Elliott Smith: Top 10 Songs, 10 Years Later

Elliott Smith
Elliott Smith

By Soheil Rezayazdi

If you’re reading this, it’s possible you remember October 21, 2003, like I do, as something of an emotional flashpoint. Elliott Smith fans felt his death with the effect of blunt-force trauma. We spent that fall in mourning for a man most of us had never met. We soaked in his music and read every last obit. We burrowed in message boards with likeminded fans. Our friends offered condolences as though a family member had died. We came to terms with a simple truth: For us, Elliott Smith occupied a space that no other musician could ever fill.

Ten years later, the songs have lost little of their power. This list attempts to capture what made that awkward man in the white suit so essential to so many. I’ve consulted his entire body of work here: album tracks, B-sides, unreleased recordings, and songs from his days in Heatmiser. Steven Paul (“Elliott”) Smith wrote unassuming little songs of profound impact to people like me. He would have turned 44 this August. Consider this list a celebration of the man and his work.

10. A Fond Farewell

Album: From a Basement on the Hill (2004)

Elliott had a fascination with hard drugs long before he became a user himself. By most accounts, those infamous early tracks like “Needle in the Hay” reflected an interest in dramatic storytelling, not a history of drug use. But things changed by the time he recorded “A Fond Farewell”. Here, Elliott sings deeply unsettling lines like “Veins full of disappearing ink/ Vomiting in the kitchen sink” in his signature nonchalant style. Elliott could explore the ghastliest subjects without a hint of histrionics. The lyrics suggest a recovering addict who, now clean, relapses in a moment of weakness. “This is not my life,” he pleads. “It’s just a fond farewell to a friend.” Anyone caught backsliding on a bad habit, I’m sure, can relate. “A Fond Farewell” ranks among Elliott’s most heartbreaking songs for, of all things, its inherent optimism. It did sound like Elliott was saying goodbye to heroin in 2003. He got clean, he did a few shows, and he began talks of an ambitious double album. But it didn’t work out that way. The fond farewell, it turned out, was to us.

09. Plainclothes Man

Album: Mic City Sons (1996)

Before Good Will Hunting turned him into an Oscar nominee and a film soundtrack staple – see: The Royal TenenbaumsAmerican BeautyThe Girl Next DoorKeeping the Faith – Elliott had released three records with Heatmiser, an emo-tinged grunge outfit out of Portland. Aggression and self-pity dominated the group’s first records. Elliott penned songs with names like “Bastard John” and “Busted Lip”, and he sang them like a man who’d screamed himself hoarse the night before. Mic City Sons, the group’s last album, eschewed the angst to offer a prologue to the sound that Elliott would soon master. Take “Plainclothes Man”, a song that could have easily camouflaged its way onto Elliott’s best solo records. An unabashed slice of college radio indie rock, “Plainclothes Man” finds Elliott exploring his key obsessions: alcoholism, his stepfather, and broken relationships. The song defies an easy reading, like most on this list, but Elliott peppers his musings with such memorable, concrete quips. The strong melodic hooks and lyrical abstractions are an early sign of Elliott as a maestro of melancholic pop.

08. Sweet Adeline

 Album: XO (1998)

“Sweet Adeline” is a sonic statement of purpose. The opener off Elliott’s XO, the song marks a clear dividing line between the man’s early, homemade records and his later, studio-centric sound. Hell, you can hear that shift in the song itself. “Sweet Adeline” begins very much in line with Elliott’s first records: a frail voice whispers ominous nothings over sparse acoustic guitars. And then, something strange happens: A light bulb flickers inside a dark room, revealing a trove of previously unseen treasures. That’s “Sweet Adeline”. For 90 seconds, Elliott teases us with his beloved sound, only to upend the track into an orchestral blast of chamber pop (a neat trick Sufjan Stevens would steal, to great effect, on the first two tracks off The Age of Adz). In interviews, Elliott expressed a desire to “kick the door open” with an opening salvo that let people know that “this was not an acoustic record.” Mission accomplished. Elliott set dynamite to the sound he’d spent three records perfecting, and he delivers one of the most hair-raising moments of his discography in the process.

07. A Distorted Reality Is Now a Necessity to Be Free

Album: “Pretty (Ugly Before)” B-side

Elliott fans waited three long years for new material after the release of Figure 8. Our dry spell ended in 2003 with “Pretty (Ugly Before)”, a rollicking single and the final release of Elliott’s life. The real revelation here, however, was the B-side: “A Distorted Reality Is Now a Necessity to Be Free”. The track finds Elliott adapting his low-fi sound into woozy psychedelic pop. After years of guitar-led balladry and power pop, this claustrophobic stoner dirge came as a total change-up in 2003. And yet, can you imagine a more seamless stylistic transition for Elliott Smith? “A Distorted Reality” still sounds like it could have been recorded in your bedroom. The whispered intimacy and warm melodies remain, as sturdy as ever. Elliott translated his signature elements into a foreboding, “I Am the Walrus”-like stomp. Heard in 2003, the song held enormous promise for Elliott’s new direction. Only Elliott would introduce a guitar hook as lovely and haunting as the one that emerges at the 2:26 mark, only to have the song fade out seconds later.

06. Between the Bars

Album: Either/Or (1997)

Which song of the last 20 years do you most wish you’d written? A journalist once asked Madonna this question. Her answer: “Between the Bars”, a two-minute ballad made famous as one of five Elliott songs featured in Good Will Hunting. “Between the Bars” lulls you like a good, stiff drink. Melodically, it really could pass as a lullaby. The phrase “drink up, baby,” repeated throughout, sounds like something you’d coo to an infant. But you’d have to be a serious lover of gallows humor to sing this song to a kid. “Between the Bars” is the sound of a late-night, moody drunk. Its lyrics, written from the perspective of alcohol itself, urge the listener to stay up all night and get quietly hammered. Here is the siren song of that bottle of whiskey next to your nightstand. “Between the Bars” coaxes you to resign from sobriety, to silence the memories and doubts that pollute your head. Elliott sings of “waiting to finally be caught,” expressing the thoughts of a fatalistic drunk playing with death. Defeat never sounded so beautiful.

05. Christian Brothers

Album: Elliott Smith (1995)

Where “Between the Bars” warms you like an old fashioned on a cold night, “Christian Brothers” sprays alcohol on a raging fire. Here’s the sound of an unqualified mean drunk. Named after a brand of bottom-shelf brandy, the song stands among Elliott’s angriest tracks. It’s certainly his most profane. Just listen to that vengeful opening couplet: “No bad dream fucker’s gonna boss me around/ Christian Brothers gonna take him down.” Early in his career, Elliott often sang of vague, violent memories from his youth. Fans have interpreted these lyrics as allusions to the alleged abuse he suffered from his stepfather. Regardless of its source, anger infused much of Elliott’s work, a fact lost on those who reduced his songs as “sad bastard” music. On “Christian Brothers”, the song’s protagonist celebrates the memory-erasing powers of cheap liquor. He knows the alcohol “won’t help me get over,” but that doesn’t stop him from opening another bottle. With its venomous lyrics and wonky guitar riff, “Christian Brothers” awaits a thunderous metal cover to do it justice.

04. Happiness

Album: Figure 8 (2000)

Even the sunniest songs in Elliott’s catalogue have a way of hinting at past trauma. Take “Happiness” and its closing refrain: “What I used to be will pass away and then you’ll see/ That all I want now is happiness for you and me.” It’s a lovely sentiment, one that often pops into my mind at the start of a new relationship. But what exactly did Elliott used to be? An alcoholic, an addict, a depressive, a victim of abuse? The song doesn’t say. But these words color the whole track; they turn a nurturing pop song into a eulogy for a past self. Elliott attacks his ailments from an oblique angle here. As a lyricist, he rarely reveled in on-the-nose misery. Elliott far preferred impressionistic turns of phrase, ones that conveyed a mood but didn’t read like emo diary entries. “Happiness” remains one of the best introductions to Elliott’s work (it served as my personal gateway into the cult of Elliott Smith). Its wistful versus, mid-tempo drive, and triumphant closing make for an ideal first impression.

03. Waltz #2

Album: XO (1998)

Elliott’s most straightforwardly beautiful song, “Waltz #2” is the one you play for your parents, your skeptic friends, your hardened holdouts. Prior to “Waltz #2”, Elliott had released records like Either/Or and Elliott Smith – gut-punch albums with nary a string or horn arrangement. “Waltz #2” showed us what a smart pop craftsman could do if given a studio and a budget. And yet, even with the strings and layered vocals, the song maintains the intimacy of Elliott’s first three records. Strip it of its flourishes, as he did live, and you’d have another piece of feather-light pop. The lyrics read like an abstract ode to Elliott’s mother and her relationship with Smith’s stepfather. Elliott speculates on his mother’s inner state (she “stares into space like a dead China doll”) and ends with an ambiguous kiss-off: “I’m never gonna know you now/ But I’m gonna love you anyhow.” Elliott rolls his complex feelings toward his mother into a single, lovely phrase. The line doubles as a sentiment shared by Elliott Smith fans the world over.

02. King’s Crossing

Album: From a Basement on the Hill (2004)

Elliott’s music took a sharp turn toward the psychedelic in the last years of his life. In his final interview, he alarmed fans of his vintage sound with statements like, “Lately I’ve just been making up a lot of noise.” Most of these late-era experiments have yet to see a proper release. The closest thing to “a lot of noise” on his posthumous album, From a Basement on the Hill, is “King’s Crossing”. The track opens with 100 seconds of pure auditory hallucination: a drunken poetry reading, distant laughter, sinister guitars, a heavenly piano riff.

“King’s Crossing” sounds like nothing Elliott ever released prior, but that fact alone doesn’t make it a high-water mark. The track is also among Elliott’s most propulsive, heartrending, and funny – not to mention experimental. True, lyrics like “Give me one good reason not to do it” send “King’s Crossing” down some truly dark rabbit holes. But the song has a real knack for the playful and absurd. Just listen to that wildly uncharacteristic beat-drop at the 2:23 mark or the cheeky way he alludes to drug use (“I’m going on a date with a rich white lady/ Ain’t life great?”). Elliott bared his soul on “King’s Crossing”, but he was also getting off on subverting our expectations of what an Elliott Smith song was supposed to sound like.

You can hear that newfound, fuck-it-all attitude all over Basement. “King’s Crossing” erupts from nowhere in Elliott’s catalogue, and it remains a sad sign of the musical vitality he still had in his final months.

01. The Biggest Lie

Album: Elliott Smith (1995)

Elliott Smith could make you feel like you weren’t alone. Sometimes, on those most transcendent songs, he sounded like he was right there in your bedroom. Of the more than 100 songs released under his name, none have that delicate, you-are-there intimacy quite like “The Biggest Lie”.

Elliott fans have long resented the idea that his music was just a soundtrack to your latest break-up. His songs contain multitudes, we’ve argued. We shouldn’t relegate him to the stuff of sad montages. Despite these truths, Elliott’s music does make for an ideal companion during your most vulnerable moments. He created emotional balm. His songs enable depression, sure, but they also enable catharsis. Something about these sketches of inner turmoil comforts us.

As such, “The Biggest Lie” soothes the soul even as it breaks your heart. Fans continue to debate the secrets hidden in these short versus. What, exactly, is the biggest lie? Is the one-way train an allusion to death, to heroin, or to nothing at all? Does the song’s subject “make everybody late” by jumping onto the tracks? The lyrics provide clues to some sort of tragedy – a broken relationship, debt, maybe drugs, maybe suicide – but Elliott refuses to craft a literal story with a beginning, middle, and end.

As he told Carson Daly in this seriously awkward TRL interview about “Miss Misery,” “I didn’t try to make [the song] into any sort of, like, weird narrative.” He rarely did. Elliott dealt in portraits, and they never came out so raw and simple as they do here. Lines like “I’m tired of dancing on a pot of gold flake paint” are the reason Elliott Smith super-fans still exist 10 years after his death. Elliott captured the allure of oblivion, the desire among depressives to simply feel nothing. And he did it with songs so delicate that a gust of wind could send them dissipating into the air.

“The Biggest Lie” is Elliott’s most fragile creation, and it’s a devastating snapshot of an artist in top form.