In many ways, Elliott Smith’s performance of “Miss Misery” at the 1998 Academy Awards stands as one the most surreal moments in the award show’s history. Standing alone on a massive stage, adorned in a blindingly white suit, black shoes and that egg-shell voice hiding behind an acoustic guitar, Smith’s introduction to mainstream America could not have come in a stranger setting. His music was and is designed for quiet, contemplative listening either late at night with a small group of friends or alone on a bleak mid-winter’s day. The heart-wrenching sincerity with which he sang and performed stood grossly at odds with the gaudy superficiality of that Hollywood spectacle.

That it lost to the then-ubiquitous “My Heart Will Go On” came as no surprise to anyone in attendance (a sentiment personified by Madonna’s snide remark before revealing the winner) and was of little consequence in the grand scheme of things. Elliott Smith was never meant for such a grand stage, nor would he have felt comfortable embracing such an image. Losing the Oscar was the best thing that could’ve happened to him at that point – the worst having already come to pass in the song’s nomination and subjection to broader public scrutiny. It went beyond mere appropriation of an underground hero by a mainstream audience, feeling instead like something special, something too precious to be made into a public spectacle, having been ripped from our grasp and thrown to the wolves.

He rarely looks up during that performance, either out of fear or ambivalence or just a general sense of disbelief at what is unfurling before him. He looks so small when he returns to the stage for an obligatory bow, unsure of himself and uncomfortable in the situation. And yet it was this very moment and the exposure afforded him by the song’s success that allowed him to make the album with the backing of a major label that would come to define his musical legacy and showcase the full brilliant potential of his pop genius.

Like any great and truly transformative album, XO exists wholly out of time and space. Sure, it was released in late summer 1998, more than half a year after his Oscars performance. But that’s a concrete fact that misses the point entirely. XO sounds like nothing else released that year, instead sounding like an amalgamation of the best post-Beatles pop music the world had to offer. Gorgeously adorned and sumptuously arranged, the songs of XO find Smith rising to a new level of adventurousness. But at the heart of each is exactly that which had been found on his previous, stripped-down releases for venerated indie label Kill Rock Stars: great fucking songs.

It’s long been the hallmark of the best songs, that ability to be presented both fully orchestrated and stripped to their barest essentials and still manage the same level of emotional resonance. Opening track “Sweet Adeline” retains the formula of Either/Or, Smith’s hauntingly fragile voice floating atop an intricate acoustic guitar line and bleak lyrics. But as it nears its conclusion the song explodes into Technicolor glory showing Smith to be a die-hard Beatles fanatic at his maudlin core. The rest of XO unfolds largely the same, Smith, like Dorothy before him, leaving behind a black and white world for something far more brilliant and magical.

“Tomorrow Tomorrow” manages to keep things sparse, but no less biting in its bittersweet lyrics (“Noise is coming out, and if it’s not out now, then tomorrow/ Tomorrow they took your life apart and called your failures art/ They were wrong though they won’t know ’til tomorrow”), while “Waltz #2 (XO)” may well be the quintessential distillation of everything that made Smith such a remarkable performer. That crushing chorus of “I’m never gonna know you now/ But I’m gonna love you anyhow” couched in a gorgeously coruscating melody is pure pop perfection, emotionally gut-wrenching and infinitely catchy. Building to a massive, explosive crescendo, “Waltz #2 (XO)” is pure musical catharsis.

“Everybody Cares, Everybody Understands” ventures down similar territory, stripping the poeticism of “Waltz #2 (XO)” to something more bleakly matter-of-fact: “Everybody cares, everybody understands/ Yes everybody cares about you/ Yeah and whether or not you want them to.” It’s a sentiment that could well serve as the epitaph of any tortured artist, but Smith takes it one step farther, exposing himself just that much more. “You got a pretty vision in your head/ A pencil full of poison lead/ And a sickened smoke illegal in every town,” he sings, the autobiographical nature of the lyrics plainly displayed.

But it’s the rejoinder that proves to be the punch to the solar plexus that takes the song to the next level: “You say you mean well, you don’t know what you mean/ Fucking ought to stay the hell away from things you know nothing about.” In other words, I appreciate your concern but you’ve no idea what I’ve been through, am going through, will continue to go through. It’s both a personal missive and one seemingly delivered to the public writ large.

Lyrically, XO essentially lays out the remainder of the Elliott Smith story, one seemingly scripted to perfection, playing into mythic persona he simply could no longer inhabit. Yet unlike similarly maudlin performers, Smith’s art was in no way artifice, instead an unprecedented look into his psyche. Were we all paying closer attention, we could’ve seen how the story was destined to end. There would be no happy ending, Smith becoming the embodiment of his own songs in both life and, eventually, death.

This would reach its ultimate conclusion with his death five years later – suicide, a knife to the heart. It was a final act that could not have been more Hollywood in terms of its dramatically poetic nature. Too fragile to exist on this mortal plane, Smith’s brutal exit in October of 2003 put a heartbreaking end to a career built on heartbreak and loneliness. Ultimately, he proved, like Nick Drake, his closest musical antecedent, his songs were no mere affectation and instead his literal heart and soul on display for all to see and hear. If only we’d listened more closely and intently at the time.

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