The culture of outsider art can be a difficult one to navigate. Take a band like the Shaggs: three sisters - the Wiggin sisters - in the late '60s, at the behest of their deranged, overbearing father, put out an album of utterly insane music that can be generously described as rock 'n' roll. Frank Zappa famously declared them to be "better than the Beatles," despite the fact that they clearly had very little idea of how to play their instruments, let alone even the vaguest conception of what pop music was supposed to sound like.

Rock revisionists glommed onto their album and Zappa's championing praise, but once you learn of the psychological torture their father put them through in the creation of the Shaggs, it becomes hard to listen to them without feeling like a heartless creep.

Meanwhile, Daniel Johnston - while legitimately mentally ill - created music that flashed with moments of brilliance, in addition to disturbing peaks inside an unstable mind. (That he could actually play an instrument helped matters considerably.)

While Teardropcity shares some of Johnston's bloody-minded exploration of recurring themes, you'd be a fool to think that he was anything other than deliberate in what he does.

To reductively describe what Matt Wheeler, AKA Teardropcity, does, his music sort of sounds like a hip-hop/country hybrid with vocals that sound straight out of Beat Happening. But let's let the Olympia local describe it himself.

"I have several catch-phrases that I use to describe it, the first being ‘music for late nights and early mornings,'" says Wheeler. "The second being ‘contemporary American music from the future past,' the third being ‘400-year-old hip-hop,' the fourth being ‘avant garde music for the masses.' ... I think that's all of them. Sort of a combination of those."

In case you haven't already figured this out, Wheeler is a savvy guy. In exploring his albums, you find songs like "Jay Z Diss," which, despite its provocative name, is an otherwise innocuous song, a free jazz chant that doesn't quite rip Jay-Z a new one. Wheeler says he released it in protest of Jay-Z's vilification of autotune, but part of the brilliance of the Teardropcity project is this kind of self-promotion and self-mythologizing, which also manifests in Wheeler's series of bizarre green-screen music videos.

If you were to hear Wheeler's early work, an album called Unfinished Sympathies, you'd hear a very different Teardropcity. Armed only with an acoustic guitar, the Teardropcity of old shared the same affection for oddball, deadpan love songs as bands like the Magnetic Fields and the aforementioned Beat Happening. Then, inexplicably, by his next album - Really Real - Teardropcity has turned into this kind of avant-hip-hop project.

"One day I just woke up and was just like, ‘I don't want to keep making records with just me and a guitar, this very minimalist country-folk type stuff,'" says Wheeler. "I really liked doing that, and I just took it to a point where I thought, if I keep doing this, I'll be doing it just because it's the style of music I did before. I wanted to make hip-hop records. I've been a hip-hop fan my entire life, but it wasn't until a few years ago that the type of equipment was affordable to me to be able to make those kinds of records."

I describe Teardropcity as outsider art not only because of its inherent oddness - although that's a factor, too - but because I genuinely consider Wheeler to be an artist. The stuff that he's making is definitely out there, often residing at the brink of palatability, but he knows exactly what he's doing. His latest LP, hilariously titled Chinese Democracy 2: Electric Boogaloo, drops in January.

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