The rediscovery of the extraordinary Karen Dalton is among the more welcome trends of the recent past. In the wake of yet more posthumous releases from "the Hillbilly Billie Holiday," we re-evaluate the career of a tragic genius lauded by everyone from Bob Dylan and Tim Hardin to Nick Cave and Devendra Benhart.

Often the voices that move us most are the ones most on the edge--the ones racked with pain, the ones that sound beyond hope. One such belongs to a tragic beauty who left a paltry but bewitching legacy of two albums, the second (In My Own Time) reissued for the first in 2006.

Karen Dalton was a junkie for the best part of 20 years. Photographs of her remind me of Billie Holiday with her sleepy street-addict demeanor, her far-gone indifference to the world. Her voice, too, draws inevitable comparisons with the late Billie Holiday of, say, Lady In Satin.

Born Karen Cariker on July 19, 1937, in Bonham, Texas, Dalton's mother Evelyn was Cherokee, her father Irish. Her musical roots were rural and Baptist. By the late '50s she had a son (Johnny Lee) who remained with Evelyn when his mother enrolled at the University of Kansas and later gave birth to a daughter, Abralyn (or Abbe), by English Literature professor Don Dalton. After meeting folk singer Dick Weissman in Colorado in the summer of 1960, she moved east to New York City.

One of the few images of Dalton performing, dateline February 1961, shows her singing at the Café Wha? club with Fred Neil and Bob Dylan. Seated on a stool with her eyes closed while young Bob blows harp and Freddie Neil strums a guitar, she looks like an American Juliet Greco. "My favorite singer in the place was Karen Dalton," Dylan wrote in Chronicles, Vol. 1. "She was a tall white blues singer and guitar player, funky, lanky and sultry."

One of the reasons Dalton kept her eyes closed was that she was acutely uncomfortable on a stage. An intimidatingly handsome Amazon who quickly acquired an unwanted reputation around the Village as a kind of "Hillbilly Billie Holiday," Dalton preferred singing privately, or jamming in her kitchen with friends. Nor did she care for recording, which was why Capitol Records producer Nik Venet virtually had to trick her into cutting It's So Hard To Tell Who's Going to Love You the Best (1969) at New York's Record Plant. It says much that the recordings released as Cotton-Eyed Joe (Dalton live in Boulder) and Green Rocky Road (Dalton recorded on a reel-to-reel with then-boyfriend Richard Tucker) took so long to see the light of day.

One can hear the junkie stance in Dalton's phrasing and her intonation. "She wasn't Billie Holiday," Venet told Goldmine, "but she had that phrasing Holiday had and she was a remarkable one-of-a-kind type of thing...Unfortunately, it's an acquired taste, you really have to look for the music." The voice is horn-like, elemental, free of legato and sparing of vibrato, each note a piercing straight line to the soul.

Dalton's most affecting, harrowing performances reach back to her public domain bluegrass roots. The standout track on It's So Hard… is "Ribbon Bow," the aching plaint of a poor country girl who lacks the alluring fineries of her big-city rivals. Unarguably the highlight of In My Own Time is the chilling "Katie Cruel," with Dalton accompanying herself on her banjo with only Bobby Notkoff's electric violin for company.

It's hard not to hear "Katie Cruel" as autobiographical in its narrative of a fallen woman--a woman who may have ended her life destitute on the streets of New York. (Supposedly Dalton was also the subject of the Band's basement song "Katie's Been Gone.") The sound of Dalton's voice on the track is scary, like that of some wandering bag lady. "It's endlessly mysterious," says Nick Cave, whose song "When I First Came to Town" [Henry's Dream] was directly inspired by the track. "[It's] just so fierce and kind of haunting."

In My Own Time is a far more realized record than It's So Hard to Tell Who's Going to Love You the Best, which sounds as off-the-cuff and first-take as it almost certainly was. To first-timers the voice of In My Own Time will have a certain shock value; some will even find it hard to get past the catch in the throat that starts every phrase. Certainly there's an outsider quality to the voice as it swings through songs of loss and love, starting with Dino Valenti's anxious, dread-filled "Something On Your Mind" and winding up with her old friend Richard Tucker's wistfully resigned "Are You Leaving for The Country?" It's an album that's long captivated not only Nick Cave but Lucinda Williams, Cat Power, Joanna Newsom and Devendra Banhart.

"If I was where I would be, then I'd be where I am not," Dalton sings extraordinarily on "Katie Cruel". "Here I am where I must be, where I would be I cannot..."

"I was going to say it's a fragile voice," says Cave in the album's booklet. "But of course it's not a fragile voice, because it's been smashed into a million pieces. In ‘Katie Cruel' she does embody the character absolutely. There's something that's inherent in her voice, an understanding of this kind of sorrow. She knows how to be sad."

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