“It happened exactly like I thought it would,” says Richard Buckner with a rueful chuckle, remembering the time he spent on major label MCA Records. It was a simultaneous crash course in the music industry and human nature, he reckons, a cutthroat arena where you saw exactly how far people would go to get ahead. “You had to learn all these scams in order to not get scammed.”

Buckner recorded two albums for the label, 1997’s Devotion + Doubt and 1998’s Since, both well-received by fans and critics. They didn’t sell enough copies to merit a contract extension, though.

This was no more of a surprise to his fans than it was to him. As an itinerant singer and songwriter of enigmatic persona and ever-changing address (San Francisco, Austin, Brooklyn, Alberta…), Buckner is difficult to capture or frame, mining a seam of rich ambiguity between folk and experimental idioms in songs that are as transient as their maker. Buckner’s traditionalist streak can be too much for out-music fans, and vice versa. His albums thrive on intimacy and an inviting opacitynot exactly the stuff of penetrating marketing campaigns. What zealots love about him tend to be the things that account for his sometimes-shaky foothold within the music industry.

Thus, as if overcorrecting after aiming too high, he landed on the small but respected Chicago indie Overcoat (former home of North Carolina’s The Kingsbury Manx). Buckner was more comfortable with its business model because the transactions were clear and minimal.

“I tend to make my records on a shoestring budget,” he explains. “With a major, you’re making a $90,000 record, and you have no idea why.”

After exploring the extremes of the industryfrom the maze of a huge major to the closet of a tiny indiethe middle ground of a place like Merge made sense for Buckner. It remains small enough to be approachable, and nimble with its resources (especially important in these perilous economic times). “It’s just like I’m calling up to talk to my friends,” he says of business with Merge.

And the label’s blend of star power and connoisseurship helps talented but underexposed musicians like Buckner. That is, being associated with high-profile acts like The Arcade Fire and Camera Obscura offers an invaluable bit of credibility. “I thank Merge for that,” Buckner says, “for giving me the buoy.”

Buckner returned the favor by releasing two of his finest albums, Dents and Shells and Meadow, for Merge since 2004. Earlier this year, the label reissued three of his early albums digitally. His third new work for Merge is slated for 2010.

An institution as established as Merge also insulates Buckner from practices he finds confusing and distasteful, like self-marketing. That’s all well and good for younger musicians, for whom the processes of art making and art selling are increasingly blurred, but Buckner admits he’s of an older guard. He believes that the selling part is best left to others.

“Some people have gotten a long way in this world,” he says, “self-promoting their art, and you think, ‘That’s great, but God, how much does it suck out of the other thing?’” Buckner remembers seeing a Joe Coleman lithograph he loved years ago at a gallery in Portland. “I was talking to the rep about it, and soon the conversation wasn’t about the piece. It was about investments and the number of pressings and stuff like that. I ended up not buying the piece because I didn’t like the experience.”

Oh, and he doesn’t have any business skills. “I’ve thought about starting a label that, instead of giving advances, got a health care co-op for the musicians together, and I’ve talked to friends about it, but none of us are businesspeople,” he says, laughing. “I can barely balance my checkbook.”

And that might be the best thing about his current situation, at least for Buckner: Merge remembers that a label’s job is to do the “dirty work,” and let the artists focus on, well, art.

Brian Howe is a poet and freelance writer living in Durham. He is a longtime contributor to the Independent Weekly, Pitchfork Media and Paste.