The 10 Best Elliott Smith Songs

By Scott Lapatine / August 22, 2012

Elliott Smith was born on August 6, 1969, and thus, August is Elliott Smith Month, according to his onetime label, Kill Rock Stars. To celebrate, KRS has been generously offering fans alternate versions of some old Elliott tracks: previously unheard versions of songs that appeared on Smith’s 1995 and ’97 releases, Elliott Smith and Either/Or, respectively. It’s been a bittersweet experience, hearing anew these songs that have been etched into our collective memory. Not only do they remind us of the talent lost, but they capture the artist just as he was approaching the peak of his abilities, when his promise still eclipsed his artistic output (to be sure, though, his artistic output was already estimable). Hearing that new-old music left me hungry for more, eager to revisit Smith’s catalog, to sort through some of my own feelings about the man. And that left me here, collecting my thoughts, making this list.

Before we begin, some notes about my methodology, and a confession.

Elliott Smith released five solo albums before dying in 2003; 2004 brought the posthumous From A Basement On A Hill, the album Smith was working on when he died, and in 2007, Kill Rock Stars gave us the two-disc New Moon set, which compiled previously unreleased material Smith recorded during his time with the Portland label. He also released three albums with his indie-rock band, Heatmiser. Then there are officially sanctioned non-album tracks, and countless bootlegs offering material that has yet to see the light of day via label release.

For this list, I considered for inclusion all (and only) officially released Elliott Smith solo material, album and non-album: no Heatmiser; no bootlegs. I saw two options in terms of approach: I could have made a list that took into account all phases of Smith’s career, or I could have spotlighted what I truly believe to be his 10 best songs. I went with the latter. This made the task much more difficult — Option A would have created some handy processes of elimination, taking out of my hands some tough choices — but the final product is, I hope, more honest.

Of course there are inherent problems in trying to view Smith’s career through such a limited scope. Smith’s musical ambitions and abilities evolved so rapidly and distinctly that trying to judge ES MK 1 against ES MK 2 or 3 does a disservice to all that material. On his first two albums, 1994’s Roman Candle and ’95’s Elliott Smith, the artist was subdued, shy. The albums function best as albums; the songs flow and blend into one. (It’s no coincidence that almost half the songs on Roman Candle are titled “No Name.”) Much of 1997’s Either/Or retains the modest beauty of those records (another “No Name” here), but tracks like “Ballad Of Big Nothing” and “Pictures Of Me” — which feature ferocious pop choruses and robust instrumentation — provide a roadmap for Smith’s eventual direction. On 1998’s XO, Smith moved from Kill Rock Stars to major label Dreamworks, brought in collaborators like Tom Rothrock and Jon Brion, and created an album bursting with ambition and melody, an album that is carefully constructed and arranged. To sort of borrow his own metaphor, in ’94 and ’95, Smith was shooting off Roman candles; by ’98, he was putting on fireworks displays. He followed that with 2000’s Figure 8, more baroque even than XO — bigger, bolder, weirder still — although much of Smith’s sweetness and reticence was buried in the elaborate productions.

Elliott Smith died in October, 2003, reportedly the result of self-inflicted stab wounds. The music released posthumously showcases Smith at his artistic extremes: From A Basement On A Hill picks up where Figure 8 left off, more or less; New Moon has the same spare beauty of those early albums.

It’s essential to note the very specific connection between Smith and the individual listener. Elliott Smith wrote intensely personal songs, and his fans feel an intensely personal connection to those songs. I mention this because I’m an Elliott Smith fan, and as such, my own bond with the artist is necessarily different than yours. I discovered Elliott Smith in 1996, when I was interning for the publicity company working his then-new self-titled album. One of the publicists at that office knew I had a fondness for deeply depressing music, so he gave me a cassette sampler, with Elliott on one side, and the Softies on the other. I was pretty quickly a convert: I identified with Smith’s introversion, his awkwardness, his sadness, his rage, his self-destructive impulses. (I remember when Smith came to NYC to do some press, one of the junior publicists was tasked with staying with him, at all hours, to keep him away from whiskey. Just whiskey. Anything else could be managed. But not whiskey.) I was also touched deeply by the wonder and beauty in his music, which invited me to get comfortable, get to know this person, lose myself.

When Smith moved from Portland to Brooklyn, where I lived at the time, my feeling of connection intensified. My misery now had company. I knew he spent days at Brooklyn bars, writing lyrics and drinking, and even though I did not expect to run into him, it brought me some degree of comfort to imagine him a few miles (or blocks!) away, lost in booze and words. When he left Brooklyn for Los Angeles, a city I had been conditioned to dismiss as vacuous and culturally empty, I felt betrayed. It was an irrational reaction, of course, but a strangely intense one. I’ve never been able to fully embrace his L.A. album, Figure 8, for exactly that reason. I saw him live twice: once in 1997, at Brownies, where he was magnificent; once in 2003, at Bowery Ballroom, opening for Jon Spencer Blues Explosion, where he could barely play a full song. He fumbled, sheepishly, clumsily. I sneered; I blamed L.A. He died nine months later. I’ve never fully accepted his death, and I’ve had trouble listening to his posthumous releases.

These are my biases, just as you have yours. But I stand by the selections below. I only wish there were more.

10. “Roman Candle” (from Roman Candle, 1994)

After two albums of squealing, frenetic indie-punk with Portland’s Heatmiser, Elliott Smith’s decision to record a solo album must have initially seemed like something of a lark: the type of sensitive singer-songwriter stuff that rock frontmen do in their spare time to decompress and make use of material not suitable for the real band. But that album, 1994’s Roman Candle, surely put to rest any such notions pretty quickly. The album opens with its title track, which is immediately more compelling and powerful than anything Heatmiser had recorded to that point. Structurally, the song is bare-bones, lo-fi: two guitars, one acoustic and one electric, and one vocal track doubled up on the chorus. The guitars quiver like hummingbirds, and Smith’s vocal trembles above them, a whisper that attempts to contain rage more than convey intimacy. The chorus is cathartic and unforgiving; sings Elliott, “I want to hurt him / I want to give him pain / I’m a Roman candle / My head is full of flame.” In 3:37, it captures perfectly the quiet torment that will come to plague most of Smith’s narrators and protagonists over the next eight songs and five albums.

9. “Tomorrow, Tomorrow” (from XO)

By XO, Smith had basically elevated his guitar game to virtuoso levels, and there’s absolutely no better example of this than “Tomorrow, Tomorrow,” a gorgeous, multilayered production worthy of Brian Wilson, at the center of which is Smith’s intricate, fleet picking. It’s probably the single best-sounding song in his catalog (although much of XO could qualify for that title, and no other Elliott Smith album sounds anything like XO). The lyrics are much darker than the music, voicing fear and frustration with the music industry, and more troublingly, with writer’s block and failure: “I got static in my head / The reflected sound of everything / Tried to go to where it led / But it didn’t lead to anything.”

8. “Baby Britain” (from XO, 1998)

Elliott Smith’s much-noted love of the Beatles grew more apparent in his music as his songwriting progressed, and it reached an apotheosis in “Baby Britain” (there’s even a Revolver reference in here!), possibly the catchiest and most buoyant track in his catalog. The exact subject of the lyrics is unclear, but alcohol is clearly involved; I’ve always read it as an account of two friends spending a long night at a bar, boozing and talking, the narrator frustrated by his partner’s self-pity. It’s also a great drinking song about drinking — fun to sing along to, the lively piano making everything seem more vibrant. Sings Smith: “We knocked another couple back / The dead soldiers lined up on the table / Still prepared for an attack / They didn’t know they’d been disabled.” I can’t tell you how many times I’ve sung those own lines to myself as the dead soldiers amassed around me.

7. “The Biggest Lie” (from Elliott Smith, 1995)

Elliott Smith had a practice of closing his albums with the lightest, gentlest song — perhaps in some way to provide an easier transition to reality for the listener after 40-or-so minutes of dark, hard emotions addressed in rather specific detail. “The Biggest Lie” is the last song on Elliott Smith, and his loveliest album-closer (no small accomplishment when the competition includes “Say Yes” and “I Didn’t Understand”). On the surface, it’s a straightforward, immensely sad breakup ballad. The guitar isn’t especially intricate, the melody is direct and very catchy, and the lyrics appear to simply lament the dissolution of love. That said, it’s an unusually vague song for Smith, and there’s plenty of subtext to decode: It could be about how a shared addiction destroyed the narrator’s relationship; it could be about suicide (or, more generally, death). But when Smith sings, “Oh we’re so very precious, you and I / And everything that you do makes me want to die,” the implied meaning becomes irrelevant — it’s about as viscerally affecting and emotionally resonant a moment as music can produce.

6. “Needle In The Hay” (from Elliott Smith, 1995)

“Needle In The Hay” opens Elliott Smith, and it has a lot in common with the album-opener that preceded it — it’s quiet, minimalist (just acoustic guitar and voice), and its rhythm is like a heart palpitation. Still, Smith had made clear leaps already, finding new confidence in his already abundant gifts, namely his ear for melody, his intricate guitar work, and his detailed lyrics. Here, the razor-sharpness of Smith’s words draw blood. The song is a portrait of heroin addiction told from two perspectives: first, the junkie’s enabler (probably his father, based on the line, “He’s wearing your clothes / Head down to toes, a reaction to you), and then, the junkie. Not a word is wasted, as the song gets darker and darker, until the crushing last line of the last verse: “You ought to be proud that I’m getting good marks.” The “marks” here are track marks, the play on words intentional and mean spirited; the “You ought to be proud” is a sarcastic “fuck you” to the person who looks on, frustrated, bewildered, scared, and angry as the person they love is “strung out and thin / calling some friend trying to cash some check.” It’s bleak and harrowing storytelling, delivered with enviable deftness and grace.

5. “Between The Bars” (from Either/Or, 1997)

It is, of course, impossible and irresponsible to try to determine the degree to which Elliott Smith’s songs are autobiographical, but considering his known bouts with numerous demons, it’s hard not to see “Between The Bars” as a cry for help. Sonically, it is perhaps the gentlest track in Smith’s catalog — a lullaby, or a serenade — but beneath the surface, the lyrics describe the numbing, destructive lure of alcohol, as understood by an alcoholic. The first line could be an invitation to party — “Drink up, baby, stay up all night” — but it soon becomes clear that the narrator doing the coaxing is alcohol itself: “Drink up with me now / and forget all about / the pressure of days / Do what I say / and I’ll make you okay / and drive them away / the images stuck in your head.” It’s one of five Smith songs included in Good Will Hunting, and it’s actually featured twice in the film: an orchestral version and the bleak original. Nothing in the film approaches the darkness of the song’s subject matter, but there’s a certain warmth here, too, that actually makes sense in such a role — “Between The Bars” doesn’t treat alcoholism as a thing to be feared; more like pleasant place from which to watch ambition slowly atrophy.

4. “Condor Ave.” (from Roman Candle, 1994)

While most of Roman Candle was the work of a massively talented but unformed artist, “Condor Ave.” is an example of Smith momentarily achieving the huge potential he would reach pretty regularly on his next three albums. Smith’s shuffling, lovely guitar-playing and sweet melody are sharper here than they are anywhere else on the album, but more thrilling are his lyrics, which are worthy of Raymond Carver, and the flow with which he delivers them, which makes these exactingly crafted verses jump from Smith’s tongue as if they were spontaneous. The first verse, in which the narrator recounts the moment his lover drove out of life, is nothing short of perfection: “She took the Oldsmobile out past Condor Avenue / and she locked the car and slipped past / into rhythmic quietude / Lights burning / voice dry and hoarse / I threw the screen door like a bastard back and forth / The chimes fell over each other / I fell onto my knees / The sound of the car driving off made me feel diseased.” From there, things get really fucked up. The driver, exhausted, falls asleep at the wheel, accidentally killing an old alcoholic who’s sitting on the side of the road. The driver takes off, leaving behind a police investigation and a spurned lover who’s caught between confusion and rage. It’s compelling, breathtaking storytelling, delivered in one of Smith’s prettiest arrangements.

3. “Division Day” (from the “Division Day/No Name #6″ 7″, 2000)

Initially released as the front half of a double-A-side 7″, “Division Day” was a like a marriage of Elliott Smith’s Kill Rock Stars material and the much-more robust music he produced on XO and beyond (fitting that it was released on neither KRS nor Dreamworks, but the comparatively tiny Seattle-based Suicide Squeeze). It has the fuller arrangements and instrumentation Smith explored on his Dreamworks albums, but the lo-fi intimacy of his earlier work — and for that, it’s truly exceptional. Its also just a magnificent song. Driven by a rollicking piano and one of Smith’s most exuberant vocals, the song recalls “Sweet Jane” or “Good Day Sunshine”; sonically, it’s an expression of pure joy. Lyrically, it’s one of the most disquieting and confessional moments in Smith’s catalog. Some biographical background: Smith claimed to have been molested by his stepfather, which led to Smith moving out of the family’s Texas home at age 14, and moving in with his father in Portland, Oregon. (As an adult, Smith got a tattoo of Texas on his arm, about which he said: “I didn’t get it because I like Texas — kind of the opposite.”) The lyrics of “Division Day” seem to document that awful time in Smith’s young life: “Mostly they’d meet when he was asleep / and have some sick exchange / that struck him as wrong and moved him along / closer to division day.” The “he” in this scenario is probably Elliott, the “sick exchange[s] that struck him as wrong,” are likely sexual encounters with his stepfather, and “Division Day” would then be the day he moved away from his mother. I swear, it sounds like such a happy song.

2. “Angeles” (from Either/Or, 1997)

One of Elliott Smith’s most-beloved and best-known songs (due, in no small part, to its inclusion on the Good Will Hunting soundtrack, the place many fans first heard Elliott Smith), “Angeles” is the quintessential early-Smith composition: hushed, layered vocal delivery; dueling acoustic guitars; a rhythm that seems both furious and still. Lyrically, it defies easy interpretation. It could be about gambling or drug addiction, though it reads most logically as a discussion of the Faustian bargain that once came with being a musician moving from an independent label to a major. The “someone” in the first line (“Someone’s always coming around here, trailing some new kill / Says I’ve seen your picture on a hundred dollar bill”) is probably an A&R rep, of whom Smith’s then-home (the Pacific Northwest) saw their share in the ’90s. Then, of course, there is the promise made by that someone (“I could make you satisfied in everything you do / All your secret wishes could right now be coming true”) and the fine print (“And be forever with my poison arms around you”). Honestly, that’s probably what the lyrics are about. But it’s such a powerful, immediate song — it resonates so vibrantly with listeners — that its lyrical intention is almost irrelevant; it means what the listener hears, what the listener needs it to mean. Faustian bargains are in no way limited to art and commerce, and “poison arms” wrap around us in shadows and alleys everywhere.

1. “Waltz #2″ (XO) (from XO, 1998)

Ambitious, bold, intoxicating, and beautiful, “Waltz #2 (XO)” is the apex of Elliott Smith’s career: the fulfillment of every promise ever made by his Kill Rock Stars records and then some. Rhythmically, the song is indeed a waltz — written in 3/4 time signature — and listening to it, it’s not hard to imagine a room full of couples dancing close, drunk, alive. Again, all of Smith’s lyrics are open to individual interpretation, but this one seems pretty obviously about his mother, his mother’s decision to build a home with Elliott’s allegedly abusive stepfather (“That’s the man she’s married to now / That’s the girl that he takes around town”), and Elliott’s decision to leave (“I’m so glad that my memory’s remote / ‘Cause I’m doing just fine hour to hour, note to note”). The bridge is one of the most aching and moving moments of music in a catalog that is entirely aching and moving, as Elliott sings of the prison-home provided by his mother, “I’m here today, expected to stay on, and on, and on,” his voice going higher and higher. But again, the intention of the song has been erased by its audience, almost surely for the better. When Elliott sings, “I’m never gonna know you now, but I’m gonna love you anyhow,” he’s singing to his mother, the woman whose choices forced him to leave. But since his death, the subject has changed. Now, it’s us singing to him, individually, imagining what was lost, reading between the lines, feeling grief and anger and frustration, never knowing, but loving him anyhow.

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You can also listen to our playlist of Elliott Smith’s 10 Best Songs on Spotify.