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, backwards, sideways.

With her latest 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 and 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 "The Earlie King," a twisted nod to her father's affection for the Franz Schubert lieder "Erlkönig."

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. Admits Dee, "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 W.K. 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.

Dee didn't always move in such 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. 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 she was born male. 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 W.K., 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 '90s, when I was riding around on that tricycle, I wouldn't have imagined the world to be that serendipitous."