A stranger plops down. He has a question for Randy Bickford. “What band are you in?”

“The Strugglers.”

“Is it a struggle?” There it is: the easy band name pun, the eternal and always available spin on the tag some well-meaning project has chosen. But, then there’s the question: Well, is it?

In Chapel Hill, and especially here at Orange County Social Club in Carrboro, it’s an inquiry beyond rhetorical. Around here, some estimates hold that there’s one band per capita. Bickford’s violinist, Daniel Hart, plays with four bands on a regular basis. He’ll sit in with most anyone who asks.

“We struggle, indeed. We struggle against that joke, too,” Bickford smiles, frustrated by the fact, if not by the joke.

Bickford’s case, though, is a bit different. This isn’t his hobby. His work–writing songs and singing them in a magnificent parched and cracking baritone, comparable to Will Oldham or David Berman, maybe Eddie Vedder–is just that: work, an all-consuming task. He arranges almost all of the instrumental parts on all of his albums, and his live shows are slow and directed, building behind the weight of a writer worth his words.

“If you look at the lyrics in my songs now, it’s very painstaking, I think. Every line is very carefully constructed, and that comes from a long, slow process of sculpting or honing or whatever with my craft,” says Bickford, who wrote his first song at 10, trying to imitate his hair rock idols.

What’s more, Bickford, 27, is good at the struggle. His latest, You Win, is a high accomplishment, an immaculate and austere album by a songwriter coming into his own by giving the most gorgeous songs of his career–the ponderous epic “You Win,” the aching “Necrophilia,” the strident “Racing Down One Path”–to the most capable outfit–violin, piano, guitar, bass and a drumkit–he’s ever worked with. Chris Eubank added cello parts “that I didn’t know were possible,” and Bellafea’s Heather McEntire, voice soaked sweetly in reverb, became the first Strugglers guest.

But the struggle is a complex, befuddling thing: Acuarela Discos, the Spanish label whose roster reads like some well-studied college student’s favorite band list, put out his last EP, The Fair Store, and released You Win on Oct. 18. Two Acuarela bands–The Clientele and Destroyer–are signed to local indie label Merge, and Acuarela acts like Xiu Xiu, Tarentel and The Decemberists have all found homes with some of America’s most respected labels.

But Bickford has had no such luck in America. You Win, recorded in Mebane with Jerry Kee, will be imported back into the country through Acuarela’s stateside distributor, Darla, a California label and wholesaler. It’s an absurd notion, and Bickford–who has toured Spain with Destroyer and Frog Eyes, a Canadian band with an American deal–has to cope.

“It’s a combination of bad luck and not knowing the right people,” says Bickford, who moved back south to Chapel Hill after moving from his native Virginia to New York. “Unless I’m really out of touch with reality, when this record comes out, there will be sufficient interest from some American label. But who knows?”

Portions of You Win are unintentional metaphors for Bickford’s career and outlook: His elliptical characters are burdened with the weight of a grim world, but they press on, persevering in the face of severe stagnation and disappointment. They’re bound to a hard-sell hope and a hard-lost reluctance to be done. They don’t quit.

Three albums and an EP into it, Bickford wants this to work, and he has committed. But he knows he can’t wait forever.

“If this album doesn’t ‘make all my dreams come true’ or whatnot, I’m going to make another one and try and make the best one I can make. But I will be a little less–well, I’ll always make music–but, right now, I’m completely throwing myself to it,” says Bickford. “If it doesn’t work, it will cease to be the main thing. I don’t want to be trying to find that big break when I’m 33.”

For now, Bickford is going for it. Acuarela hired a New York publicist to ensure that You Win reaches the right press outlets. They hope that positive exposure will cause an American label either to re-release You Win or help him with the next one. But even that can be frustrating: A month before You Win was released, press advances began to surface for sale at amazon.com.

It’s a struggle all right, but Bickford–“blessed persistence”–is ready and waiting. Until it happens, he’ll be here, plugging away with that resonating chorus from the album’s brilliant second track: “I am racing down one path/Fast as I ever have.”

The Strugglers play at Local 506 Friday, Oct. 21. Schooner and Heather McEntire of Bellafea open.