“I’m trying to run a tight ship,” Will Oldham said when he came to the door. By which he meant “Don’t be late again.” It was a Friday afternoon in Louisville, Kentucky, and Oldham was in his working house, a cozy place that would be perfect for a small family, were it not for all the musical instruments and studio equipment. It’s tucked behind some trees on a dense residential street in the Highlands, an area known for its charming shops and rising property values. (He also has a sleeping house nearby, which is just about empty.) Oldham tends to hide his thoughts behind a faint, ambiguous smile, and hides his smile behind an unpruned beard, which can make him seem like a man out of time. This impression is underscored by his excellent posture—though that may merely be evidence of a childhood spent in the theatre, learning to be conscious of his body and how it moves. The front hall was full of CDs, books, and boxes of T-shirts, and Oldham was holding a small stack of light-blue envelopes, the same shade as the cover of his most recent album. On the front of one, he had written, “Mom . . . plus siblings.” There were concert tickets inside, and they had to be delivered soon, because the concert was twenty-four hours away. It was time to go.

He walked across the street to his car, a well-worn minivan. A bumper sticker said, “When you have overpowered an enemy, show him forgiveness out of gratitude for the ability to overpower him.” (The quote comes from Ali ibn Abu Talib, the central figure in Shia Islam; Oldham got hooked on Muslim bumper stickers after seeing some in a shop in Chicago.) Louisville is his home town: lots of people there know him, and lots more people know who he is. Oldham must be one of the country’s most celebrated singer-songwriters, and if it’s a relatively small number of people doing the celebrating—well, that just shows how hard they’ve been working. He hadn’t driven more than a few blocks before a man waved him over and asked if he had a spare ticket for the concert. He did.

Oldham has been releasing records for fifteen years, though almost never under his own name. His first recordings were credited to Palace Brothers, a name inspired by John Steinbeck’s “Cannery Row”—in which the characters’ makeshift home is known as the Palace Flophouse—and by close-harmony duos such as the Louvin Brothers, who helped expand the scope of early country music, and the Everly Brothers, whose hits from half a century ago underscored the link between country music and early rock and roll. Oldham was a student of music history, clearly, but he never sounded studious. He had an eerie, strangulated voice, half wild and half broken. And he sang vivid and peculiar songs, which sometimes sounded like old standards rewritten as fever dreams or, occasionally, as inscrutable dirty jokes.

These days, he calls himself Bonnie “Prince” Billy, and his music is a little bit easier to love and a lot harder to dismiss. He has settled into character as an uncanny troubadour, singing a sort of transfigured country music, and he has become, in his own subterranean way, a canonical figure. Johnny Cash covered him, Björk has championed him (she invited him to appear on the soundtrack of “Drawing Restraint 9”), and Madonna, he suspects, has quoted him (her song “Let It Will Be” seems to borrow from his “O Let It Be,” though he says, “I’m fully prepared to accept that it’s a coincidence”). One tribute came from the indie folksinger Jeffrey Lewis, whose song “Williamsburg Will Oldham Horror” affectionately portrays Oldham as both a hero and a brute; the joke is that most indie-rock listeners already think of him that way. And a recent, unenthusiastic review in the London Independent nonetheless concluded that Oldham was “the underground artist most likely to work his way into the Rock and Roll Hall of Fame.” Although he has never signed with a major label, and has never risen higher than No. 194 on Billboard’s album chart, his concerts sell out all over the world. If he remains a spectral figure, that is no coincidence. In an online tour diary from a few years ago, he wrote, “It is more rewarding to be complicit with scarcity than excess.”

He is known, too, as a recluse and an enigma—two words that journalists often use to describe people who don’t particularly enjoy talking to journalists. He is cagey in interviews; he hates photo shoots. But he rarely goes more than a few months without some kind of record release. And in the past few years he has swum closer to the surface. He has rerecorded some of his best-loved songs with deft Nashville professionals, prettifying—or, if you like, desecrating—his own beloved back catalogue of obscurities. He has starred in a Kanye West video, alongside the comedian Zach Galifianakis. He appeared in the independent films “Junebug,” “Old Joy,” and “Wendy and Lucy,” the new Michelle Williams film (he also wrote a melody for her to hum in it). And he played a police officer in “Trapped in the Closet,” the multipart comic opera by the R. & B. singer R. Kelly, who is one of Oldham’s favorites. It’s a small part, but he looks as if he’s having fun.

Oldham’s mother, Joanne, was still living in the home where he grew up, a two-story house on a hill at the end of a leafy cul-de-sac. After delivering most of his envelopes, he went to see her, stopping at a liquor store on the way to buy some tonic water. Joanne is a soft-spoken but lively woman who seems nearly unshockable. She is an artist; she drew the image on the cover of her son’s most recent album, “Lie Down in the Light”—the one with the light-blue cover. (Her assignment: re-create “The Wrestlers,” by Gustave Courbet, but turn it into an image of Jacob wrestling the angel.) In the spirit of hospitality, she offered a warning: she said that her son wasn’t always easy to interview. The word she used was “ornery.”

“Ornery” also happens to be the title of a profile of the country-music singer Merle Haggard that was published in this magazine, in 1990. To Oldham, Haggard, like R. Kelly, is a living hero. (In this trinity the third member is Leonard Cohen.) He says that fond memories of that story, which was written by Bryan Di Salvatore, persuaded him to coöperate for this story, although not without trepidation. In Di Salvatore’s piece, Haggard is discovered in the kitchen of his tour bus, with his feet stretched out under a table, “naked except for a plaid flannel shirt and après-ski boots.” Oldham says, “That’s, like, an ideal for me. That’s such a great life.”

Oldham served drinks and talked about a recent European tour, during which he smuggled psychedelic mushrooms across a border (he hid them in his underwear) and stole a hairpin from a flamenco singer (he hid it in his beard).Soon, it was time for dinner, and after some back-and-forth Oldham and his mother decided on an upscale pub nearby. Oldham started up the minivan, which is equipped with a fearsome-looking sound system. To demonstrate its capabilities, he cranked up an old cabaret song.

“It’s Mabel Mercer, so it’s not really a test of the system,” he said.

“I remember Mabel Mercer,” Joanne said. “God.”

The concert hadn’t been Oldham’s idea; it had come from his friend Oscar Parsons, a singer and guitarist from western Virginia (on his MySpace page, he calls himself a “skinny ass billhilly”), who first befriended Oldham by offering him some homemade blueberry moonshine. Parsons wanted to know how much Oldham charged for a concert. Oldham said, “Fuck, anywhere from zero to twenty-five thousand dollars. It depends who asks.” They rented a P.A. system, and agreed that Oscar’s group—Thomas A. Minor and the Picket Line, with Oscar in the role of Thomas—would be the opening act and also Oldham’s backing band. They asked Oscar’s sister Jennifer, who lives in Los Angeles, to print the tickets on a letterpress. She made three hundred, and they quickly disappeared from Louisville shops, at ten dollars apiece.

By way of rehearsal, Oldham and the band had spent the week giving brief, unannounced performances at local bars. On Thursday night, he had called up Joe’s Palm Room, a venerable and predominantly African-American establishment, and asked, “Do y’all have music tonight?”

The answer was no.

“Do you want some?”

No.

“So if we came down there with some instruments and played some music, would you like that?”

No.

“For free?”

Eventually, the staff had consented to let Oldham and his band play, or, at any rate, consented not to stop them from playing. A few fans managed to track him down, but many of the people in the audience had no idea that they were watching one of Louisville’s most celebrated residents, and Oldham seemed proud to have won over a few skeptics. His favorite review came from a regular patron who had been moved to shout, “Sing that shit!”

W ill Oldham was born in 1970, the second of three boys; Joanne was a full-time mother, and his father, Joe, who died in 2006, was a lawyer and an amateur photographer. By the early nineteen-eighties, Oldham was getting musical tips from his older brother, Ned, who was immersed in Louisville’s fertile punk-rock scene, and he soon developed his own adventurous listening habits—he struck up a correspondence with the noisemaker and poet Lydia Lunch, after meeting her at a Sonic Youth show during a trip to New York. (He also remembers sending a “fairly elaborate” package, including a collage, to Glenn Danzig, the former leader of the horror-punk band the Misfits; he says that Danzig, in turn, sent him a package that included a rare copy of “Cough/Cool,” the band’s 1977 début single.) Despite his strong and particular musical tastes, Oldham was taken with acting—or, more accurately, he was taken with the idea of getting into character. He studied at the Walden Theatre, appeared onstage at Louisville’s acclaimed Actors Theatre, and auditioned for a role in “Matewan,” John Sayles’s film about a coal strike in the nineteen-twenties. He got the part of Danny, a prophetic boy preacher, which meant two months away from high school, living with actors (including Chris Cooper and James Earl Jones), the crew, and a tutor in West Virginia, and earning twelve hundred and fifty dollars a week, plus a per diem. When he got back to Louisville, he couldn’t figure out what to do next; with some nudging from his parents, he finished high school and applied to Brown. He lasted one semester before dropping out; he moved to Los Angeles, then to New York, tried Brown again, and finally left for good.

All the while, he remained loosely connected to Louisville’s music scene. While he was shooting “Matewan,” some of his best friends formed a band called Slint; Oldham shot the cover photograph for Slint’s 1991 album, “Spiderland,” which was recognized, belatedly, as an indie-rock classic. But he never felt the itch to start his own band. “Singing seemed more real to me than acting—and therefore didn’t seem very interesting,” he says. He had an agent, for a time, and landed a few more roles (he played the father in “Everybody’s Baby,” a TV movie about Jessica McClure, the baby who fell down a well), but he came to realize that acting wasn’t very interesting to him, either: an awful lot of it appeared to consist of fussing over lights and line readings.

He was unmoored and, sometimes, mentally fragile. “I retreated into a purely imaginary world,” he says now, remembering the time he attempted to stop speaking, in the hope of discovering a more intuitive means of communication and a more sympathetic community. He eventually found both through music, though he started writing songs only because people around him told him to. He learned his first few guitar chords about the time he went to Brown, and began experimenting with words and melodies at the insistence of Ned and the guys from Slint. He remembers a slow-breaking revelation: “I thought, O.K., music can be a construction, like a movie or like a book. It’s not a person singing about their life—someone has actually learned a craft.” He made some recordings, including “Ohio River Boat Song,” which has become one of his signatures. (It’s a Kentuckified version of a Scottish folk standard, “Loch Tay Boat Song”; instead of singing “I look towards Ben Lawers,” in reference to a Scottish mountain, he sings, “I look towards Floyds Knobs,” in reference to some hills in southern Indiana, across the river from Louisville.) Because he didn’t have a better plan, he sent out four packages: to the New York indie-rock labels Matador and Homestead (no reply); the Los Angeles upstart Interscope (a polite no); and Drag City, a quirky young label based in Chicago.

Dan Koretzky, a co-founder of Drag City, agreed to release a two-song single and then Oldham’s 1993 début album, “There Is No-One What Will Take Care of You.” Except for a few years during which he tried putting out his own albums, Oldham has worked with Drag City ever since. The album, which included a version of a song by the mysterious nineteen-twenties gospel singer Washington Phillips, got Oldham some attention, and some gigs. (He and his bandmates were offered a thousand dollars a show to be an opening act on the 1994 Lollapalooza tour; they signed up, and, he says, saw their fee raised by two hundred and fifty dollars after the death of Kurt Cobain, whose band, Nirvana, had been scheduled as the headliner.) The songs were slow, as if Oldham’s Kentucky warble were pulling the recalcitrant instruments along, and the lyrics, which were full of references to death and sin, helped encourage all sorts of fantasies about Oldham. One reviewer wondered if the album had been recorded in a barn. Oldham says that he had set out to make a swaggering blockbuster, in the tradition of the Rolling Stones’ “Sticky Fingers.” (Suffice it to say that what he made was closer in spirit to “Moonlight Mile,” that album’s ruminative finale, than to its first song, “Brown Sugar.”) He claims to have been baffled by the response. “When people were saying, ‘This sounds Southern,’ ‘This sounds country,’ ‘This sounds Appalachian,’ I was just, like, ‘What the fuck? We made a rock record!’ ”

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The idea that he is some sort of folk-art naïf, or an Ivy League dropout pretending to be some sort of folk-art naïf, long haunted and irritated him. And he spent much of the nineteen-nineties embracing and rejecting various pretenses. Oldham’s second album, “Days in the Wake,” from 1994, is a simple recording of him singing and strumming; “Viva Last Blues,” which he made with a full band and released in 1995, includes a half-heroic rock song called “Work Hard/Play Hard.” With each album, he tweaked his name: Palace Brothers became Palace, then Palace Songs, and finally Palace Music. “Arise Therefore,” a dark and tangled album from 1996, was released with no artist’s name at all, and “Joya,” which he made twice (he thought the original version sounded “unfocussed”), was simply credited to Will Oldham.

The idea, all along, was to erase the person making the music so that listeners would focus on the music itself. Of course, it didn’t work that way: with each new release came a barrage of questions about Oldham’s new name, and the evasions only added to his mystique. And so, one day in 1998, flying back from a tour of Australia, he created Bonnie “Prince” Billy, inspired equally by Bonnie Prince Charlie, the eighteenth-century pretender to the English throne, and Nat King Cole. “He’s going to sing songs that have verses, choruses, and bridges,” Oldham decided. “He’s, like, a Brill Building or Nashville songwriter.” Oldham had finally found a role that he loved. A casual listener might not have noticed the difference, but it’s not clear that Oldham has any casual listeners.

Oldham’s fans tend to be nearly as obsessed with his music as he is (a number of fan Web sites attempt to track his output, which now includes more than a hundred albums, singles, and collaborations), but he still likes the idea of being an old-fashioned artiste, humbly amusing the general public. And this new character was proof of his commitment. He says, “Bonnie ‘Prince’ Billy can be more entertaining, ideally, than Palace Brothers were or Will Oldham was.” True to form, he signalled the start of this “entertaining” era with a bleak, subdued album called “I See a Darkness,” which had a skull on the cover. The album, which appeared in 1999, wasn’t necessarily more fun than Oldham’s previous ones but it was more direct. The title song has become one of his most popular; Johnny Cash sang it, on “American III: Solitary Man,” an album from 2000 produced by Rick Rubin, who has long been an Oldham fan. It’s a solemn song, but the homely lyrics tug against the prophetic tone of the title: “Well, I hope that someday, buddy, we have peace in our lives / Together or apart, alone or with our wives.” Part of the thrill was the feeling—however illusory—that, for once, you knew exactly what Oldham was talking about.

Tickets for the concert carried a stern warning—“No Beer, Alcohol or Drugs”—and some legalese, which, it turned out, was adapted from Ticketmaster (“This ticket is a revocable license and may be taken up and admission refused for any reason”). No address was given, in order to discourage gate-crashers; ticket holders had to e-mail for directions, which led them to a small field in the southeastern exurbs of Louisville, past a “Do Not Enter” sign, and down a gravel road. The concert site was a clearing on a lake; the land belonged to the family of Brad Reinstedler, a banjo player in Oscar Parsons’s band, whose friends had named the field Funtown and elected him mayor. Weeks before the concert, on a Louisville music blog called Backseat Sandbar, one fan spread word of the lake and advised concertgoers to bring bathing suits. Reinstedler replied, “There will be no swimming due to some unfortunate circumstances.” He had purchased liability insurance for the concert, but not enough to insure swimmers.

Cars began arriving at around five in the afternoon; they were met by volunteers who checked for tickets and directed parking. One of them explained how he planned to enforce the no-alcohol policy: “If they got more beers than what I think they can handle, then I’m gon’ take a few of ’em.” This plan proved unnecessary: alcohol consumption was moderate, although some visitors talked reverently about a “waterfall” in the woods, which turned out to be a beer keg next to someone’s car. Gate-crashers were scarce. Oldham is, in his soft-spoken way, an intimidating presence, and it appeared that no one wanted to get on his bad side. “You print the rules and cross your fingers,” he said.

Even he had to admit that this was as pleasant a concert setting as could be imagined. The stage was a flatbed trailer set up in front of a log cabin; it was a breezy summer afternoon, and people brought folding chairs and beach blankets. His mother was there, with a collection of aunts and uncles. Parsons, shirtless in swimming trunks and as skinny as advertised, sang some charming, shambling mountain songs with his band, and then there was a fake marriage ceremony, in case the neighbors were watching—they had been told that the gathering was for a wedding, on the theory that this would make them less likely to call the police. Then Oldham took the stage, with Parsons and the band surrounding him. He was wearing a maroon tank top, orange-and-pink pants, blue Crocs, and a pink Boston Red Sox cap, with “cam” and “odia” scrawled on either side of the “B.”

Parsons began strumming, and Oldham leaned in to test the microphone. “Y-y-yeah,” he said. Then he clasped his hands behind his back and started singing “Easy Does It,” the first song from “Lie Down in the Light.” His singing has grown more precise over the years, and he sometimes closes one eye, pirate-like, or shakes his head, as if he were fighting to push his voice closer to the notes that he hears in his mind. Volunteers had distributed commemorative Bonnie “Prince” Billy kazoos to the first hundred or so people who showed up, and before a song called “Goat and Ram” (which begins by expounding upon the central creed of Islam: “There is no God but God / God in your body, which is mine”) he asked audience members to get out their kazoos and toot along, creating an E drone. Someone asked why there weren’t enough kazoos to go around. “We’ve actually got a complaint box up here,” he said, motioning toward his crotch. “It’s right here.” He thought for a moment. “But it’s already full.”

There was one unexpected cover: a version of “Little Boxes,” the sixties folk hit that served as the theme song of the Showtime series “Weeds,” one of Parsons’s favorites. And Oldham found ways to transform some of his own earlier songs: “Death to Everyone,” a dirge, became a high-spirited sing-along. During “A King at Night,” he smiled at band members who flubbed the occasional note, and some of the people on blankets joined him in the refrain: “This is how I start another day in my kingdom.” Bent forward, with one knee up, he looked a bit like a court jester. The sun was setting, so the Christmas lights that had been hung above the stage seemed to grow brighter with every song. He was accompanied all night by the thrum of cicadas, and the music was punctuated by an occasional splash from the lake.

Oldham has been singing a lot of duets recently, using the conventions of male-female singing—calls and responses, low declarations and high harmonies—to mimic the stylized love he sings about, which sounds more traditional than confessional. The clear-voiced singer Marty Slayton, who sometimes sings backup for George Strait, helped him nudge his old songs a little way toward the country mainstream on “Bonnie ‘Prince’ Billy Sings Greatest Palace Music,” in 2004; the first time he heard her voice over his it was “almost an erotic experience,” he says. “The Letting Go,” from 2006, was dominated by the unexpected countermelodies of Dawn McCarthy, who leads her own group, Faun Fables, which is now signed to Drag City. (He got to know her by taking her on tour, along with a then unheralded singer and harpist named Joanna Newsom.) For his latest album, he found an unlikely duet partner in Ashley Webber, a relatively unknown Canadian singer whom he met on tour. Onstage, Cheyenne Mize, a dexterous fiddler, filled in for Webber. When he called out “O lady,” she called back “O boy!”

This most recent album, “Lie Down in the Light,” sounds generous, like an invitation. “It’s O.K. to accept good fortune,” Oldham says, by way of explaining the title. But the song of the same name, which he performed at Funtown, could just as easily describe the apocalypse:

When the sun welcomes us in And the earth’s protective skin Fails and peels back, face to chin Then we start it all again__

Why do you frown? Why do you try? Why don’t you lie down in the light?

Oldham’s voice goes up on those last three words, as if he really wanted to know. And, near the end of the song, Parsons, still shirtless, broke the eerie mood with a Jew’s-harp solo. Friends hooted their approval.