In summer 2003 I woke at 4am every day for a month, and walked through sleeping suburbs as the sun came up. Those mornings, pushing a vacuum cleaner through the quiet halls of a crumbling primary school, I first came to know Elliott Smith on Either/Or, his second full-length under his own name. I didn't understand right away. This was music at complete odds with everything else I was listening to at the time. It was husked in a quiet voice, but poppy, in a way I later came to recognise as owing a lot to The Beatles. There was barely a lick of distortion on it. It could be bouncy at times, but the more I listened, the sadder it got.

A few months later, in a newsagent's, the front page of NME announced to me that Elliott Smith was dead. I won't pretend that I felt anything other than a small and swiftly passing sadness. I did not know Elliott Smith, and I'm no closer to knowing him eleven years, ninety-something songs, and numberless repeat plays later. But his music has shaped parts of my life and view of the world around me, as well as those of some of my friends, beyond the reach of any other musical artist. I've one compadre who summed up her relationship with Smith's music by saying "no matter how deep the hole, he always throws me a torch" and that she's still here and smiling is evidence enough for me. Elliott Smith's first album Roman Candle is 20 this week. I've made it a birthday playlist.

Plainclothes Man

There are cuts I prefer from Heatmiser's final record Mic City Sons (not least the opening 'Get Lucky', where Smith bares his teeth in a way that he wouldn't really again until From a Basement on a Hill), but 'Plainclothes Man' is the best example of the man's unerring genius with a chord sequence from his pre-solo recordings. This could've been on any of his records from XO forward.

Roman Candle

So yeah, happy birthday. His first real introduction to the public is still the most nakedly angry that I've heard Elliott Smith, for all the bombast of his later records. He operates just barely below explosion on 'Roman Candle', muttering threats that, like so many of his sentiments, sound painfully futile.

Last Call

Despite Roman Candle's none-more-lo-fi production, even here it was obvious that Smith had a penchant for layered arrangements, something that he'd build on record by record. For me, 'Last Call', and especially its closing harmonies, are the first hint we get of Figure 8.

Needle in the Hay

You know this one. It's a dorky thing to say, but I always liked Smith's right hand on this, his thumbed downstroke that often gets overlooked in deference to his celebrated fingerpicking. If Johnny Cash's rhythms sound like a freight train, many of Elliott's are like motorway dash lines speeding past in the dark. Also wins 'Best use of Elliott Smith song in a film'. What? Who's 'Miss Misery?'

The Biggest Lie

Elliott Smith's other bookend. It's hard for me to pick songs from this record - it's my favourite, and I love every cut on it - but as far as 'sad song with acoustic guitar and voice' goes, I don't think that there are many better than this, a textbook example of how Smith's way with chords sets his songs apart from his ocean of contemporaries and acolytes.

Between the Bars

I was barely sixteen when I first heard this weird, abusive love song, and I had never really been drunk before, let alone come to treat booze as any sort of safety net. I hope to fuck I'll never properly understand it.

Angeles

I'm pretty sure that if you're this far in, you know how this song sounds. One of my favourite things about Elliott Smith is how he bypasses any notion of sarcasm being sneering, a self-defense mechanism - with him, it always sounds beaten, matter-of-fact, like there's no other valid choice of rhetoric in the face of a world's worth of bullshit. As Roddy Doyle once said of Bukowski, 'All power. No drama.' Very high up in the 'Best Songs Ever Written' stakes.

Cupid's Trick

Probably not about to be included in any 'best of' playlists any time soon (especially considering the calibre of the record it's from), but 'Cupid's Trick' is Either/Or's one moment of searing volume, another prescient snapshot of Smith's later work. And what a fuckin' lead break.

Waltz #2 (XO)

I'd imagine that contemporary fans of Either/Or would've been astounded by truckload of new sounds Smith had started folding into his music on this, the first single from third record XO. The studio version is miles from Either/Or's bare production, layered with guitars, pianos, big harmonies, and progress is good, right? Well, I don't really give a shit about progress. What I really give a shit about is when Smith sings 'I'm tired' around 2:33. I never had less trouble believing someone.

Independence Day

I didn't properly explore Elliott Smith beyond Either/Or for nearly four years after first hearing his music. This was the song that brought me back in. As well as being a studio curiosity (it's built around a Tom Rothrock drum loop, rather than a live kit), it's one of Smith's most ambiguous cuts lyrically. I've always chosen to frame it as optimistic.

Waltz #1

Often overlooked compared to its namesake, I think that this is one of the most beautiful pieces of music that Elliott Smith ever committed to tape. 'Everything Means Nothing To Me' on Figure 8 always seemed in a similar situation.

Junk Bond Trader

Perhaps the only time that a harpsichord has sounded OK in a pop song. On Figure 8, Elliott Smith announced to the world that he could make a whole record of massive, glistening radio-rock if he damn well felt like it, and 'Junk Bond Trader' (more than 'Son of Sam' and even 'LA') is my favourite of these cuts.

Everything Reminds Me Of Her

But, yeah, he could still palm out an effortless acoustic song that got right to the nub of a broken relationship's aftermath.

Easy Way Out

I wouldn't have included this here six months ago, but that's only testament to the continuing power of Elliott Smith's songwriting. I've been listening to Figure 8 for the best part of a decade, and always tended to write off its second half after the towering glory of its first. Stumbling to the shower one morning early this year, I caught this song (which I'd listened to plenty of times before) drifting from my flatmate's room. I had it on repeat for weeks. No matter how much time you spend in the company of Smith's songs, they never stop sneaking up on you.

Coast To Coast

Even after Figure 8's maximalism, the growling volume of 'Coast To Coast' came as a surprise, the filthiest we'd ever heard Elliott Smith under his own name. From A Basement On A Hill's hellish production, all its murkiness and fire-and-brimstone overdrive, might not be intentional, or even a subconscious by-product of its author's state of mind. I guess I just never much believed in coincidence.

King's Crossing

Watching the grainy fan footage behind the link above feels a bit like voyeurism compared to the stomping, synthy roar of the album cut, which goes some way to deadening the song's lyrical impact. Behind all that studio sludge, the lines "it's Christmas time and the needle's on the tree/a skinny Santa is bringing something to me" or "I don't care if I fuck up, I'm going on a date/with a rich white lady, ain't life great?" sound like abyssal humour. In this video, I'm not so sure.

Twilight

The saddest song I have ever heard.

Thirteen

One reason that our favourite artists are our favourite artists is because they end up introducing us to so much more music than their own. I think this version knocks Big Star's on its behind, but that hasn't stopped me falling head-over-arse in love with No. 1 Record.

New Disaster

Choosing original cuts from New Moon is difficult, owing to space constraints - it's a double album, and most of it's brilliant. I'd earmarked 'High Times' (whose fury simultaneously denies and confirms its narrator's drug problem) and depression-song endgame 'Going Nowhere' for inclusion here, but in the end decided on this, for two reasons. Firstly, it's a beautiful, haunting song built around the lyrics "I wonder what it is you're after/keeping company with this disaster?" If you've never asked someone that question, at least in your head, we're listening to Elliott Smith for different reasons. But also, it's the only song on New Moon pieced together from two different takes on two different tape reels. I like that. Even spliced together from disparate parts, his songs sound better than the first five that his last.fm radio would recommend you.

Half Right

I also like that New Moon finishes up with this, a stripped-back recording of the song that also closes Heatmiser's Mic City Sons. It lends a sense of the infinite to New Moon's tracklist, a sense that Smith's music never really ends, just keeps ringing out, echoing back upon itself, weaving in and out of our lives. That my first meeting with this song came in Jimmy Eat World's 'Kill', or that I've only ever seen 'The Biggest Lie' live as covered by Kevin Devine, or that RJD2 saw fit to sample 'I Didn't Understand' on 'Ghostwriter' is fitting; like the restoration of the Figure 8 mural, it's so easy to intertwine our own narratives with Smith's. Give me a good reason not to do it.