Bon Iver plays with The Rosebuds Friday, July 29, at Raleigh Amphitheater. Tickets for the 7:30 p.m. show cost $36.50–$52.50.

It’s nearly 4 a.m. in the Milwaukee casino Potawatomi, and the roulette wheel isn’t cooperating. Justin Vernon, the lead singer of the band Bon Iver, is in his second stack of chips totaling $200, and this set, played with smooth teal tokens, appears to be going no better than the last. The ball tumbles and pauses just past his chosen numbers, often skipping his splits entirely.

The dark-headed, uniformed man controlling the table is polite but also diligent. He appears permanently slumped from staring at the wheel and the board day and night, like a Lamarckian cave dweller whose body has bent to its function. When the ball stops, he calls out the winning number, looks at the board and takes the losing bets into his possession.

The slot machines and video games fill the room with a near-psychotropic hum. Cigarette smoke moves in great, unseen clouds. When Vernon asks for a Budweiser, a cocktail waitress says that they’re done serving beer for tonight and instead offers him a Pepsi in a paper cup. He doesn’t protest like a celebrity might, or tell her the truththat, by proclamation of the Mayor of Milwaukee, today is Bon Iver Day in the city. That he’s just sold out the first show of one of the summer’s biggest tours a mile away and that he’ll do the same tomorrow night. That he just debuted a nine-piece band as sharp as any outfit in the country, that he sold more than 100,000 records of his second album in only one week last month, that he’s friends with Kanye West, and that (Brett Favre and Scott Walker possibly excepted) he’s probably Wisconsin’s most recognizable celebrity.

Rather, wearing a black Bon Iver shirt, red chino shorts and a dirty blonde beard that juts abruptly from his jawline, Vernon, now 30, looks just like any other post-grad looking for late-night fun. He just scratches his head and grabs a Pepsi as the man with the slumped shoulders calls out another wrong number. Vernon’s stack is disappearing.

“Oh, well,” he says, leaning heavily against the far end of the table. “I was up $800 the other night.”

Vernon’s entire party seems to be down right now. Matt McCaughan, one of Bon Iver’s two drummers, is playing for small stakes, pulling just $40 from his wallet and steering clear of the cash machine. His chips quickly disappear. Like Vernon, Darius Van Arman, who founded the record label Jagjaguwar in Virginia 15 years ago, is playing large and losing large, too. Kevin Duneman, one of Jagjaguwar’s employees, stands behind everyone else, agreeing that roulette seems like a good way to lose a lot of money very quickly.

Vernon hears Duneman’s doubt and, after asking for a few lucky numbers, offers a morsel of encouragement: “You’ve got to keep playing for a while,” he says, turning from the wheel to Duneman and back to the wheel, “and eventually something crazy might happen.”

Sure enough, it does: Van Arman is the first to have luck with the once-unmerciful wheel. He lands a series of successes21, 22, 3 and 14, in particularand Vernon starts following his lead. The bank rebuilds. Every few turns, the man with the slouched shoulders asks his boss to exchange a stack of 50 chips for a $100 piece, so that Van Arman and Vernon’s piles don’t spill over the sides of the table. Van Arman hands some chips to Duneman, who now obliges the invitation to join at no risk. He soon pays Van Arman back and starts making his own money.

It’s now nearly 4:30 a.m. Everyone is sitting instead of standing. But high fives and smiles are abundant; they are finally winning.

Less than five years ago, Vernon wasn’t really winning at all. He was living in Raleigh, in a little duplex off Wade Avenue that sat in a wooded lot along Fairall Drive. His college band, DeYarmond Edison, had moved from their hometown of Eau Claire, Wis., to Raleigh in August 2005, looking for a change of pace that would spur their creativity. In Eau Claire, they were hometown heroes, a band of brothers and best friends who played (as Vernon put it the first time I ever interviewed him, in 2005) rock with “a certain kind of tenderness.”

They did well in the Midwest, but they wanted to test their songs for new audiences with different expectations. They visited the Triangle once and later found a house on Craigslist. That summer, eight of themfour band members, three girlfriends and an old pal named Keil Jansenmade the move to a big white house at 2209 Everett Ave., across from the city’s first shopping center, Cameron Village.

In Raleigh, DeYarmond Edison feverishly evolved. Not only had the band started to cultivate an allegiant local following, but they were also pushing their artistic limits well beyond the earnest folk-rock of Silent Signs, the album they had made just before moving south. Shows suddenly incorporated growling, textured drones and extreme dynamics in volume. During a very quiet passage at an early show at Raleigh’s Kings Barcade, a bartender actually turned on the house music, thinking the set had ended; the band asked that he turn it off, and continued playing.

A month later, DeYarmond Edison began a four-show residency at the multimedia space Bickett Gallery. Their stated goal was to expand the reach and techniques of the band by assigning each member an area of expertise to research. They would then develop a repertoire based on what each member had learned. Drummer Joe Westerlund explored free improvisation, while keyboardist Phil Cook mined early American string band music that DeYarmond Edison could reinterpret. His younger brother, Brad Cook, started writing homages to experimental 20th-century composers, while Vernon made a simple request: Everyone in the band should just sing, without reservations. For the first time, he even tried to use a voice that wasn’t his comfortable, rustic baritone. In a haunted falsetto that was as uncertain as it was beautiful, he delivered Mahalia Jackson’s version of the spiritual “A Satisfied Mind.”

In retrospect, the residency pushed the band to the breaking point, exposing the dichotomies within the members’ respective musical tastes too much to remain functional. Vernon soon recorded a solo EP, Hazeltons, releasing it by himself in an edition of 100 homemade CD-Rs.

One subsequent Sunday afternoon, the band was rehearsing at Vernon’s house on Fairall. He’d been sickfeverish, tired and a little grouchy, symptoms one doctor thought might be Lyme disease. During a group improvisation, Brad Cook, his best friend since they’d met in summer camp as kids, noticed that Vernon didn’t seem to care, that he seemed to be checking out. Vernon couldn’t deny it.

“The Bickett residency, ironically, was the most I’ve ever learned about music and simultaneously the reason we started to break apart. We realized there were so many things we’d never explored as musicians,” Vernon told me earlier this year. “I had this intense friendship with all these guys, and it was like we had gotten divorced. We made all these life commitments to each other. I couldn’t imagine going through something deeper.”

But DeYarmond Edison’s dissolution wasn’t Vernon’s only problem in Raleigh. Rather than Lyme disease, he suffered from mononucleosis of the liver. He had given up his job at the restaurant The Rockford, so he was broke, too. He wasn’t speaking to his best friends and bandmates of the last decade, and he had just broken up with his girlfriend, Christy Smith, who remained his roommate in the duplex. He wrote songs that were fueled by the break-up, including Bon Iver’s hallmark “Skinny Love,” and played them for Smith in the duplex. It was, as they both remember, awkward if bittersweet.

Vernon had never really loved North Carolina, something he confessed every time he returned from a DeYarmond Edison tour in the Midwest. But now he had a gambling problem and no money, some songs and no band. He was ready to go back to Wisconsin. As a press release posted on DeYarmond Edison’s MySpace page said, “Justin will temporarily/ indefinitely be heading back west, recording and performing as himself. I am sure there will be new recordings from him in no time.”

Before Vernon could leave, Ivan Howard of The Rosebuds introduced himself at the first show by Megafaun, the trio that the Cooks and Westerlund formed immediately after DeYarmond Edison broke up. Howard knew that Vernon had recorded bands for years, and he also knew that The Rosebuds’ third album, Night of the Furies, was at a standstill after two producers. They needed help. Vernon spent the next two months in and out of The Rosebuds’ small brick home across town, helping them to finish the album not just as a producer but as a collaborative band member. Suddenly, he had a new outlet. The Rosebuds’ Kelly Crisp remembers it as a sort of artistic live-in, where everyone in the house would do everything together, from eating crepes to watching Freaks and Geeks. When someone had an idea, he or she would just head to the next room.

“It was a really inspiring time for us, and the record we were making felt maybe secondary to how much fun we were having together,” she says. “Whatever the spirit of creativity was, it was so strong that I don’t think it left him when he left us for Wisconsin. It didn’t leave us, at least.”

Echoes Howard: “A lot of our music isn’t based on theories or chords. It’s based on a feeling. I think maybe that rubbed off [on Justin].”

Vernon finally retreated to northern Wisconsin at the start of the winter. He lived alone in his family’s cabin in the woods, a tale that’s basically become folklore. He worked some on the property, clearing brush and piling lumber, but mostly he just recorded the sound of his spiritual and mental escape. Many of these songs had been written in Raleigh, but the performances were raw, unflinching, urgent examinations from someone who had a lot of reckoning to do.

“re: Stacks” was a reference to his gambling, while the bulk of the songs talked about his breakup with Smith and his old Wisconsin girlfriend, Sara Emma Jensen. DeYarmond Edison had been shifting toward more cerebral territory that, years later, came to the fore on Megafaun’s first two albums. But these performances, as Pitchfork scribe Stephen M. Deusner later noted, were all “emotional exorcism,” sung in that brittle falsetto he’d first tried at Bickett Gallery.

Within a year of Vernon’s departure from Raleigh, The New York Times, Pitchfork and innumerable music blogs had heaped praise on what he eventually called For Emma, Forever Ago. Booking agents, managers, record labels, publishers and lawyers were flying to Eau Claire, sending him contracts, asking for his attention. He kept playing for a while; finally, he looked to be winning.

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“Holocene” is the most poignant song on Bon Iver, Bon Iver, the album Vernon released via Jagjaguwar last month. A web of acoustic guitars, vibraphone and steel guitar, all layered with Vernon’s most delicate singing to date, the song is an elliptical story of redemption. The guitar part is actually borrowed, at least in part, from “Hazelton,” the title track to the EP Vernon self-released in Raleigh just before DeYarmond Edison disbanded. The song begins with an episode of blackout drunkenness in Milwaukee and moves to memories of celebrations in an Eau Claire house, where friends, including the Cook brothers, once lived. The twisting tune ends with Vernon, at home during Christmas, smoking pot with his younger brother, Nate. Together, they watch the smoke spiral into space.

“The first verse is this weird amalgamation of the darkness that came with those times,” Vernon said. “The last verse is about all of that stuff getting released.”

Tonight in Milwaukee, “Holocene” comes early in the show; the band moves with remarkable grace for its live debut, the horns and guitars sighing perfectly beneath the circular acoustic. When Vernon sings “You’re in Milwaukee, off your feet,” the capacity crowd of 2,500 erupts, ignoring the tragedy inherent in the line.

Ivan Howard stands about 10 feet from the stage entrance, beaming like an overjoyed parent for Vernon’s new band. Just 90 minutes earlier, Vernon stood in the same spot, pumping his fist and mouthing along to “The Woods,” the best song on the new album by The Rosebuds, Loud Planes Fly Low. It’s the first record by The Rosebuds that hasn’t involved Vernon since 2005’s Birds Make Good Neighbors. What’s more, this is the first time Howard has seen Bon Iver play since an early incarnation performed at Local 506 Feb. 18, 2008, the day Jagjaguwar released For Emma, Forever Ago.

“I wasn’t shocked, because I know what Justin is as a frontman, and I wasn’t shocked at people’s reactions to it, because I know how people react at shows,” says Howard of the Milwaukee debut. “But I was so proud of these soundsthe way it came together, the bigness. It was really moving. It was perfect.”

The Rosebuds have always been a revolving door of temporary memberships, arrivals and departures, but the span between Vernon’s tenure with the band in early 2007 and his reconnection with them in Milwaukee last week was one of the most difficult. Vernon joined The Rosebuds just as Crisp and Howard finally admitted that there was a problem in their relationship, and that the current configurationas husband, wife and bandmatescouldn’t last much longer. They suppressed those feelings during the tour for Night of the Furies, when Vernon played lead guitar by night and mixed his own record in the back of the van by day.

By the time they recorded their fourth album, Howard and Crisp were separated, but they chose to continue publicly as a “couple’s act,” for fear the change would impact their image. As a result, the three years between Life Like and Loud Planes Fly Low were perhaps the most frustrating for the two, as they tried to sort out their new lives only behind closed doors. When they finally broached the topic of the divorce by writing these most recent songs, says Crisp, it served as therapy, a release of tension that let them work together well once again. It’s also the best work they’ve done in six years.

In that sense, it’s not unlike For Emma, Forever Ago, a therapeutic project for a self-exiled songwriter. “I felt very un-special. So when I made For Emma, Forever Ago, I was very much making a record that I needed to make. It was my last chance. I remember coming back from living with Ivan and Kelly and staying with you, and being so much happier as a person than I was six months earlier,” says Vernon, who briefly lived in my spare bedroom while he rehearsed with The Rosebuds and mixed For Emma. “It wasn’t because I thought the record was my chance to be successful; it was because the record actually meant something to me. I felt like I was actually applying myself.”

In part to honor the inspiration they gave him and in part because he says they make “some of the most important music in the world,” Vernon asked The Rosebuds to open the first 12 dates of this behemoth tour. These shows are an arrival for both parties, the other side of a difficult and arduous narrative arc for everyone involved.

“He told me, ‘They took me on my first real tour, so I want to take them out,’” remembers Bon Iver’s booking agent, Adam Voith, sitting by the backstage door on a set of steps that overlooks the river. Tonight’s show has been in the works for the better part of two years, he says, and he’s stunned it’s finally about to happen. “One of the most amazing things about this band is it hasn’t changed from day one. Its operations, its motivations, its measures of success, its decisionsit hasn’t changed. They haven’t made one compromise.”

Oftentimes, when large bands go on tour, their booking agent and manager accept proposals from smaller bands that are interested in opening. Voith says that almost any band in the world would have wanted to open this tour; after only four shows, it is almost entirely sold out through November, from Brooklyn and Minneapolis to Oslo and Hamburg. But Bon Iver didn’t accept submissions. Vernon knew he wanted The Rosebuds.

Throughout his popular ascension, Vernon’s mentality has focused heavily on this aspect of the pack, or the friends that supported him long before any throng at Glastonbury sang along to “Skinny Love” or before Kanye West called him to ask for samples and, eventually, collaborations. Just as he has been building his aesthetic for well over a decade, and finally releasing songs he started writing four years ago, he’s also been building and maintaining the circle of people he trusts.

When he made the first promotional appearance for Bon Iver, Bon Iver, on Late Night With Jimmy Fallon, he asked his old DeYarmond Edison bandmate and musical mentor, Phil Cook, to join on piano for a medley of Bonnie Raitt and Donnie Hathaway tunes. Some producers would have paid to record this album, one of the most hotly anticipated follow-ups in a decade. (Indeed, the day the first song, “Calgary,” was released, Bon Iver was a worldwide trending topic on Twitter.) Rather than farm out the work to someone he had never met, Vernon engineered and mixed the record with Brian Joseph, his longtime live soundman and the first cousin of the Cooks. As kids, they had shared summers on the lakes of northern Wisconsin. On this tour, the drum technician, Eric Lee, is just a friend of friends from Eau Claire who shared DeYarmond Edison’s old practice space; Vernon could’ve picked and afforded most anyone in the world.

The band itself is a motley assemblage of friends Vernon has made over the years, from Reggie Pace, the trombonist he met while collaborating with Megafaun in Durham last year, to the players he calls “my two favorite saxophonists in the whole world,” Mike Lewis and Colin Stetson.

Vernon also spent a considerable chunk of 2010 recording and touring with the smooth jazz-soul act Gayngs. That band’s debut, Relayted, is a remarkable Miles Davis-like fusion of disparate styles and unexpected ideas; it was admittedly also an excuse for Vernon to put his longtime friendthe auteur and producer Ryan Olsonin the national spotlight and to gather many of his closest pals in one tour bus. Half of DeYarmond Edison, Howard and two current members of Bon Iver were all part of Gayngs.

“It’s the most innocent thing you could ever think of,” Vernon said of Gayngs, a welcome outlet from the world of Bon Iver. “There’s a bunch of people not trying to do anything to make you impressed. They’re doing it because it’s fun.”

Vernon’s brother, Nate, remains his tour manager and business partner. Just before Vernon goes onstage in Milwaukee, he finds and hugs him. “Have a good show, brother,” the singer tells the manager, his voice fighting against the roar of the eager crowd.

Together, they plan to open a cultural center in downtown Eau Claire to pay tribute to the women’s college that once stood in the town. They’ve already purchased and refurbished an old veterinary clinic in Fall Creek, Wis., a few minutes from where they grew up. It’s now a world-class recording studio and living quarters. Bon Iver, Bon Iver was recorded there, and that’s where Vernon’s new nine-piece band rehearses. But Megafaun, Bowerbirds and dozens of other Eau Claire acts have used the space to record albums with high quality and low overhead. Vernon now lives in a small apartment in Eau Claire, but several friends stay at what’s now known as April Base, keeping the place up and modifying it as they see fit.

“I’m cool with being part of something bigger than me,” Vernon says of the ranch. “That’s what that house feels like as an opportunity.”

Shortly after leaving the casino just a few hours before dawn, Vernon logged onto his Twitter accountnot the band’s official, marketing-based social media handle, but his personal sobriquet, @blobtower, named for an attraction at the Wisconsin summer camp he attended.

“All good qualities must be sown and cultivated,” he said, quoting the Dalai Lama. “We can’t expect to change overnight from an ordinary person into one with high realizations.”

Earlier that night, Bon Iver ended their set just as the new album ends. They played “Calgary,” an unpredictable surge of phosphorescence about trying to keep love together despite the odds. Backstage, Nate Vernon rushed through the wings, singing along, doing his best to mimic the falsetto his older brother has made famous.

When the song ended, Pace slipped on his bulky black shades. To his right, C.J. “Cam” Camerieri stepped behind a Korg M1, the same synthesizer that was so crucial to Bruce Hornsby’s late-’80s hits. Lewis grabbed his saxophone and stood beside Stetson, his fellow reed player; they nodded along in sync, waiting for their parts. Vernon stepped to center stage and started singing, his vocals manipulated so as to reflect the same era of pop as the keyboards. Just before song’s end, he took a guitar solo, strings squealing above the violin and horns. Voith leaned over and asked me why no one had mentioned that the song’s major touchstone might just be the sex scene in the 1986 film Top Gun. That’s less of a joke than it may seem.

As with the soft rock of Gayngs, Vernon has actually taken some flack for “Beth/ Rest.” Some have called it ironic, while others have said it’s just not cool enough for indie rock, that the soothing sounds of Hornsby don’t belong to kids who cut their teeth on Pavement. But Vernon is an unabashed Hornsby fan (“Man, there’s not enough Hornsby in my scene,” he recently told Jimmy Fallon) and has been, he thinks, since he was a sophomore in high school. That much was was evident from his time in Raleigh leading DeYarmond Edison. This is a guy who talks about crying openly to the Indigo Girls and Joan Baez, minutes after mentioning his collaboration with Kanye West.

“I literally just don’t give a shit,” he says about those responses to “Beth/ Rest.” “I have cried when I’ve been working on that song. It’s legitimate. I know what that means, where that comes from and why you cry for music. It isn’t for ironic reasons.”

After all, it’s a reflection of two decades of loving music and wanting to make music. So, really, from here on out, all bets are off.

Correction (July 27, 2011): Two photos were miscredited.