Quirky, pretty girls with lovely voices are a dime a dozen on MySpace these days, but Ingrid Michaelson is living proof the Web can create a bona-fide hit single. After “Grey’s Anatomy” music supervisors discovered her song, “Keep Breathing,” online and used it on last season’s finale, buzz for the singer-songwriter reached a fever pitch.

Then Old Navy e-mailed her via MySpace and asked if it could use her single, “They Way I Am,” in its Fair Isle Sweater commercial. That led to the number-one spot on Billboard’s Alternative New Artist Album charts and the number-four song overall on iTunes. Not bad for a girl from Staten Island, N.Y., who still lives at home with Mom. “I’m looking into getting my own place in Brooklyn, but it seems kind of pointless now since I’ve been on the road,” says Michaelson, 27, speaking from her cell phone “on some street in Des Moines.”

Last week she was making her way to Chicago from Los Angeles, before returning home to New York to play a sold-out show at The Knitting Factory on Friday, with another one at Bowery Ballroom on Dec. 19. But lest you think she’s now living the high life in a tricked-out tour bus, Michaelson is quick to point out, “I’m in my mom’s minivan with one bandmate, my manager and my best friend. It’s low-budget over here.”

True to her indie roots, Michaelson hasn’t changed much since she was a musical theater major at SUNY Binghamton, from which she graduated in 2001. “I wanted to be an actress, and I tried that briefly, but I felt really lost.” Until May, she had held down a string of day jobs before sales of her second self-released album, “Girls and Boys,” propelled her into a nationwide tour.

The record is full of catchy pop musings on relationships, but Michaelson says her next album will be “a little darker.” That might surprise her fans, who, because of her personable demeanor and tendency to challenge her audiences to contests (with prizes she buys herself from the 99 cent store), treat Michaelson like an old friend.

No wonder — she’s hardly aloof or overly polished. “I don’t like to glam it up,” she says. “On stage, I wear the same jeans and T-shirt and Converse I always wear, only cleaner.” Her mother cuts her long auburn hair, and her bandmates constantly reprimand her for falling asleep with her eye makeup on. But Michaelson says there’s a method to her madness: “I like morning eyes. It looks all smoky and sexy the next day. I’m actually trying to start a trend.”

This story first appeared in the November 12, 2007 issue of WWD. Subscribe Today.