If I could only take four albums from the 1990s on a desert island with me, this would be one of them. How else could I process all the loneliness? 

4. Elliott Smith – XO (1998)

There’s a generally agreed-upon theory when it comes to vocal harmonies – nothing sounds better than two blood relatives singing together. And there’s a bevy of DNA-sharing crooners to back up this “blood harmony” argument (e.g. the Everlys, Andrewses, Wilsons). But in 1998, Elliott Smith released an album stuffed with dazzling vocal harmonies, without a family member on hand. It was perhaps a depressing exception to the rule. Because the only person this artist wanted to sing with was himself.

After releasing a trilogy of quietly devastating folk albums on indie labels, Smith unexpectedly blew up when director and fellow Portlander Gus Van Sant caught wind of him, using six of his songs on the soundtrack to his movie about how hard it is to be a handsome white genius, Good Will Hunting. The track “Miss Misery” got an Oscar nomination alongside the likes of Celine Dion and Faith Hill. And Smith performed it on the telecast, with artfully mussed hair and a white suit, looking tentative but sounding absolutely at home with the melodic flourishes of the pit orchestra.

After this unforeseen dalliance with the mainstream, it was time for Smith to make good on all the attention, and elevate his game in the recording studio. He was more ready than it may have seemed. The singer/songwriter’s willingness to sound vulnerable on tape didn’t mean he didn’t know how to take control – he spent five years leading the alt-rock band Heatmiser, which landed a contract with Virgin in 1996, right before Smith’s solo career became too big to ignore. So while the songs on XO are rooted in feelings of inadequacy, the arrangements are the work of a confident artist coming into his own.

Take the bridge of XO’s first single, “Waltz #2,” for example. The song is a poetically veiled story about Smith going to a bar karaoke night with his mom and stepfather. He no longer recognizes her, and tries to brush off being triggered by him. All over a waltz tempo sprinkled with rickety saloon piano runs. Which builds to the bridge, a heartbreaking sigh of resignation:

I’m here today and expected to stay
On and on and on
I’m tired

Musically, Smith treats this moment like a rocket launch. The band revs its engines to the first line. Then his multi-tracked vocals reach higher and higher with each ensuing “on.” As we arc back down to earth, our narrator might be tired, but us listeners are inspired. XO is loaded with dissonant moments like these, beauty and sadness spiraling into one another until they’ve bonded. It’s a forensic analysis of what a big fucking mess life can be, delivered in perfect pitch.

All of it is anchored by Smith’s underrated guitar playing. Years spent recording alone into four-tracks honed his chops to the point where he could play the chords, bass line and lead melody simultaneously, giving himself and co-producers Rob Schnapf and Tom Rothrock fully formed blueprints to build on. The opening “Sweet Adeline” relies on little more than his bouncing acoustic melody for a full 90 seconds, before the dam breaks and the drums, piano and backing vocals drown us. And his finger-picked intro to “Independence Day” is so deeply, fluidly melodic, it could’ve worked as an instrumental.

But that first blast of full-bore instrumentation in “Sweet Adeline” showed us that XO was not going to be another tape-hiss-heavy, stripped-down affair. Smith, an avowed Beatles fan, was ready for his big, Revolver-style, studio-driven artistic evolution. And he sealed the deal with an album closer that’s every bit as jarring as “Tomorrow Never Knows.”

“I Didn’t Understand” finds Elliott Smith alone. No instruments, no guest vocalists, a lyric sheet that gives him nowhere to hide. The only sound is his voice, stacked to the heavens in an audacious display of vocal harmony. It begins with yet another majestic sigh, a parishioner in a confessional clearing his throat before laying himself bare. And then he begins, singing in his uniquely cryptic way about a breakup, mostly about how much he deserved it:

And so you’d soon be leaving me
Alone like I’m supposed to be

Then, with the vocals-only arrangement underlining the stakes – intricate waves of beauty when he exhales, nothingness when he inhales – Smith ends his song with a stanza that will crush anyone who has been too stupid or self-absorbed to realize that somebody was right there in front of them, needing them:

You once talked to me about love
And you painted pictures of
A Never Never Land
And I could have gone to that place
But I didn’t understand

A short five years after XO cemented his genius, Elliott Smith left us. But not before he showed us how beautiful it can be to create your own sense of harmony.