ON A SWELTERING summer afternoon at the outskirts of the Portland city limits, Joe Pug performed in a barn. Its best oscillation days behind it, a lone fan pushed the thick warm air around the dusty walls of the structure as the unassuming Chicago folksinger (born Joe Pugliese) took the stage looking like some lost ranch hand attempting to work up a stake in a Steinbeck novel. While the barn itself was just another makeshift venue for the sprawling Pickathon festival, Pug was not your predictable folk singer.

As his small frame twitched and swayed, Pug's face winced with every word he delivered in a voice far older than his age of 25 years. Stark and vulnerable, his singing voice resided in some sort of mythical crossroads between Zimmerman and Dylan, or the more introspective moments of Oregon's own black sheep boy, Tim Hardin. To a sparse yet stunned crowd with locked gazes and jaws agape, Pug sung makeshift hymns ("Hymn #101"), channeled Phil Ochs at the '68 Democratic Convention ("I Do My Father's Drugs"), and sent a collective chill down our spines while delivering the line, "I undressed someone's daughter then complained about her looks" ("Not So Sure") with a casual ease. It was in that moment, sitting cross-legged on the dirty floor of a barn, that every single occupant of that room became a believer in Joe Pug.

"I play a couple hundred shows a year, that's kind of the game plan," Pug explains while manning the wheel and embarking on yet another long drive touring the States. "I don't know how people do it otherwise. It's really the only way to get your music out there and, for me, it's the only way to stay employed and make a little bit of money." If this is a gauge of success, it's working; Pug recently upgraded his touring vehicle from an air conditioner-less 1995 Plymouth Voyager to a modest Grand Voyager touring van. Hardly a portrait of an artist enjoying a financial windfall, but with one full-length under his belt—the just-released Messenger—and two EPs (one available for free online), it's a modest foundation to build upon. Especially after he gave away thousands of CDs.

Eager for someone—anyone, really—to hear his music, Pug's earliest days were spent putting tongue to envelope and mailing off free sampler CDs and handwritten notes to anyone who promised to listen. While the total number of mailed samplers is unclear, it's been reported that Pug mailed off over 15,000, which comes as news to him. "I have no idea how many we've given away at this point," he explains. "I'll put it to you this way: They definitely know our faces at the post office. We can actually just walk in the back door right now and just dump 'em in the bins."

The modest start of this bedroom music's distribution through the postal service planted the seeds for a dutiful following, and eventually led to tours alongside peers such as M. Ward, Josh Ritter, Steve Earle, and even a current stretch with his former tourmate's own flesh-and-blood, Justin Townes Earle. This tour comes to Portland on Valentine's Day, for which Pug is prepared. (Well, at least as prepared as a songwriter in the habit of penning soul-smothering ballads for the emotionally damaged can be.) "We'll have to do something special," he admits. "In that case, I won't play any breakup songs—even though that's probably half my catalog right there."