With each passing year since his tragic death in 2003, Elliott Smith’s stature has continued to grow. Thanks in part to the loving curation of the label Kill Rock Stars, a few interesting biographies, covers of his work by prominent artists and a stirring documentary Elliott Smith: Heaven Adores You, released last year, more and more sad souls have discovered Smith’s emotionally revealing music. But the main reason Smith has endured is because of his impeccable craftsmanship all across his catalog and extending deep into his archives of material unreleased in his lifetime.

Smith followed in the lineage of folk-ish singers like Harry Nilsson and Nick Drake by blending melodic sensibilities that bowed to the Beatles with lyrics that eschewed popular convention. Yet, like his British counterpart, Smith suffered often-debilitating addictions that yielded some of the most vulnerable music of the era, but also inconsistent live performances.

Over the course of his too-short career, Smith released five solo albums. This list also takes into consideration songs from his three posthumous releases, even though they may not have been fully completed. We should’ve had so much more from Smith but what we do have is more than enough to make him a permanent addition to the classics. And so, here are the 12 best songs by Elliott Smith.



Although some of the lyrics on this tune come across as overly idiomatic, nearly to the point of cliché (“I wouldn’t need a hero if I wasn’t such a zero”), the total package isn’t trite whatsoever. Marked by the minimal production elements of the self-titled album on which it appears, this character sketch of a “low-riding junkie girl” hits the mark with an alluring arpeggiated waltz feel and a swaying chorus that condemns the speaker to the same itinerant fate of the girlfriend he’s describing. The image of “empty envelopes from some other town” illuminates for a moment a squalid world that, somehow, we don’t want to leave.



Smith’s aesthetic is defined by the disorienting contrast between the sumptuous beauty of his harmonies and the devastating self-loathing of his lyrics. Instead of coming across as sad or angsty, his tunes transmit an intoxicating melancholy that oddly feels good in its poignancy. The unsparing closing track on his career apex X/O captures this tension perfectly. It’s a completely a cappella song in which he offers lines like, “There’s nothing here that you’ll miss / I can guarantee you this / just a cloud of smoke / trying to occupy space, / what a fucking joke.” The vocals capture a haunting sneer on his lip as he delivers carefully layered four-part harmonies recalling the Beatles’ “Because” but, where that song is about finding an expanded universe through love, “I Didn’t Understand” builds levels of harmonics only to mourn the loss of love in a universe shrinking down quickly to nothingness.



X/O is widely seen as the record on which Smith first realized his vision of a full-blown, out-of-the-basement pop album. And the disc’s most perfectly executed track—which demonstrating his mastery as a songwriter, composer, arranger and multi-instrumentalist—is “Waltz #2.” The song inverts typical dynamics by making the verses and bridge sound huge while minimizing the chorus, which focuses attention on the ambiguous refrain of “I’m never gonna know you now but I’m gonna love you anyhow.”



The posthumously released From a Basement on a Hill hinted at some new directions for Smith, including dashes of psychedelia and shoegaze amid his broadening pop canvas. This standout tune, however, is more in the vein of his mid-career masterpiece Either/Or, a gorgeous acoustic track anchored by a heartbreaking refrain, “I’m already somebody’s baby.” But even here in stripped-down mode we can hear the development of Smith’s composition skills: turn up the track loud enough to appreciate the textural electric guitar sounds that act almost like an emotive layer of synth and you’ll hear that despite diving back to his acoustic roots he was still pushing forward into an abbreviated electric future.



This song is notable for having the greatest guitar lead in Smith’s catalog—which opens the song and recurs throughout—an absolutely perfect melody enhanced by a singing tone and just a hint of twang. That lead alone makes this track essential but it gains added heft because of the horrible sense of prophecy and foreboding in a song that was only released after Smith’s death. The speaker in the lyrics is sometimes the one saying goodbye, sometimes the one who’s leaving but we ultimately sense that we the listeners are the ones bidding a “fond farewell to a friend who couldn’t get things right.” Who else other than Elliott Smith could turn a song including the line “vomiting in the kitchen sink” into the go-to need-a-good-cry tune?



The double-disc collection New Moon filled Smith’s fans with joy a few years after his death by proving that the troves of unreleased material he generated in his lifetime were at the same uniformly high level of quality as any of his released work. The discs are brimming with incredible songs that run from the lo-fi Roman Candle era straight through his Either/Or transitionary period. The song “Pretty Mary K,” which seems to be addressed to a woman we encounter in a few Smith songs of this phase, is a total stunner thanks to a sublime hurts-so-good chord progression that milks every seventh and every minor-to-major switch for maximum swoon effect. We see Mary K with “some sailor’s pay shoved down in her sock” and we feel his yearning in the poignancy of a melody that seems to avoid tonic resolution, keeping us in his brilliant world of pain.



“He’s wearing your clothes, head down to toes a reaction to you.” Welcome to Elliott Smith, the album and the person. The opening track off his breakthrough record is one of the quietest rock songs ever, a passive-aggressive classic that follows in the footsteps of Lou Reed’s heroin chronicles but adds a brutal subtext that hints at the disturbing motivations of the addict. In spite of being one of his most familiar songs, “Needle in the Hay” is remarkably strange. There’s the momentary drumming that comes from nowhere mid-song and then suddenly stops never to return. There’s the uncomfortably long down-stroke held on a single note at the end of the instrumental bridge. There’s the question of who’s being burned when Smith turns the “s” in “marks” into a sharp hiss. But listeners know one thing for sure: “You oughta be proud I’m getting good marks” is one of the saddest statements Smith ever made, turning the needle tracks on his arm into a sick joke meant to reject anyone who would try to help him.



“Next door the TV’s flashing blue frames on the wall, / It’s a comedy from ‘70s with a lead no one recalls.” That line doesn’t appear in the Oscar-nominated version of “Miss Misery” that made Elliott Smith—seen performing the song at the 1998 Oscar’s ceremony decked out in an all-white Mark Twain suit—a household name briefly toward the end of his career. We had to wait until the posthumous New Moon to hear this slightly superior “Early Version” that has the same memorable hook but with a different set of disquieting lyrics telling a tale of a man who buys “two tickets” for a “place I’ve seen in a magazine that you left lying around” only to tear the tickets up and resume his endless late-night wandering. Maybe Smith sees himself in that “comedy from the ‘70s,” but years after his death we not only recall him but we hold him in an even higher regard than the film whose soundtrack introduced him to a huge new audience in the first place.



We remember Smith as a lyricist and a visionary, but we should never forget that he was also a phenomenal guitar player. He had a knack for creating finger-picking patterns that are both rhythmic and melodic, alternating the melody between the low-end with his thumb and the upper registers with his pinky finger. This track has one of his best guitar parts. And, appearing early in X/O, “Tomorrow Tomorrow” announces just how much Smith has mastered his career-long fascination with layered vocals, both doubled and harmonized. His voice alternates between a single pitch and a dense weave of harmonies in a hypnotic flow. Characteristically, the prettier the sounds the more self-loathing the lyrics; this track includes some of his sharpest insults directed toward a “he” and a “you” that he can’t quite bring himself to call “I.”



This legendary song from his greatest album, Either/Or brilliantly explores the double meaning of the word “bars” to convey both night life and prison, while painting a vivid scene in which the speaker gradually talks a lover into joining him for one drink too many. “The people that you’ve been before that you don’t want around anymore” will be driven away maybe by booze, maybe by romance. But what if the only way to be freed from your former selves is to be transferred to another jail?



We don’t usually hear Elliott Smith’s music referred to as emo, despite his fellow travellers’ fascination with depression, confession and death. Maybe it’s because Smith’s emotions are so complicated by beauty and pop trappings that Jawbreaker just doesn’t really jump to mind. But if there’s any song in Smith’s catalog that deserves to be viewed through this lens, it’s this knockout on From a Basement on a Hill. A song of almost tactile beauty, “Pretty (Ugly Before)” lays the hurt on thick with immensely vulnerable lyrics and a shimmering interplay of guitar and piano lines. The little keyboard lick that functions as a tag on the end of each chorus recalls Bruce Hornsby or The Band while the magnificent guitar lead boldly recalls George Harrison’s inimitable style and tone. No other song released after Smith’s death is more crushing: here is all his talent, his craftsmanship, his power on display in transition to a glorious new phase that was never meant to be.



This is just one of those cases where an artist’s signature song happens to be his best song, too. “Angeles” is the ultimate Elliott Smith song—a mini-masterpiece that captures the many facets of his brilliance. It has the iconic finger-picked acoustic guitar arrangement, a lyrical landscape that fashions a three-dimensional scene that’s both figurative and metaphorical, and a whispered vocal performance that hits harder than the loudest screaming ever could. This tale of being seduced back into gambling by a charming con man reverberates with meaning as it plays over and over in the listener’s mind. In textbook Smith form, the complex, conflicted melody seduces our inner ear as perniciously as the song’s addict is seduced back into his unholy game of cards.