It's a Friday night in early September. Adrian Orange stands in the street outside Satyricon, playing a recorder. The plastic tube whistles and cracks, reminiscent of the year Orange—who sings and plays guitar, bass and drums—became obsessed with the clarinet for the sake of learning to play. Wind instruments had little part in the quiet folk music Orange made under the moniker Thanksgiving; for years, he performed alone on stage, with a guitar and his deep, lyrical voice. He's asked a friend to play the recorder in his newest musical incarnation, Adrian Orange and Her Band, for a show that starts in an hour.

Does the 21-year-old Portland native think his friend will pull through?

"Um, I don't know," says Orange, tall and lanky, wearing brown leather flip-flops. "I don't think so. I only asked him 15 minutes ago. He was noncommittal, kind of. Yeah, completely noncommittal." He stops to think, looking up and then left, at nothing in particular. "So, I'd have to say no." He smiles.

Two nights before, Orange was playing drums with his rhythmic noise outfit, the Watery Graves of Portland. He had barely given a thought to the upcoming Satyricon show, from who he'd be playing with to which songs off his 10 albums and numerous EPs—half made before he turned 18—he would play. According to Davis Hooker, the band's bass player and a regular fixture on Orange's countless and constant tours, Orange seldom decides those things more than a day ahead of time.

"He tours on an album that's not been made yet," says Hooker, 34, about the unlikely possibility that Orange will re-create live the Afro-pop album he just released on Tuesday, Sept. 11, on Olympia's K Records. He plays whatever music he is writing right now, often improvising songs on stage. Does he use a set list? "Oh, no," responds Hooker. "No, no, no."

Followers of Orange's career know to expect the unexpected. Since he started playing shows at age 11, his music has been unpredictable, from the lineup he plays with to the instruments he plays. But at the core, it has always been honest—much like the musician himself.

Orange remembers his transient lifestyle starting at 3 years old, when his parents split up. "I always lived in Portland a lot, but I grew up, like, at times, homeless, or at least on the verge of being homeless," he says about life with his mom, who now lives on a plot of land on Highway 26, between Portland and the Pacific Ocean, and works for the Department of Corrections. Together they led a bohemian lifestyle where Orange was encouraged to express himself artistically, first as a painter, then as a musician.

"I remember when I started playing, but I don't remember the first time exactly," he says. "Maybe 9 or 10?" In junior high he started a band called Menagerie with Vera Domini, now better known as the drummer for local all-girl rock outfit Swan Island. Their band is immortalized in a tile hanging at da Vinci Arts Middle School, which features Orange's painting of Marilyn Monroe. By 12, Orange became a regular (and sometimes door guy) at 17 Nautical Miles, a now-defunct all-ages club known for its DIY ethic.

By age 15, Orange had toured Europe and dropped out of Lincoln High School. He supported himself with record sales and shows, never really having a day job. His most consistent employment was washing dishes at restaurants around Portland, much like his dad, who Adrian only says "worked in the hospitality industry."

What happened over the next five years is fuzzy: He joined a tightly knit group of musicians including Hooker, his longtime friend and Watery Graves bandmate Curtis Knapp, and Phil Elverum, the Anacortes, Wash.,-based musician who performs as Mount Eerie but is best known for his work with the Microphones. He founded Marriage Records with Knapp, then quit managing the label. He washed dishes at Colosso, a bar on Northeast Broadway that Hooker claims now boasts a drink named the "Adrian Orange," and lived briefly in Olympia, Wash., with his then-girlfriend. All this while he toured and recorded albums as Thanksgiving, Orange's alter ego of quiet folk music and down-tempo guitar. Sometimes a friend like Knapp or Hooker would accompany Orange on guitar or drums, but mostly he took the stage solo. And during those seven years, the road was his home.

Elverum, who has been Orange's musical mentor for the past six years, describes those early Thanksgiving performances as risky. "It seemed liked it was gonna fall apart at any minute," says Elverum, 29.

The same could be said for the singer himself. "It's harder to be an adult making music than it is to be an 11-year-old prodigy," says Todd Patrick, 32, who owned 17 Nautical Miles and now lives in New York City, where he sees Orange on tour. "The standards are a little harsher."

Orange's own standards are changing, and not just in his musical experimentation. Much like his role in Watery Graves—where he sits behind the drum kit, banging his head to the beats—this wunderkind is shying away from the limelight and his singer-songwriter image. In early September, he moved into a house with some roommates, giving up a nonstop tour schedule. He traded in transience—he sometimes slept overnight at Marriage Records' studios—for a North Portland home.

"I've been kind of a workaholic," he admits about why he's slowing down. "It's doesn't feel slow, though. It feels fast…since I've been home." He talks about his choices the same way he writes Thanksgiving songs: as nonlinear narratives, mostly about feelings, intentionally vague on actual experiences. When he speaks, Orange avoids declarative statements, instead using phrases like, "Kind of," "I think" or "Well, maybe not exactly…."

For musicians who have played with Orange, time stands still: Each thinks the first time they saw Orange play could have been the first time he held a guitar, whether it was 1998 or 2002. Some talk about him as if he's perpetually a 15-year-old prodigy. It's a struggle to build his history when he might crumble at any moment.

That is, until earlier this year, when Elverum approached K Records owner Calvin Johnson about recording the music that Orange had been playing on his last tour. The album was green-lighted for live recording at Dub Narcotic Studios in Olympia. Although all the music was Orange's design, according to Johnson, it was Elverum who led and conducted the dozen musicians making the album. And while this project is unlike anything Orange has done before, the shift is not deliberate. "There's no vibe like, 'Here's my Afro-pop record,' says Johnson, about Orange's music. "It's an Adrian Orange record that has an influence from that."

The self-titled album is beautiful—wailing horns, classical guitars and up-tempo drums, like a well-orchestrated jam band symphony. But its success comes partially from Elverum's production and partially because Orange isn't standing alone. He has other musicians holding him up, their musical textures complementing a well-worn boy and his guitar. "I played a lot of shows where I was directing a band who had never played the songs before," says Orange. "But now I've completely lost that skill. But I'm really happy."

Orange is careful to describe his prolific songwriting as a career. "Playing music is really different from being involved in the music business," Orange says, knowing that he can always jam or play music with his friends or alone. But would he ever quit the music business—walk away, leaving this career behind? "Yeah," he says, without hesitation. "Definitely."

At Satyricon, Orange takes the stage with seven other band members. Some play instruments, like Hooker on drums; one girl sits behind Orange, tapping a lollipop with a mallet. No one plays the recorder. The songs are pure noise: Orange doesn't sing, but lets out guttural sounds and chants, seated near the drum kit, strumming his guitar. From somewhere in the club, there comes a yell: "Play Thanksgiving!" Orange obliges, abandoning the improvised song he just began, and starts over, again.

Adrian Orange and Her Band play a record release show at the Artistery at 8 pm on Friday, Sept. 21. $6. Check out for Cut of the Days from Adrian Orange this week.