Planning Her Own Holiday

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In 1996, Madeleine Peyroux was recording her first album, "Dreamland," featuring trumpeter Marcus Printup of the Lincoln Center Jazz Orchestra as a sideman. At the time, the LCJO was preparing for a concert of film music by Duke Ellington, including a number originally sung by Billie Holiday. The orchestra needed someone to sing Ms. Holiday's part, and Mr. Printup recommended Ms. Peyroux.

Although still an unknown quantity to the jazz world, the then-22-year-old singer-guitarist from Georgia so completely captured the essence of Lady Day with her rendition of "Saddest Tale" that she gave chills to all in attendance.

Yet when her album came out, and in subsequent appearances, jazz purists didn't know what to make of Ms. Peyroux: "Dreamland" had several numbers associated with Ms. Holiday and Bessie Smith, as well as signature songs of Patsy Cline ("Walkin' After Midnight") and Edith Piaf ("La Vie en Rose"), but Ms. Peyroux was decidedly not rendering these songs in a "jazzy" way—she wasn't swinging them as, say, Ella Fitzgerald would.

Fifteen years and five albums later—her latest, Standing on the Rooftop," was released Tuesday—Ms. Peyroux is still confounding expectations.

"I know there's various opinions about what a jazz vocalist should do," she said in a phone interview from her Brooklyn home. "But I think we've really lost the context of the original term, because it's been a long time. I don't know that it really matters any more."

Ms. Peyroux plays jazz clubs and festivals, and she occasionally sings jazz standards. She also still has a distinct tonal similarity to Ms. Holiday, a deep southern accent that almost gives her a genetic predisposition to sing jazz and blues. But I was reluctant to ask her about Ms. Holiday, as it's clearly a sore point. Every reviewer compares the two, and several jazz headliners who double as comics, like John Pizzarelli and Ann Hampton Callaway, have built comedy routines around the similarity of the two voices.

"I don't know how you can avoid sounding like your heroes," Ms. Peyroux said. "If I hear a really definitive version of a song Billie Holiday did, which often is the case, it's all the more difficult."

In truth, her sound is reminiscent of Lady Day's, but that's about it; she does not copy Ms. Holiday's arrangements and she does not have her remarkable sense of time. In fact, Ms. Peyroux rarely if ever sings in swingtime. Rhythmically she's more like a country or a folk singer—more K.D. Lang (with whom she recorded Joni Mitchell's classic "River") than Sarah Vaughan.

In many ways, Ms. Peyroux's blend of jazz, pop, country, blues and folk music has been a precursor of the formula that has sold millions of records for Norah Jones in the last decade, and the archetype for the generic, all-purpose voice that is inescapable these days, when almost every singer that comes over the loudspeaker at Starbucks offers some variation on the Peyroux-Jones sound.

"Rooftop," Ms. Peyroux's sixth album, includes eight original compositions and four fresh interpretations of songs by iconic authors, including John Lennon and Paul McCartney in the opener "Martha, My Dear," and Bob Dylan's "I Threw It All Away." Her treatment of Robert Johnson's hypnotic blues "Love in Vain" is so stark as to portend a coming apocalypse. She also covers the poet W.H. Auden with a new setting of "Lay Your Sleeping Head, My Love" devised by guitarist Marc Ribot.

Ms. Peyroux describes the album as "rootsier" than anything she's done before, and other than her voice—which still sounds vaguely like Lady Day—there's no attempt to replicate the sound of a traditional jazz singer. Which is a good thing: She's doing what comes naturally, even if that means, in her case, sounding like somebody else.

"Right after 'Dreamland,' it became obvious to me that it was my journey to look for my own voice in all these things, with Billie Holiday's help," she concluded. "And not without her."

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