The precise moment is hard to pinpoint. Perhaps it was when he started rolling with what tabloids christened a reconstituted Rat Pack, guzzling Cristal and sharing stretch Hummers with P. Diddy and Wilmer Valderrama. Or punked Justin Timberlake. Or married frickin’ Demi Moore. But somewhere along the line, you could reasonably have said to yourself, “You know what? This Ashton Kutcher kid, who’s never been in anything I give a shit about? Fuck him. Fuck him and the publicists he rode in on.”

But you didn’t. And the reason you gave him that chance, left the door of opportunity open for Kutcher to win you over, is that he is not an asshole. You could see that despite the sideways caps, puka-shell necklaces, and lame teen comedies. Kutcher himself will tell you that’s what got him this far—not being an asshole. “Anything else,” he says, “I’m going to have to earn.” We are facing each other across a round white table in the 14th-floor office of Kutcher’s production company, Katalyst Films and Television, just east of the Sunset Strip, our butts on metal-frame chairs. Kutcher is doing something he will ask me later not to write about, something he says he doesn’t want children to know he does. He shakes his head. It’s a bad habit that he started up again after a recent role called for it.

Kutcher is tall, slender, and athletic. His feet are notably small, his fingers are long, and the backs of his hands are pink. There is a red string bracelet around his wrist. He’s wearing jeans, a studded belt, a black hoodie, and red plastic sunglasses that rest on his crown. Chin and cheek stubble provides him with some much-needed gravitas.

In person his non-assholeness does not come across as affectation. It’s rooted in the cornfields of Iowa, where Kutcher grew up—first in Cedar Rapids, with his mother, Diane, his father, Larry, his older sister, Tausha, and his twin brother, Michael, and later, after his parents divorced when he was 13, in a town called Homestead, with his mother, his stepfather, and his siblings. Michael was diagnosed at birth with cerebral palsy, a condition in which the motor-control centers of the brain are damaged, usually during pregnancy or childbirth.

“I was the kid with the big Coke-bottle glasses, the hearing aid,” says Michael Kutcher, who still lives in Iowa, where he sells retirement plans. “There was a lot of teasing, a lot of the normal mean stuff.”

Ashton was Michael’s self-appointed protector. “That was a big part of my life,” Ashton recalls, “kind of looking out for my twin.”

“Think about that,” says his best friend, Jason Goldberg, copresident of Katalyst. “‘Why my brother and not me?’” He says Kutcher emanates a particular kind of warmth—that he’s like the popular kid in school who was nice to all the losers: “That’s a big strength of his, that understanding of what it’s like to be the other guy.”