Ten bucks says Owen Ashworth can make you cry in under two minutes.

With a couple of crummy Casios and his trusty 4-track, the 28-year-old film school dropout has built a decade-spanning career out of drawing tears at rapid speeds. Armed with two-minute synth-pop songs and a husky, Prozac-induced voice, Ashworth (a.k.a. Casiotone for the Painfully Alone) has brought to life a trilogy of melancholy mini-epics: Answering Machine Music, Pocket Symphonies for Lonely Subway Cars, and Twinkle Echo.

With 2006’s Etiquette (Tomlab), Portland’s favorite saddo ups the ante, tossing the “bedroom producer” shit to the curb and fleshing out his somber skeletons with studio flourishes and guest musicians. Teeming with the saddest stuff (bad moms, lonely holidays, growing up, and growing apart), Etiquette perfects the dismal honesty his fans have come to expect.

Even so, the affable Ashworth is not comfortable calling his music depressing. “I don’t know if ‘depressing’ is the right word.” He pauses. “I really forget that the songs are so sad. But every once in a while someone will sit me down and make me listen to one of them, and I’m like, ‘Yeah, that’s a fucking depressing song.'”

Writing tearjerkers wasn’t something Ashworth just stumbled upon; it’s what he set out to do. After starting his one-man band in 1997, Ashworth set forth a slew of guidelines for himself to follow, in hopes that rules and regulations would “make songwriting as efficient as possible.”

Those limitations: Everything was to be written in the key of C, thereby rendering the black keys useless; songs were to begin and end with the vocals, because Ashworth considered anything before or after that superfluous; all music was to be created with battery-powered Casios, because, well, that was cool; and, finally, everything had to be totally glum.

Nowadays, most of those rules aren’t as important, but Casiotone still jerks tears with the best of ’em. “I grew up with Prairie Home Companion and bluegrass,” says Ashworth. “I think the tradition of American folk songwriting is based in some incredibly depressing songs. Like the Carter Family–someone is always dying of starvation, and those were always the songs that sounded legitimate to me, [they were the ones that] sounded compelling and sincere.”

Much like the country music of his youth, Casiotone for the Painfully Alone songs are light on decoration and heavy on pathos. He traffics in the most direct and honest space songwriters can: our darkest, most depressing days.

“I’ve written songs that were happy for other bands,” says Ashworth. “But something about Casiotone, something about the form of it, [made me want] to write songs that were generally dark. And even if they were kind of happy-sounding, elements of the songs should seem true to human experience. Nothing that really happens in life is 100 percent sad or 100 percent happy, and I wanted to use that gray area.”