I’ve been thinking a lot lately about two songs in my record collection.

One is Jimmie Rodgers’ “T.B. Blues,” considered by some musicologists (e.g. Hugh Barker and Yuval Taylor) to be one of the first popular autobiographical songs. Rodgers made a career out of singing songs about other people—miners, gamblers, gunslingers, jailbirds. But in 1931, the tuberculosis he contracted at 27 years old started getting the better of him, and he became increasingly aware of his own mortality. As a result, he put out a song littered with darker themes about the loneliness of the grave and how his bones rattled like trains down the Southern Pacific. Whereas before, he might have used fictional characters to covertly portray and express his own personal tragedies and obstacles, here he puts up no fronts, speaking plainly in the first person: “When it rained down sorrow it rained all over me.”

The other song is “Oh Boy” by the band Girls, who broke up a few years ago. It’s a b-side to their early single “Laura,” and never appeared on a full album release. The subject of “Oh Boy” isn’t nearly as grim as “T.B. Blues”.  It’s just about a girl and wishing you were someone else. But the emotions – the intense loneliness and isolation, desperation and surrender – are the same. This is the sort of output that has led lead singer Christopher Owens to, on occassion, be counted among Bob Dylan and Nick Drake as an intensely personal, authentic songwriter. (Dylan’s inclusion in this group in the popular mindset is especially problematic, but that’s a separate issue in itself.)

Rodgers and Owens don’t get the stamp of authenticity just because they appear to be honest with their respective audiences. It’s not a label we would often assign, for instance, artists that sing about easy-going activities or who convey optimistic outlooks. Emotional pain, often rooted in personal failings, is a prerequisite to authenticity, and it takes an enormous amount of vulnerability and courage to express. I wonder if that’s part of the reason that male singer-songwriters resonate with me more than their female counterparts. I feel like the same burdensome expectations of masculine strength and emotion-masking that bear down on me are placed on them, and I can admire their vulnerability all the more for it.

There’s also a romanticized Americana element in Owens’ music: his love of all things country, blues, and rock and roll (essentially, the American popular canon), plus the way he comes off is akin to Elvis Costello and Brian Wilson in a very reverent, uncynical way.

All of this combined makes Headspace’s cover of “Oh Boy” an extremely peculiar statement. The band obviously admires Girls’ music because the track is semi-rare, a fairly buried b-side that casual fans likely wouldn’t encounter. In addition, they’ve made a point of not only recording a studio version, but doing multiple live performances and acoustic sessions of the song. There’s a deep respect, it seems, for Owens’ songcraft.

But Headspace’s version undermines all the romanticizations that are so important to the appeal of the original. It starts out with a standard rock intro that is quickly greeted by a nasally, seemingly insincere vocal. It doesn’t carry any of the heartbreak of Owen’s track, sounding less confessional and more Hunx and his Punx. It takes the vulnerability of the song and disguises it in a cloak of irony, allowing Headspace’s lead singer to avoid all the messy emotions that come went into Owens’ delivery.

This process of emotional dilution shapes many of the artistic statements nowadays; the adolescent sarcasm of Generation X has been replaced by the arguably equally adolescent irony of Generation Y. Everyone, on some level, has been exposed to this characteristic irony.  It’s evident to anyone that is part of this generation, and there are plenty of Salon editorials and Guardian thinkpieces to make it abundantly clear to the other generations.

The perception of what this brand of countercultural irony entails, I think, is often misguided and misunderstood. There exists a common belief that irony is destructive because it encourages the embracing of otherwise socially undesirable and perceived-as-worthless cultural items: bad music, ugly clothes, terrible trends, obnoxious hashtagging. This is somewhat true, but only if you change the emphasis of the statement, italicizing the “socially” in “socially undesirable” and “perceived-as” in “perceived-as-worthless.” See, what might be construed as the biggest problem with irony is, in fact, its biggest strength. It allows people to find value in socially-rejected cultural items. It lets people off the hook for treasuring things that they otherwise wouldn’t be allowed to treasure, without getting an earful from friends or fans for it.

I’d even posit that, contrary to common perception, the counterculture isn’t embracing these items on a superficial level as a means to a humorous end (though this sometimes happens); instead, I’d argue that it’s using humor as a superficial means to legitimately embrace these items. I’d argue that the vocalist of Headspace really believes in the power of the words he’s singing. He’s just acutely aware that sincerity can come off as cheesy, that attempts at genuine artistic expression can be belittled as juvenile, that self-expression can sometimes be met by eyerolls. These reactions hurt. A snotty delivery is the perfect tool to deflect and preclude these criticisms while still allowing him to embrace the beauty of a song like “Oh Boy.” In a strange way, this strong self-awareness has made Generation Y the post-modern generation: anxious about its every expression, output, and utterance, an anxiety likely due partly to social media’s proven effect of making its users incredibly sensitive to the expectations and reactions of their vast and diverse audience.

Of course, the tools can also be the problem. The fact that this self-awareness is social rather than personal has obvious drawbacks. And irony, as has been pointed out by Salon, can be used as a mask that prevents truth and communication, rather than a tool that fosters it – a mask that works as a half-measure, a rudimentary stop gap to allow us to actually appreciate. It can come off as cynical and disaffected, and it often prevents empathy and genuineness. Taken to an extreme, it can terminate the tradition that originated with “T.B. Blues”. You end up with artists printing and framing “Save Trees Lol” instead of striving hard to make sincere, beautiful expressions (Ripp’s recent solo show at the Postmasters gallery was a series of breathtaking oil paintings which I can’t speak highly enough of, which is why I feel mostly alright about singling out his “Save Trees” print). There’s surely a value to ironic and snotty art that I’m not going into here, I know; art isn’t all about pursuing beauty. And all of this sounds sentimental and wishy-washy, I know; it makes me want to put on a mask myself, to qualify the statement or to distance myself from embracing beauty. But, I think that very fact serves to illustrate the importance of what I’m trying to say.