Ani DiFranco is a singer-songwriter and political rabble-rouser who began plying her trade as a strong-willed folkie in a Buffalo, New York, bar called Nietzsche’s. She runs her own label, Righteous Babe Records, which was a model of D.I.Y. media long before major labels started doing the dinosaur. When Prince had his notorious falling out with Warner Brothers Records in the nineties, it was DiFranco’s business model he cited as an inspiration to jump ship. (And much to her amazement, they’d go on to record together.) Back then, she’d occasionally turn up on the covers of glossy magazines. But as a kinetic human, she was never too comfortable being reduced to other people’s sentences (doubtless these included). When Ms. magazine—surely a more empathetic observer than most—profiled her in their twenty-fifth-anniversary issue as primarily an entrepreneurial pioneer, she took exception in a gently corrective letter to the editor, which concluded:

Thanks for including me, Ms., really. But just promise me one thing; if I drop dead tomorrow, tell me my gravestone won’t read:

ani d.
CEO.

Please let it read:

songwriter
musicmaker
storyteller
freak.

Of late she’s kept a low media profile, touring relentlessly and internationally, filling places like Carnegie Hall, selling modest numbers of records by her and other fellow musical travelers. She remains an activist. In the days after the September 11 attacks, when songwriters were channeling empathy, she wrote (and later recorded for the live LP So Much Shouting/So Much Laughter) a long-form poem called “Self-Evident” that announced “it’s time to get our government to pull its big dick out of the sand of someone else’s desert.” Recently she devoted time and energy, alongside Willie Nelson and others, to the presidential campaign of Dennis Kucinich.

We spoke for about an hour this past winter before her concert at the Mid-Hudson Civic Center in Poughkeepsie, New York—also home of Vassar College, a progressive women’s school which provided her with her first big performance paycheck once upon a time. In a concrete-walled “green room,” barren but for a single sixteen-ounce plastic bottle of mineral water, DiFranco perched on the edge of a curveless couch. She periodically tucked her unraveling dreadlocks behind her ears while speaking; her Celtic-looking collarbone tattoo peeked from the zippered collar of her ribbed polo shirt like a necklace. Later that night, she had a thousand-plus people screaming as she recited poetry. It was an encouraging sight.

We spoke again this spring by phone while DiFranco was on tour in Anchorage, Alaska. She has a new album titled Educated Guess. On it, following a spell leading a jazz-funk band with samba tendencies, she returns to...