Imagine Billie Holiday leaving Depression-era America behind, following Josephine Baker to Paris. Such an aural image is easy to grasp when listening to "J'ai Deux Amours" from Madeleine Peyroux's 2004 breakthrough release Careless Love.

Born in Athens, Ga., in 1974, Peyroux spent her early childhood in Brooklyn and then Southern California, before moving to the City of Lights with her mom after her parents divorced. As a teen, Peyroux hung out with the street musicians in the Latin Quarter. By age 15, she was busking with her friends, passing the hat for the Riverboat Shufflers and singing with the Lost Wandering Blues and Jazz Band. For two years she toured throughout Europe, performing the songs of Fats Waller, Bessie Smith and Ella Fitzgerald.

Signed to Atlantic Records in 1996, Peyroux returned to New York to record her first disc, Dreamland. As Lady Day was surrounded by Teddy Wilson and the rest of the Benny Goodman band for her first recording sessions, Peyroux, too was teamed with the best players in town. Cyrus Chestnut, Vernon Reid, Regina Carter and longtime Tom Waits sideman Marc Ribot all contributed to her debut. With covers of tunes by Patsy Cline, Hank Williams and, of course, Billie, Dreamland was a critical success. It sold pretty well, 200,000 copies, and soon Peyroux was touring the States, including a stint at Sarah McLachlan's Lilith Fair.

Heady stuff for a 22-year-old mademoiselle. Peyroux returned to Gay Paree and to playing on the street. Other than occasional club gigs and a festival or two, she stayed under the radar for several years. One rumor had her going under a surgeon's knife for work on her vocal chords; another had her disappearing for long periods of time.

Following Norah Jones' success in 2002, Rounder Records sought Peyroux out and signed her to a new deal, hooking her up with female-friendly producer Larry Klein (Joni Mitchell, Shawn Colvin). In September 2004, Careless Love was released, again to great reviews. Featuring songs by Leonard Cohen, Bob Dylan and Elliott Smith, her sophomore disc was no jinx, going on to sell over a million copies. Peyroux would never again have to pass the hat.

Now on the road to promote her latest album, Half the Perfect World, Peyroux returns to the North Bay on Saturday, Aug. 25, "with guest" for a show outdoors on the grounds of the Rodney Strong Vineyards. 11455 Old Redwood Hwy., Healdsburg. 4pm. $40–$65. 707.433.0919.

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