Jolie Holland's storytelling grows in scope

Say you wandered into the Rite Spot at 17th and Mission streets sometime in 1999. There's a crowd of dot-com cubicle monkeys unwinding at the bar, and a few couples lit by candlelight at a handful of tables. In front of the beat-up piano in the corner is a pretty gal strumming an old guitar and singing, her otherworldly voice floating above the din. There's something arresting about it, her vaguely old-timey music carrying hints of Appalachia and Billie Holiday with a touch of the sing-song storytelling of modern troubadours like Tom Waits thrown in.

You'd be forgiven if you shrugged off that singer as another talented unknown in a city bursting with them. But luckily that woman was Jolie Holland, who in the years since has moved beyond performing at homey Mission dives to producing goosebump-inducing albums and touring the world.

Her first album, Catalpa, was a collection of demos recorded in her Panhandle apartment and never intended for proper release. But the sound quality didn't matter. With an emotional directness that bordered on the spooky, it became an underground hit and eventually caught the attention of Waits. He got Holland signed to his label home, Anti, and her subsequent albums — 2004's Escondida and 2006's Springtime Can Kill You — grew increasingly polished while still retaining her signature intensity.

Her new album, The Living and the Dead, is Holland's most fully produced yet, and quite possibly her best. The songs teem with the kind of characters who have made her albums such colorful walks through seldom-seen parts of the American landscape. But this time out Holland — who moved to New York City a year ago — set aside her Bay Area–based band to work with a mostly New York and Portland, Oregon–residing crew of musicians. The resulting music hurtles forward with a different momentum and sonic palette. "I couldn't make [the new album] with my old band," she explains. "I really did need a rock band to perform these songs."

With collaborators including guitarist Marc Ribot, ex-Decemberists drummer Rachel Blumberg, guitarist M. Ward, and multi-instrumentalist Shahzad Ismaily, Holland recorded a typically transporting record. The Living's "Mexico City" is a twisted Beat tale told from the perspective of Joan Vollmer Burroughs, William Burroughs' wife, who in the song is writing to Jack Kerouac. "Corrido por Buddy" is a heartbreaking ode to a dead heroin addict ("He had to look me in the eye and say my name before I knew it was him/Oh, Buddy, I wish I'd been a better friend"), while "The Future" is a breakup song that looks to the past with one eye on the future ("With my arms around you tight, my love in your heart/My lust on your shoulders, like beautiful epaulettes"). Like Holland's other albums, the disc displays delicate, twangy melancholy, but here things are more varied: ethereal cellos on "You Painted Yourself In," crunchy, Rolling Stones-ish guitar on "Your Big Hands," and gorgeous turn-of-the-20th-century Mozzani harp guitar on "Love Henry."

"I like music that has characters," Holland says, explaining her penchant for writing songs that can feel like old family photographs come to life. "I used to be annoyed by it, you know, these weird old songs from the '60s that have all these characters in them. But now that's what I want to hear."

Though far from being a pop star, Holland has an audience beyond what anyone imagined when she was pouring her heart out for a few Mission barflies. Yet there's no danger of her losing touch with what makes her music speak to so many. It's the offbeat people, she says, who inspire her. "I don't know," she guesses, "I probably just attract characters cause I'm a character myself." Which also explains why the border between Holland and her music is so seamless.