Sheepishly, obligingly, Azazel Jacobs trespasses into the Manhattan apartment where he used to live. On Avenue A and 10th Street, above where the now-defunct Brownies used to showcase indie bands back when Jacobs was a postpunk postgrad, he pushes open an unlocked door and bounds up the steamy, unrenovated stairwell. He talks briefly of life here in the '90s, but is not feeling very nostalgic — just as quickly as he entered the building, he's back out and around the corner, onto something else.

Jacobs, whose new film Terri opens Friday, now lives in Los Angeles, but the director is still plainly a restless New Yorker from electric-socket-shocked 'fro to toe. And his latest proves how eager he is to grow up and away from what has defined him. “I'm not saying I'm winging it, but I'm constantly finding myself in places where I don't know if I'm gonna pull it off,” he says. “And I love it, man.”

The world of Terri, his lovely and subtly harrowing portrait of a California misfit who doesn't even try to fit in at high school, is a coast and millions of cultural miles away from Jacobs' own cool-kid boho beginnings, where he was immersed in the experimental films of dad Ken Jacobs, and at home in Manhattan's artsy Bayard Rustin High. While his last film, Momma's Man, was shot almost entirely in his parents' eccentrically cluttered Chambers Street loft, and even co-starred his parents, the new one takes place in a nondescript suburban high school and features John C. Reilly.

Though Jacobs has a more personal teenage tale to tell — something akin to Larry Clark's Kids, he warns — with Terri he's made a far rarer coming-of-age story that's neither a primal scream nor a promotion of precociousness, but rather a work of knowing, matured empathy. “You just want to scoop the kids up and say, 'It's not gonna last, it's gonna be all right.' But that would be a lie,” he says. “That's something my folks didn't ever tell me. That it's gonna be OK.”

“I had him pegged for an asshole,” Patrick deWitt tells me by telephone. Before novelist deWitt wrote the screenplay for Terri, he was wary of the transplanted downtown hipster who'd come talk to him as he tended bar at L.A.'s Three Clubs. “There was a touch of the cock-of-the-walk about him,” he recalls. Plus there's the art-punk look of him, with the kind of hair, threads and piercings that suggest a forbidding LP collection. “He dresses sort of how I did when I was 16,” chides deWitt, pegging the 38-year-old Jacobs as a Peter Pan in Clash concert tees and denim.

Jacobs eventually proved deWitt a bad judge of character.

DeWitt showed Jacobs notes for a novel that ultimately became the basis for a stand-alone script. It started from his recollections of classmates who seemed completely guileless. “They had no cynicism or animosity with other kids,” he recalls. “And of course these were the kids who were often picked on the most.”

Jacobs recalls the same, but from a different vantage. “I unfortunately see more of myself in the kids who torture Terri,” he admits, referencing characters in the film who callously pick on the big-boned protagonist's weight and wardrobe. “I had a confused idea of what it meant to be a man, what it meant to be punk.”

While Jacobs wanted to summon the spirit of teen classics like Heathers and The Breakfast Club, movies that “make strong choices and all go to unexpected places,” it was deWitt's penultimate sequence, a drunken, prescription pill–addled night to remember between Terri and two friends, that ultimately convinced Jacobs that he had to make the film. “To see it unfold in this way — I hadn't seen that in a movie before,” he says. “It was a place to go where I'd be completely on my own.”

The scene takes place in a work shed over a long Saturday night, presented in what seems like real time, with one desperately impulsive act leading to another, the downhill slope of momentum getting steeper and steeper. It's the memory of adolescence as a wild dance at the edge of disaster. “You don't know what you're going to do from one moment to the next. You're like a spaniel, and whatever catches your interest, you go toward that thing,” deWitt says. “And so often that thing is something really dangerous and bad for you.” But for Terri, the shed scene ends with a minor epiphany that looks major in adulthood's rearview.

After following stalled man-child characters in The Goodtimeskid and Momma's Man, the cool-kid director finally locates a worthy, if seemingly unlikely, hero in the awkward, hulking Terri. Still stripping away ingrained expectations of cool, of growing up with the unique dilemma of never being as hard-core, never having as much artistic integrity as his own father, he has found a kindred spirit in his adolescent opposite, a true outsider and outcast who can only live on his own terms.

Compared to the one that preceded it, each of Jacobs' films has been a less than obvious choice, complicating comparisons not only to his father's work but even to his own. “What I want is for people to see that my movies were made by the same person,” he says, “but never that they're saying the same thing.”

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