Putting together a list of the best Elliott Smith songs is difficult for a couple of reasons. First of all, Elliott is not the kind of artist with a few big hits and a bunch of throwaways and filler. Ask 50 Elliott Smith fans what their favorite Elliott song is and you won’t get much overlap in responses. The second reason this list was so hard to put together is that going through 50 Elliott Smith songs will leave even the most cheerful of people in a slump of depression.

It’s been almost nine years since Elliott committed suicide, and time has only proven what we already knew: Elliott Smith was a one-of-a-kind artist. From the lo-fi acoustic style of his early days to the lush arrangements of his later albums, his music was crafted with precision and an attention to melody that rivals (gasp) The Beatles. But there was a recklessness about Elliott that separates him from other singer/songwriters and bands with a knack for catchy tunes. Brutally honest lyrics about drug use, alcohol, and emotional issues bleed through Elliott’s work and even at his most gentle and poetic, there’s a punk rock ethos that adds a layer of complexity to his entire body of work.

Nobody has filled the void left by Elliott. Most likely, it will be avoid that exists forever when somebody entirely unique comes along and leaves. Luckily, he’s left us with plenty to remember him by. Here are The 50 Best Elliott Smith songs.

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50. Elliott Smith – “Everything Means Nothing To Me” (2000)

Album: Figure 8

Possibly Elliott’s most dramatic song, “Everything Means Nothing To Me” opens the curtains with the confident keys of a grand piano and builds with angelic layers of vocals before breaking with an unexpected Phil Collins “In The Air Tonight” style drum climax. Not your typical Elliott Smith track, but here’s a glimpse into the depth of his musical capabilities.

49. Elliott Smith – “Pretty (Ugly Before)” (2004)

Album: From A Basement On The Hill

Another one of Elliott’s fully-realized songs off the posthumous From A Basement On A Hill, “Pretty (Ugly Before)” could be a fucking Tom Petty song musically, but Elliott’s exposed cracks and lyrical introspection put a different spin on things. It lacks some of the charm of his more raw material, but it gives a glimpse at the growth that Elliott may have shown if he remained on the path of continually more polished music.

48. Elliott Smith – “Good To Go” (1995)

Album: Elliott Smith

A standout from his self-titled album. “Good To Go” is a frequent Elliott expression that’s synonymous with “prepared to die.” The song is about meeting “a low riding junkie girl” who gets Elliott hooked on junk and leaves town just as quickly. “You can do it if you want to be like me.”

47. Elliott Smith – “A Passing Feeling” (2004)

Album: From A Basement On The Hill

Elliott’s music, although saturated with a post-1990 attitude, often borrows from classic rock as much as anything else. His influences run deep, and on songs like “A Passing Feeling,” those influences rear their heads. Tune in for the guitar solo in the end and you can hear the distinct classic rock feel that gives some of Elliott’s music a timeless feel.

46. Elliott Smith – “Clementine” (1995)

Album: Elliott Smith

One of Elliott’s standard, dark acoustic tracks, “Clementine” has a lo-fi, unfinished feeling to it. For some, it leaves a lot to be desired. To others, that’s part of the beauty of it. Songs like this aren’t meant to be dressed up and cleaned to a shiny finish.

45. Elliott Smith – “Independence Day” (1998)

Album: XO

Like “Baby Britain,” “Independence Day” has a bounce to it. For an Elliott Smith song, that immediately distinguishes it from the majority of his work. It almost sounds upbeat, but there a bittersweet element to the song, both lyrically and sonically, that give it depth.

44. Elliott Smith – “Placeholder” (2007)

Album: New Moon

Up until New Moon, Elliott’s music was becoming progressively more produced and fine-tuned. Whether that was a good or bad thing all depends on opinion. With New Moon, fans got to hear unreleased material from Elliott, recorded in the mid-’90s and returning to that stripped down, raw sound of his earlier projects. For the first time in years, we got a taste of the old Elliott with understated songs like “Placeholder.”

43. Elliott Smith – “Some Song” (1998)

Album: A Brief History

“Some Song” is an underrated song of Elliott Smith’s that people tend to leave out of the discussion. The lyrics, “you’re a symphony man with one fucking note” showcase Smith’s incredibly poetic but still unrefined side. Smith had a gift of saying so much with such few words, and the lyrics to “Some Song” exemplify that talent.

Elliott Smith – Some Song Lyrics

42. Elliott Smith – “Trouble” (2004)

Album: From A Basement On The Hill II

Elliott Smith’s cover of Cat Stevens/Yusef Islam’s “Trouble” appears on the soundtrack for 2005’s indie comedy “Thumbsucker.” It’s easily one of the best covers he recorded and could very well be the last track he ever cut.

41. Elliott Smith – “Big Decision” (2007)

Album: New Moon

“Big Decision” was another unreleased track recorded in Elliott’s Either/Or days and released after his death at 2007. The song has a frantic tone, and seems to be pretty clearly about not being ready to quit drugs. It’s not easy to listen to in retrospect, but it’s part of his story, and it’s a part that he clearly wanted to share.

40. Elliott Smith – “Pretty Mary K” (2000)

Album: Figure 8

Playing this song to any girl named Mary Kelly may be a surefire way to score, but the lyrics are particularly heartbreaking, even for our Elliott. “Gonna go down in the water, fill my mouth up full of sand/I’ll be waiting, still impatient, with my dead imagination while you’re with some other man” stings just to type or read, but his delivery of the couplet is all the more touching.

39. Elliott Smith – “I Don’t Think I’m Ever Gonna Figure It Out” (1996)

Album: Speed Trials Single

This short b-side is another example of Elliott plucking away at some pretty little tune that could have easily been about love, a day at the beach, or a picnic. The contrast between the sound and the content is, as usual with Elliott, heartbreaking.

38. Elliott Smith – “L.A.” (2000)

Album: Figure 8

One of Smith’s more upbeat rock’n’roll songs. This is the one you can play for your Incubus-loving friends. The lyrics are a sharp juxtaposition of the “cars parked in the sun/living in the day” of his Los Angeles surroundings and the dark “last night I was about to throw it all away” recesses of his mind.

37. Elliott Smith – “Bottle Up and Explode!” (1998)

Album: XO

XO was a departure from Either/Or, and had Elliott flexing his skills for more layered arrangements that we’d see him build on later in his career. For those looking for something in between the no frills style of his early work and the more complicated later songs, “Bottle Up and Explode!” is the perfect balance.

Elliott Smith – Bottle Up and Explode! Lyrics

36. Elliott Smith – “New Disaster” (2007)

Album: New Moon

This one wouldn’t have sounded a bit out of place on Either/Or. At some point in writing this list, it gets tempting to overuse words like “heartbreaking.” But when Elliott sings, “Your smile is just a ghost,” how else do you describe that?

35. Elliott Smith – “Pitseleh” (1998)

Album: XO

“Pitseleh” is a yiddish word for “little one.” As with all Elliott lyrics, there’s a lot to read into, but perhaps the main emphasis of this song is about breaking up with a girl you love because you know you’ll hurt her one day. “The first time I saw you/I knew it would never last/I’m not half what I wish I was/I’m so angry/I don’t think it’ll ever pass/And I was bad news for you/just because I never meant to hurt you.”

34. Elliott Smith – “Happiness” (2000)

Album: Figure 8

The irony of an Elliott Smith song entitled “Happiness” is unlikely to be lost on even the most casual of listeners, but the song does prove to be one of his more upbeat, at least melodically. The lyrics, of course, depict figures embroiled in personal turmoil, highlighting Smith’s ability to craft characters that seem at once general and too personal to be mere caricature.

Elliott Smith – Happiness Lyrics

33. Elliott Smith – “Twilight” (2004)

Album: From A Basement On The Hill

True to its name, “Twilight” echoes the dying of the light, a gorgeous, stripped down arrangement that blends Smith’s trademark acoustic guitar with the tasteful strings he often employed to tremendous emotional effect. The melody and instrumental choices highlight the tragic futility expressed in Smith’s lyrics, as the singer alternates the line “I’m already somebody’s baby” and “you’re already somebody’s baby.” A devastating vision of stilted love and addiction.

32. Elliott Smith – “Suicide Machine” (1997)

Album: Unreleased

Given Elliott’s suicide, this song is disturbing for its title alone. Even more disturbing is the (possibly untrue) rumor that it was recorded the day before he killed himself and his family refused to release it for years. As unsettling as that may be, it represents a part of what we’ll always love about Elliott Smith — the man didn’t sugar coat anything. He doesn’t tip-toe around the difficult stuff, and while his brutal honesty and striking fragility aren’t easy to stomach, they captured a part of the human experience that is often left in the dark.

31. Elliott Smith – “Rose Parade” (1997)

Album: Either/Or

“Rose Parade” is another one of Elliott’s songs that is pretty neutral in tone, and then you get into the lyrics. “When they clean the street, I’ll be the only shit that’s left behind,” Elliott sings towards the end, turning a pretty, melodically sound song into cracked porcelain.

30. Elliott Smith – “Memory Lane” (2004)

Album: From A Basement On The Hill

If not for the signature Elliott lyrics, “Memory Lane” could pass for a sweet, to-the-point little tune about the pastoral life. It’s not that. The song carries the weight of Elliott’s woes, but it does so with an almost sarcastic tone thanks to that light, hummable melody.

29. Elliott Smith – “Georgia, Georgia” (2007)

Album: New Moon

In under two minutes, Elliott crafts a letter of loss accompanied by chords that hint at the music of the state that lends its name to “Georgia, Georgia.”

28. Elliott Smith – “New Monkey” (2007)

Album: New Moon

“Pictures of hope (and depression)”–a lyric that perfectly encapsulates the sound of “New Monkey,” a song that cloaks its investigation of addiction with an uptempo, straight-ahead rock arrangement. As always, Smith’s silver lining is caked with rust: “anything is better than nothing.”

27. Elliott Smith – “Ballad Of Big Nothing” (1997)

Album: Either/Or

“You can do what you want to whenever you want to.” It sounds so hedonistic, so carefree. Leave it up to Elliott to give it a bittersweet, almost hopeless/reckless disregard.

26. Elliott Smith – “King’s Crossing” (2004)

Album: From A Basement On The Hill

Rising out of an ether of murmurs and distortion, “King’s Crossing” offers a striking blend of electronics and organics, heavily effected piano and haunting, wordless vocals forming a stunning minute and fifty-one seconds. Near the two minute mark, Elliott rings out crisply, before the track breaks into fall on wall of sound rock. The expert exploitation of dynamics and a wide sonic palette display the breadth of Smith’s toolkit on “King’s Crossing”–to say nothing of a song densely packed with some of the singer’s most arresting, bleak lyrics (“I took my own insides out/ it don’t matter ‘cuz I have no sex life/ And all I want to do now is inject my ex-wife”).

Elliott Smith – King’s Crossing Lyrics

25. Elliott Smith – “A Fond Farewell” (2004)

Album: From A Basement On The Hill

With its striking opening and eerie lyrics, “A Fond Farewell” serves as a sterling example of Elliott’s mastery of sorrow. A cryptic chorus and verses that run through characters that seem at once simulacra for Smith and, perhaps, other tragic figures he encountered–as he says, “this is not my life/ it’s just a fond farewell to a friend”–“A Fond Farewell” conjures the delicate balancing act of a life lived on the razor’s edge.

24. Elliott Smith – “Let’s Get Lost” (2004)

Album: From A Basement On The Hill

From A Basement On The Hill featured a lot of Elliott’s most fully realized songs. “Let’s Get Lost” kept things simple, recalling his earlier work with hushed vocals, acoustic guitar, and little else. It makes the lyrics really stand out, which may be why this is probably one of his most quoted songs.

23. Elliott Smith – “Miss Misery” (1997)

Album: Good Will Hunting Soundtrack

Nominated for an Oscar for its appearance in Good Will Hunting, “Miss Misery” has become one of Elliott’s best known songs. Of course, it lost to “My Heart Will Go On,” but although never a fan-favorite, it is probably many listeners’ introduction to Elliott.

Elliott Smith – Miss Misery Lyrics

22. Elliott Smith – “Junk Bond Trader” (2000)

Album: Figure 8

Beginning with the baroque sound of a harpsichord and giving way to a grand arrangement encompassing Elliott’s rock leanings and flair for the theatrical, “Junk Bond Trader” exhibits the singer’s ability to craft intricate arrangements that never overwhelmed his aching voice or detailed lyrics.

21. Elliott Smith – “Strung Out Again” (2004)

Album: From A Basement On The Hill

Matching personal turmoil with a tumultuous arrangement that alternates between plodding verses and a raucous, unhinged chorus, “Strung Out Again” mimics the highs and lows familiar to a man struggling through drug addiction. “Strung Out Again” embodies Smith’s pain and frustration structurally and sonically, creating a compelling, frightening mirror for his ultimately tragic battle.

20. Elliott Smith – “Coming Up Roses” (1995)

Album: Elliott Smith

“Coming Up Roses” displays Elliot’s supreme knack for wrapping dark topics and images–“the moon is a sickle cell/ it’ll kill you in time”–in upbeat melodies, or melodies that fall just a few notches short of cheery. This sort of masking makes the singer’s lyrics that much more haunting, hiding personal horror in the plainclothes of disarming pop.

19. Elliott Smith – “Almost Over” (2007)

Album: New Moon

Even in his most subdued songs, there’s always an element of recklessness in Elliott’s music. No amount of Bob Dylan influence could take that away. On “Almost Over” Elliott embraces this aspect of his personality and explodes into a panicked, anxiety-filled chorus loaded with stress.

18. Elliott Smith – “Son Of Sam” (2000)

Album: Figure 8

Said Elliott in an interview about “Son of Sam”: “It’s not about the serial killer, I’m not sure exactly what it’s about because it’s just sort of like telling someone a dream you had last night. There are some destructive figures in it, ‘Son of Sam’, Shiva… but Shiva’s also associated with creativity… I’m not sure… it’s just an impressionistic song about destruction and creativity, I guess; if it’s about anything.”

17. Elliott Smith – “Either/Or” (2007)

Album: New Moon

Clocking in at under two minutes and thirty seconds, “Either/Or” packs a power that utterly disregards run time. With a clean organ line that suggests the altar at which Smith laid down his words for weary listeners and himself alike, “Either/Or” takes on an almost religious quality and adding increased weight to an acerbic evisceration of an unnamed “you.”

16. Elliott Smith – “Angel In The Snow” (2007)

Album: New Moon

Consisting of a mere 78 words–many of which are repeated–Smith shows the power of his lyrics through concision and preciseness. “Angel in the Snow” is descriptive and definite, providing a series of typically ghostly images that loom far larger than the measured set of words used to create them.

15. Elliott Smith – “Needle In The Hay” (1995)

Album: Elliott Smith

It’s hard to talk about Elliott Smith without talking about drugs. They played a big role in Elliott’s life and he didn’t shy away from opening up about drug use in his lyrics. “Needle In The Hay” is one of Smith’s bare-boned tracks that has come to define him, partly because it deals so straight-forwardly with drug use and partly because it epitomizes the acoustic, minimalist style that often has Elliott’s strengths—his voice and songwriting—come through strongest.

14. Elliott Smith – “Can’t Make A Sound” (2000)

Album: Figure 8

With its opening line, paints a perfect portrait, a prison walled in by sadness: “I have become a silent movie.” Displaying Smith’s range, “Can’t Make A Sound” starts simply with the singer accompanied solely by guitar, before building to its symphonic close–a coldly comforting coda that matches the depth of the song’s sadness with arresting grandeur powerful enough to defy its own title.

13. Elliott Smith – “Christian Brothers” (1995)

Album: Elliott Smith

Haunting and hard in equal measure, “Christian Brothers” sprawls trenchant lyrics across a melancholy melody. Smith’s voice, clear and pained as ever, cuts through a mix that on its own could evoke shreds of the coming nightmares the singer intones. Difficult, dark, and absolutely gorgeous.

12. Elliott Smith – “Baby Britain” (1998)

Album: XO

Wait, did Elliott write a song that you can be happy to? Well, content-wise, this one doesn’t spew rainbows and flash smiles, but the piano and Beatles-esque melody provides the lyrics in “Baby Britain” with some bounce in its step unlike any other Elliott song.

11. Elliott Smith – “Between The Bars” (1997)

Album: Either/Or

“Between The Bars” is the sweet Elliott we choose to remember – the Elliott who got a tattoo of his Munro Leaf’s “The Story Of Ferdinand” about a bull that loves to smell flowers.

Elliott Smith – Between The Bars Lyrics

10. Elliott Smith – “No Name No. 5” (1997)

Album: Either/Or

“No Name No. 5” finds our Elliott with “bitten fingernails and a head full of the past,” and therein contains a beautiful construction and progression. The best moment to start crying is when the drums kick in at 1:57.

9. Elliott Smith – “Southern Belle” (1995)

Album: Elliott Smith

“Southern Belle” has some of the most layered, intricate guitar work of Elliott’s entire catalogue. The song is supposedly about Elliott’s stepfather’s abusive relationship with his mother.

Elliott Smith – Southern Belle Lyrics

8. Elliott Smith – “Alameda” (1997)

Album: Either/Or

Either/Or is often considered Elliott’s best album, but it offers little insight into Smith’s talent for composition. With mostly raw, stripped down songs, we didn’t get to hear what Elliott would prove with his later work: he’s very good at arranging layers, complimentary elements, and full-bodied songs. “Alameda” was the most lush song on the album, even including some George Harrison-like guitar work that would come to be a familiar element on Elliott’s following albums.

7. Elliott Smith – “Everything Reminds Me Of Her” (2000)

Album: Figure 8

The most effective of Elliott Smith’s songs are the ones drenched in his own truths. He gets deeply personal, but some of his issues are so specific that the meaning is only true to him. On “Everything Reminds Me Of Her,” he tells a more universal story, painting a vague picture that also manages to be sharply vivid with lines like, “The spin of the Earth impaled the silhouette of the sun on the steeple.”

6. Elliott Smith – “Say Yes” (1997)

Album: Either/Or

Elliott called this song “insanely optimistic.” Okay, so it’s not a happy song, but there’s a feeling of hope that you don’t too often get with Elliott, and it makes “Say Yes” stand out from the majority of his bleak work.

Elliott Smith – Say Yes Lyrics

5. Elliott Smith – “Somebody That I Used To Know” (2000)

Album: Figure 8

Let’s all boycott Gotye’s “Somebody I Used To Know.” Nothing against Gotye, but when you go through a break-up and the closest person in your life fades away into another stranger, it certainly feels more like Elliott’s song than it does Gotye’s.

4. Elliott Smith – “The Biggest Lie” (1995)

Album: Elliott Smith

Elliott’s second album is one filled with pain and desperation. It’s clearly the work of a man gripped by depression, drug abuse, and internal struggle. But even among songs like the trademark “Needle In The Hay,” “The Biggest Lie” finishes the album on it’s most moving note and is quite possibly Elliott’s most humanly painful and impossibly gorgeous songs.

Elliott Smith – Needle In The Hay Lyrics

3. Elliott Smith – “Angeles” (1997)

Album: Either/Or

“Angeles” is a beautiful song perhaps best known for appearing on both the Good Will Hunting and Girl Next Door soundtracks. The layered acoustic guitars and whispered vocals are what makes the song so beautiful. This is one of the first of many Elliott songs written about his relationship with Los Angeles. The lyrics are pointedly about the industry of disposable celebrities in LA/Hollywood. “Picking up the ticket shows there’s money to be made/go on and lose the gamble that’s the history of the trade/you add up all the cards left to play to zero and sign up with evil/Angeles.”

2. Elliott Smith – “Waltz #2 (XO)” (1998)

Album: XO

On “Waltz #2,” Elliott Smith sings a heartbreaking, poetic tune about his mother, but more than the content, it’s the feelings evoked by the song that make it so powerful. As hard as Elliott’s music can be to listen to, the beauty in songs like this make the listening experience worth it.

Elliott Smith – Waltz #2 Lyrics

1. Elliott Smith – “2:45 A.M.” (1997)

Album: Either/Or

“2:45” A.M. doesn’t feel like a complete song. It builds tension until 2:30 in, when it finally breaks, only to start fading out at 3:00. It leaves you with a feeling of slight disappointment, and it leaves a lot to be desired. And then you think about the title, and then you think about what the song means, and then you think about Elliott Smith’s career. And suddenly, it not only makes sense—it’s perfect.