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All of which means that the line on Callahan has become predictable and, in many ways, inaccurate: He is easily corralled alongside a clique of introspective indie songwriters that includes Chan Marshall (a.k.a. Cat Power), Elliott Smith, Will Oldham, the Silver Jews, Lou Barlow, and Edith Frost. His lineage is easily traced back to such archetypes as Nick Drake--fragile, melancholy, literate, bitter. Someone whose records evoke insularity as easily as they require it. Someone whose shtick is less about acting out than acting in. Someone who, when categorized as such, can look horribly precious on paper--enough to make you long for anything a little less...self-involved.
But while Callahan's records do bear the superficial marks of his reputation, they have lately far exceeded it: moody, yes, but also increasingly expansive, increasingly accomplished, increasingly great. From inauspicious beginnings, he has emerged as a remarkably powerful songwriter, and that growth seems to have coincided with an ambition to incorporate divergent styles and baroque arrangements into his work--1997's excellent Red Apple Falls features everything from horn sections to pedal steels, and the equally accomplished Knock Knock (just in stores) even enlists a children's choir. Couple all that with his eye for lyric detail and his sense of humor--which couldn't be drier if he roasted it over a bonfire--and his caricature gives way to inviting complexities.
"The whole depressive thing--it's just something that's easy," says Callahan, sounding bored on the phone from New York. "Something that most people want to think. It makes them feel better. It's kind of a dismissal. I think there's a lot more than that going on, but it's the easiest thing to say, the easiest way for people to name me so that they can forget about it."
Unlike his music, Callahan's conversation tends to be guarded. He won't let slip many autobiographical details, and he has a tendency to counter questions with questions: "That's a little personal, isn't it?" This much is known: He was raised in the small town of Pasadena, Maryland--halfway between Baltimore and Annapolis--a folksy, rural area that seems to have been touched in spirit by the neighboring South. Not surprisingly, he characterizes his youth as solitary.
"Um," Callahan says in his characteristic deadpan, "I had a lot of time to myself, which kind of made me someone who spends a lot of time not doing something. Like if you said, 'What did you do today?' I might not have an answer, but it made me ruminate. It made me a ruminator." And then, as if worried that he might be playing into stereotype, he adds: "I watched a lot of TV." To hear him tell it, his other major cultural touchstones included To Kill a Mockingbird (the first book he ever read all the way through; he was 18) and KISS--"for a month or something," he shrugs. "I went through all the usual phases." Callahan tried writing songs at 16, but waited for four years to record anything, debuting when he was 20 with the 1988 cassette Macrame Gunplay.
He moved around some after his days in Pasadena, California: to Sacramento ("I'm trying to forget it") and to a small South Carolina town called Prosperity ("Ironically, it was a town of 1,000"). He continued to record all the while, releasing a string of no-fi cassettes that evinced smarts, ambition, and perhaps a bit too much forced obscurity--of sound quality, of content, of ability. 1993's Julius Caesar was his first breakthrough; that was the record on which Callahan truly began the move from style to substance, writing good songs he wasn't afraid to hide. Two years later, Wild Love was another leap forward; not only was the songwriting ever focused and the production ever clear, but he began to experiment successfully--"Goldfish Bowl," for instance, sounds less like bedroom brooding than Anglo synth-pop. His irony and bile also began to peak: "Every girl I've ever loved / Has wanted to be hit / Every girl I've ever loved / Has left me / Because I wouldn't do it," he sang, perhaps helping explain (one way or the other) why relationships never quite work out in his songs.
The Doctor Came at Dawn (1996) probably represents Callahan's most severe soundtrack of personal desperation. Spare and bitter, its songs conjure closed scenes that hum and bleed with intense sensory details. On "All Your Women Things," the album's most piercing song, Callahan completes a surreal inventory of a 7-year-old romance's detritus: