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Read our Song of the Week interview with James Jackson Toth and Jessica Lynn Toth

If you’ve ever been a fan of a band before it was famous, the phrase “sellout” probably still makes you queasy. Maybe you weren’t down with Dylan the Electric, or maybe it was you who dismissed Sonic Youth when, in the late ’80s, the squalling New York post-punks rose through the indie ranks to sign to the major label Geffen Records. Or perhaps you disavowed Metallica when “One” broke Billboard‘s Top 40 in 1989. In each case, let’s hope not: History is stacked against you big time.

If a musical movement is worth a listen, it will probably eventually produce a star, someone thatfor varied reasons of marketing, happenstance or, dare I say, qualitywill rise above the ranks and drag its cadre near the spotlight. Because we treat bands we love like personal property, those new stars will inevitably be termed sellouts, even if the music’s unchanged or still good.

Exceptions abound, of course: Direct descendents of Darkthrone and Merzbow shouldn’t count on money spins anytime soon. Similarly, the group of American musicians collectively known for the better part of this decade as New Weird America, free-folk or freak-folk will likely never crack the Clear Channel charts, either. Outsider figurehead Devendra Banhart may date Hollywood actress Natalie Portman, and CocoRosie may have nabbed a multi-page spread in a July New York Times Magazine. But don’t expect the beloved beardos and weirdos to be on sale at Wal-Mart summarily.

That doesn’t mean these acts can’t polish their soundand subsequently be called sellouts: Just last year, Six Organs of Admittance, Sunburned Hand of the Man and Magik Markersthree figureheads in the stateside psychedelic resurgencemade their most accessible records to date. Earlier this year, guitar-driven California band Howlin Rain released Magnificent Fiend, its debut for Rick Rubin’s RCA imprint, American Recordings.

The most completely realized of these records, though, is Waiting in Vain, the first album by New York-born, Nashville-outskirts-based songwriter James Jackson Toth under his own name. While leading variations on his band Wooden Wand (& the Vanishing Voice, & the Sky High Band…) for the last decade, Toth has reportedly released 100 titles. Most of those were limited-edition CD-Rs, cassettes or wax, but across most of his immense catalog, Toth’s work was unified by literate, provocative lyrics scrambled and scattered by tape hiss, distended instrumental sections and free-wheeling improvisational flotsam. But Waiting in Vain is a straight-ahead singer-songwriter record, with country, soul and rock graces bedded beneath Toth’s stories and wisdoms and imprecations. Toth sings alternately like Al Green, Jackson Browne and Mick Jagger, backed by a careful, patient band that includes Wilco’s Nels Cline, Deerhoof’s John Dietrich and Vetiver’s Andy Cabic on guitar, and Espers’ Otto Hauser on drums. Toth comes off sounding like a pop natural.

“I’ve always written a lot of pop songs, but it just wasn’t what I was interested in doing before,” explains Toth outside of a gas station in Louisiana, already an hour late for his quintet’s arrival at a club in New Orleans. “I always shoved those songs to the back of the pile. Different experiences and different people that you meetthat changes your work, you know? I probably couldn’t have made this record five years ago, but I probably could have made something similar. I didn’t want to.”

Toth even wrote mid-album highlight “Midnight Watchman” in 1997, just before he started calling himself Wooden Wand. Indeed, despite its higher production value and clean presentation, Waiting doesn’t feel discontinuous with Wooden Wand’s previous output. Last year’s James & the Quiet showcased Toth as a settled songwriter in a serene band setting, but Waiting in Vain makes the songs stick. Lyrically, Toth still turns an empathetic gaze toward society’s fall guys, romantically defending the underdogs, especially the female ones (“Becoming Faust” and “Poison Oak”) while casting himself as dangerous (“Look in on Me”). And though the playing and arrangements follow more customary forms, they’re not stripped of personality. Toth avoids a chorus on the opener and tears hard through a verbose, Dylan-like, moving audio-picture on “Beulah the Good.”

“I listen to a lot of weird, experimental stuff, but I also listen to a lot of The Rolling Stones and The Kinks. I wanted to make something that was part of a lineage that was important to me, including punk and including jangle pop,” says Toth, 30. “I felt like I was letting influences out that I wasn’t even aware of. I’d get in studio, and our bass player would say, ‘That’s Violent Femmes!’ ‘That’s Grant Lee Buffalo!’”

With those realizations, Toth touches on a central weakness of the whole sellout argument, anyway: Fans and critics often assume that if a band is in the underground, it must be of the underground and built by the underground; that the same musician who loves obscure folk-ish records by Hapshash & the Coloured Coat or Jan Dukes De Grey hasn’t internalized, can’t respect and can’t respectfully approach less cool mainstream fare. So, naturally, when a “weird” act comes down to Earth, albeit slightly, it’s seen as an act of band betrayal and met with exclusion by the old fan.

But when Toth does his best Jagger on the slow blues of “Look in on Me,” a record that sounds mostly like a homecoming, he seems much too comfortable to be thinking about any of this. He’s just singing, and doing that very well. Sorting through chocolate bar choices in that Southern gas station, he’s still that casual about it: “People say, ‘Oh, this isn’t weird!’ It’s certainly weirder than Brad Paisley. It’s in the eye of the beholder. I’m not worried about selling out. I’ve never even been sold-in.”

James Jackson Toth plays in quintet form at Local 506 Thursday, Aug. 28, at 9:30 p.m. Tickets are $10, and The Dutchess & the Duke opens.