epic Troy. If it wasn't quite like Lana Turner being discovered while drinking a Coke at a Hollywood soda fountain, it wasn't all that far off, either.