Elliott Smith’s solo career began in a basement on a hill, with little more than an acoustic guitar and a four-track recorder. By the time he recorded his final, posthumously released album, From A Basement On The Hill, he was in a studio on a major label’s dollar, rendering his songs in Technicolor with keyboards and strings. But the beating heart of his work, from the first song he recorded to the last, was his ability to wring musical beauty out of such ugly subject matter as addiction and depression – things Smith, born on August 6, 1969, wrestled with until his tragic death, at the age of 34, on October 21, 2003. It’s easy to form a personal relationship with Smith’s songs, and that’s precisely why it’s so hard to rank them. In fact, we wouldn’t be surprised at all if your selection of the best Elliott Smith songs was different from our own.
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The planned title track to Either/Or didn’t actually make the cut for the album, though it’s stronger than some of the songs that did. It does, however, appear on New Moon, a collection of outtakes from the mid-90s that’s as essential as any of Smith’s studio albums. Like the Søren Kierkegaard text from which the song takes its name, Smith’s lyrics wrestle with futility – in this case, the futility of dealing with someone who doesn’t know what they’re talking about. “We’re all in the downpour you carry around for/Trashing a lifestyle you’ve never known,” he sings.
19: Son Of Sam
Figure 8 may be Smith’s toughest album: noisy and cluttered where its predecessors were hushed and spare. Different from its predecessors, it needs to be met on its own terms. But there’s no question that Smith’s newfound love of power-pop and electric guitar did nothing to dampen his knack for catchy melodies, as “Son Of Sam” demonstrates.
18: True Love
This long-unreleased song, which finally saw the light of day on the Heaven Adores You soundtrack, isn’t as breezy as the title would have you think. You don’t have to listen too closely to lyrics such as “So I bought mine off the street” and “All I need is a safe place to bleed” to get the sense that Smith isn’t really singing about love, but a very different kind of drug. But, oh how heart-wrenchingly beautiful this song is – as light as a balloon on a breeze.
17: King’s Crossing
“King’s Crossing” sounds like a nervous breakdown. Smith’s lyrics take us inside his tortured mind, where he wrestles with his worsening heroin addiction and paranoia about the music industry. That turmoil is reflected in the music, which folds in ghostly backing vocals, hypnotic pianos and queasy guitars. It’s one of Smith’s most unsettling songs and certainly, among his most ambitious, making you wonder what From A Basement On The Hill would have sounded like had Smith been alive to finish it.
16: Tomorrow Tomorrow
While Smith’s reputation as a brilliant lyricist is well documented, it also bears repeating that he was a phenomenal guitarist, and “Tomorrow Tomorrow” features arguably his most arresting, intricate performance. Like Richard Thompson’s “1952 Vincent Black Lightning,” it’s the kind of song that makes lesser guitarists want to tear their hair out in frustration and remains one of the best Elliott Smith songs.
15: I Figured You Out
“I Figured You Out” was to Smith what “Lift” was to Radiohead: a pop song that was just too perfect. Disowned by its creator (“Sounds like the f__kin’ Eagles,” he groused), given to friend Mary Lou Lord and then finally released on the 20th-anniversary expanded edition of Either/Or, “I Figured You Out” shows that, even before his major-label phase, Smith was finding ways to flesh out his lo-fi sound.
14: Sweet Adeline
Any worries that Smith had sold out by signing to DreamWorks Records for XO were eased by the album’s opener, “Sweet Adeline.” For about a minute and a half, it sounds like every other Smith song up until that point, only in higher fidelity – and then the chorus hits, delivering a rush of crashing drums and cascading pianos. Smith was still Smith, just with more at his disposal than ever before.
13: Somebody That I Used to Know
“I had tender feelings that you made hard/But it’s your heart, not mine, that’s scarred,” begins this kiss-off to a former flame (not to be confused with Gotye’s hit of the same name). He’s not bitter; just ready to move on. Figure 8 was a loud and at times overstuffed album, but some of the best Elliott Smith songs come from moments like this, when he pares things down to the bare necessities – just him and his guitar.
12: Waltz #1
Smith’s friends have said that “Waltz #1” was written after the songwriter listened to Elton John’s “Goodbye Yellow Brick Road” for 18 straight hours while high on mushrooms. The result may be Smith’s prettiest song. “Waltz #1” is seemingly untethered from conventional song structure and even gravity itself; it’s dreamlike and weightless, like a high you can’t come down from.
11: Can’t Make A Sound
Signing to a major label and working in a studio enabled Smith to record songs that he couldn’t have pulled off in a basement. Case in point: “Can’t Make A Sound,” a dizzying, Beatles-esque pop number that builds on its acoustic foundations into a thrilling climax, complete with strings and a blistering electric guitar. It’s a song that some critics likened to “A Day In The Life,” but even if it doesn’t get there, it gets far enough to leave you breathless.
10: Condor Ave
Less a song than a short story set to music, “Condor Ave” is one of Smith’s most vivid narratives. The narrator’s girlfriend drives off after an argument (“I threw the screen door like a bastard back and forth”); half-awake, she crashes into a drunk man along the road, killing them both (“I wish that car had never been discovered”). Legend has it that Smith was just 17 when he wrote this song, and he’d only get better.
9: Ballad Of Big Nothing
Let’s make something clear: “Ballad Of Big Nothing” is not a happy song, though it’s easy to mistake it for one, with its deceptively upbeat chorus (“You can do what you want to whenever you want to”) and punchy instrumentation. Had Smith written it a few years later, it might have had strings and a guitar solo. As it is, the song demonstrates how much he was able to do with so little, like so many of the best Elliott Smith songs.
8: Roman Candle
Opening Roman Candle, the album’s title track is quieter yet more abrasive than anything he’d recorded with his band Heatmiser. The threats in the chorus, “I want to hurt him/I want to give him pain,” are directed at his stepfather, who Smith claimed to have been abused by when he was younger. Listening to Smith’s voice, you can hear him tremble with barely suppressed rage.
7: Miss Misery
His most well-known song is also one of the best Elliott Smith songs. “Miss Misery” offers pop perfection in two forms: the downbeat early take included on New Moon and the fuller version heard in Good Will Hunting. Though the latter’s nomination for an Academy Award made a reluctant star out of Smith, it’s hard to think of a better song to bridge the gap between the two halves of his career.
6: Pretty (Ugly Before)
It’s tempting to take “Pretty (Ugly Before)’ at face value. The song itself is one of the most beautiful tunes Smith ever wrote. Lyrics like “There is no nighttime/It’s only a passing phase” could sound like an acknowledgment that even the worst of times will come to an end but, more likely, the song is referring to drug use, allowing Smith to stay awake for days and forget his troubles, at least until the high wears off.
5: Needle In The Hay
Unforgettably used to soundtrack a suicide attempt in The Royal Tenenbaums (arguably Wes Anderson’s most perfect use of music), “Needle In The Hay” is about a slower form of self-annihilation: heroin addiction. The song is Smith’s bleakest, and one of his simplest; he strums his guitar determinedly, like a writer driving his pen into paper, and sings like he’s struggling to get the words out. That’s all Smith needs to get under your skin.
4: Say Yes
Like the two tracks that follow on this list of the best Elliott Smith songs, “Say Yes” was one of three Either/Or highlights that also appeared in Good Will Hunting. Unlike the other two, “Say Yes” is an unabashed pop ditty – one of the sunniest that Smith ever recorded, even if it is a breakup song. “Situations get f__ked up and turned around sooner or later,” Smith sings, but, rather than staying down, he’s committed to standing up and moving forward.
While “Say Yes” is the song that concludes Either/Or, it’s “Angeles” that bids farewell to the first half of Smith’s career. Softly-sung vocals and fingerpicked acoustic guitar had been Smith’s modus operandi for a few years, and he’d continue to record songs this way for the rest of his life, but ‘Angeles’ feels like a peak. Adding to the song’s sense of finality are the lyrics, which read like an imagined dialogue between Smith and a dubious industry head. Sure enough, the follow-up to Either/Or would see Smith sign a new record deal and leave Portland for Los Angeles.
2: Between The Bars
It’s a testament to Smith’s songwriting mastery that “Between The Bars” sounds like a love song – which, in a twisted sense, it is, sung from alcohol to an alcoholic. Much has been made of how the “bars” of the title refer not just to taverns, but to the barrier that drinking forms between Smith and “the things you could do, you won’t but you might”. But the song also forms a barrier between the songwriter and who he once was, numbing himself to his traumatic past. With lyrics that are both comforting and controlling (“Drink up one more time and I’ll make you mine/Keep you apart, deep in my heart”) “Between The Bars” stands as one of the most devastating and best Elliott Smith songs.
1: Waltz #2 (XO)
The title of Either/Or, Smith’s finest album, suggested a dichotomy: Smith was either a lo-fi singer-songwriter or a composer of lush, orchestrated pop. “Waltz #2 (XO),” which heads this list of the best Elliott Smith songs, reminds us that he could be both at the same time. It’s such a light and gorgeous tune that you might miss the heaviness of the lyrics. The kiss and hug in the title is for Smith’s mother, whose marriage to Smith’s abusive stepfather fractured her relationship with her son. “I’m never going to know you now,” he laments in the chorus, only to walk that back with an even more heartbreaking promise: “But I’m going to love you anyhow.”