WILL OLDHAM, WHO RECORDS under the moniker Bonnie "Prince" Billy, is no stranger to Portland. He played Kurt in director Kelly Reichardt's Old Joy, which adapted Jonathan Raymond's Portland-centric novella for the screen, and was shot in and around the city. Now he's returning for his encore performance: a three-night residency at the Mission Theater. When, via email, I asked Oldham to tell me about his impressions of the city, he told me just what Portland's "good" for.

"Portland was good for bikes, good for books and records, good for food, and skies," he explained. "I hear it is good for drugs, too, but my cravings seem to fall between the cracks of what is readily available." And, finally, he lamented, "Missed the zoo, to my chagrin."

Imagining a childlike Oldham giddily eyeing the elephants or wigging out in the reptile house is more than a little humorous, considering his songs are often so fragile and ghostly that you might think he was striving for the musical equivalent of a death rattle. Since the release of his haunting I See a Darkness in 1999, Oldham and his understated odes to loneliness have become something of an institution in indierock. The strange thing, though, is how he's done it. Over the course of seven years, he has built a catalog (his newest, The Letting Go, was released on Drag City earlier this year) of spare, somber recordings that don't rock so much as they gently sway.

Musically, his songs are steeped in American roots traditions, from blues and folk to country western. As a lyricist, he plumbs the depths of human emotion—from abject isolation to redemptive love—with an elegant and laconic poeticism that seems to roll off his tongue. The result is deceptively simple. After all, this is a man who adapted a D.H. Lawrence poem in "The Risen Lord" from Black/Rich Music EP and, while recording The Letting Go, read such literary heavyweights as Knut Hamsun and Langston Hughes.

More than any of his previous work, The Letting Go is a cold, even elegiac album. It teems with imagery of snow, water and sky, and frosty air. Its characters are haunted by curses and bad news, sleepless nights, and troubling memories. Part of this cool tone can be attributed to two new additions. On nearly every song, Oldham is accompanied by Faun Fables' Dawn McCarthy, whose voice is clear as glass, and a string section that conjures the chilling swells that decorated Nick Drake's "River Man." Then again, the glacial feel that pervades the album might have something to do with where it was set to tape: Oldham traveled to Reykjavik to record with Valgeir Sigurdsson, whom he met through work with Björk.

"Valgeir's studio is in his native Iceland, and I figured it would be best to work in his most comfortable environment," he explained. "The bonuses were that the forbidding landscape, foreign culture, and cold dark days would force us all to turn to each other and the task at hand for warmth and reassurance."

Portland can't compare with Iceland's severe conditions, even as the city makes its slow descent into winter. With any luck, though, Oldham can take that chill out of his bones while he's here. How about that trip to the zoo?