WILLY VLAUTIN has a set of water glasses sitting on the floor of his office in St. Johns. They're from the set of The Motel Life, the 2012 film adaptation of his first novel. Kris Kristofferson used them in a scene. Vlautin jetted to Rome for the movie's premiere.

Meanwhile, Drive-By Truckers co-founder Patterson Hood has turned Pauline Hawkins—a character from Vlautin's latest novel, The Free—into a song. Fellow Portland novelists Chelsea Cain and Chuck Palahniuk recently brought Vlautin along to a big pajama party/reading in Los Angeles. That wasn't long after the scholarly critic Robert Christgau reckoned that Vlautin is "an important and arguably major American novelist."

These are all good things. Great things. Cool as hell things. It'd be hard to find anyone in Portland who hasn't been rooting for these kinds of things for Vlautin since he first began playing around town with his band Richmond Fontaine.

But one might wonder what all this success could do to one of the last of the pre-Portlandia Puddletown sad sacks.

Well, he isn't writing comedy.

"I did write my version of 'Fancy,'" he says. He's sitting with Amy Boone, the singer for his new band, the Delines.

"Am I a prostitute in it?" Amy Boone asks, laughing.

Probably—given that "Fancy" is a 1969 Bobbie Gentry song about an 18-year-old whose mother points her to just that profession as a way out of poverty. The good news in the exchange is that the two are already thinking about their second album together.

Colfax, the Delines' debut, is the best kind of country soul music. It's Gentry and Dusty Springfield. It's lit by the backside of the neon and all the broken hearts and dreams that get swept up at 3 am as the chairs go up on the bar tables.

"I like people who are in the fight, that have a dent or two in them," Vlautin says. "They're wounded, but they're not going to take a lot of shit." That's true in his novels, too. And that's true with Richmond Fontaine's records. But this time, thanks to Boone, Vlautin was thinking more about tough women than down, out, and dangerous men.

Boone is the singer and main songwriter for the Austin band the Damnations. Her sister, Deborah Kelly, handled the female vocals on Richmond Fontaine's last record, a concept piece called The High Country. When Kelly couldn't tour because she was pregnant, Boone stepped up. By the time the tour was over, both she and Vlautin had plans.

"I wanted you to write more duets," Boone says.

"I wanted to write you a record," Vlautin says.

So he did. They recorded it with the Decemberists' Jenny Conlee-Drizos on keyboards, Tucker Jackson on pedal steel, Freddy Trujillo on bass, and Richmond Fontaine's Sean Oldham on drums.

Vlautin dug it because he didn't have to sing. Boone liked not having to write, and having the chance to climb into Vlautin's characters—women who do what they have to, and some who can't quite. Wounded,but working.

Boone loved the songs as soon as she heard them. "I guess I know how to sing sad," she says. Vlautin writes to her strength. But, as with much of his work these days, redemption throws the last punch. "The sun is coming up," Boone sings on "82nd Street," which closes Colfax. "I ain't done in."

If Vlautin's figured out any meaning of success in recent years, it's contained in those lines right there.