Music has rules. From voice leading in Western harmony to the entry requirements for American Idol, the authorities tell us certain guidelines must be followed. Such is the way forward. Not so for Baby Dee. In her storied life, this multi-instrumentalist and songwriter has progressed erratically, backward, sideways.

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With her new album, Safe Inside the Day, she returns to square one—the Cleveland home where she grew up—while landing in a better place. Dee's sublime earlier work frequently felt rarified, gentle. Now she boldly pulls a full face-plant into her messy childhood. Blues, bawdy songs, medieval dances, and snippets of Irish airs elbow each other across the parlor. In her expressive contralto, the fiftysomething singer huffs and snarls like a cartoon pirate on "The Earlie King," a twisted nod to her father's affection for the Franz Schubert lieder "Erlkönig." With its interlaced accordion and banjo licks, "The Dance of Diminishing Possibilities" draws inspiration from the day Dee's neighbors demolished an upright piano.

But Safe is not strict autobiography. It is mythology, its grotesque subjects rooted in fantasy. Tales like the slow, spectral "Fresh Out of Candles" elevate fiction over facts. "This album is emotionally far more complex than anything I've ever done," admits Dee. "And much more easily misunderstood. But they're compelling lies—that have to be told."

Initially, Dee resisted exorcising these songs. When Matt Sweeney and Will Oldham solicited Dee for a record for Drag City, her impulse was to rework older selections. But the new songs would not stay silent. "I didn't want to bring this dark thing into the world. But Will talked me into it."

Oldham and Sweeney relieved their star of many essential responsibilities, recruiting players from Chavez, Current 93, Antony and the Johnsons, and even Andrew WK on bass. Most tough calls—"including the ones made to prevent me from doing stupid things that would've fucked it all up"—were left to her producers. Not unusual for a prefab pop icon, but for an independent artist who previously played and produced everything herself, a sharp change of tack.

Will Safe make this jocular oddball a celebrity? Unlikely. But Dee is veering closer to the mainstream. Later this spring, she plays five London dates supporting two-time UK chart topper Marc Almond. A ditty by her frequent costar, art-punk chanteuse Little Annie, currently features in a popular Levi's commercial. Longtime colleague Antony (she played harp on his 1998 debut) even won the 2005 Mercury Prize.

Dee didn't always move in such rarefied circles. An adolescent in the heyday of Hendrix and the Who, she preferred monks to the Monkees (although she admits a fondness for Johnny Cash). "My life used to be a series of obsessions, and Gregorian music was a big one." In 1972, she relocated to New York, where she remained for three decades. When her professor in conducting realized this pupil would never willingly wave a baton over anything composed after the 16th century, he urged Dee to pursue church music instead.

For the next 10 years, Dee served as musical director for a large South Bronx congregation. Initially, it seemed an ill fit—"it gave me the heebie-jeebies to picture myself as this nerdy organist"—but when she learned the choir loft loomed 40 feet over the pews, she was sold. "I adore being up high!"

Teetering in the skies is a recurring motif in Baby Dee's life; at various points, she worked climbing and felling trees, and performed on an oversized tricycle. She also drove a cab, moonlighted as a sideshow attraction... and began life as a boy. All footnotes that she frets might eclipse her musical accomplishments.

"Every once in a while, I get a review that just talks about Baby Dee as this woman who writes these songs, and completely leaves out all that baggage," she sighs. "And it feels like the dogs have stopped humping my legs and I can walk normally now."

Such respites come more frequently now, such as last December, during a gig at Joe's Pub. The backing band included not only Sweeney and Andrew WK, but also Dirty Three drummer Jim White. "Looking around the stage, there were all these guys, regular guys, and they're there for me. No big deal. They're my friends, and we're playing music. It was lovely. As a kid growing up, or even in the 1990s, when I was riding around on that tricycle, I wouldn't have imagined the world to be that serendipitous." recommended