It’s almost impossible to listen to Elliott Smith’s music and not feel something. As amazing a songwriter as he was—one of the best to ever lay pen to paper or pick to string—more often than not, it’s his voice that does it. That soft, on-the-verge-of-breaking warble cuts to the core, crooning away about drugs, addiction, loneliness, betrayal, or missed connections. Elliott Smith was as painfully and tragically authentic as any artist over the last 30 years.
Born in Omaha, Nebraska, as Steven Paul Smith, the man who would rename himself Elliott bounced around the country in his youth before ending up at Hampshire College in Massachusetts. There he met Neil Gust and formed the indie alt-rock band Heatmiser. Soon after graduating, the two moved across the country to Portland, Oregon, recording three albums and two EPs before disbanding in the fall of 1996.
While still a member of Heatmiser, Smith began recording a batch of demos that his girlfriend convinced him to send to Cavity Search Records. The label immediately released them as Roman Candle, the singer’s first solo album, in 1994. The rough nature of the project is clear—four of the songs are titled “No Name.” Still, Smith’s affecting voice, singular guitar, and gift for creating simple but infectious melodies struck a chord in the underground scene. He was quickly snatched up by Olympia, Washington-based indie label Kill Rock Stars as a solo artist.
A self-titled record followed in 1995, and career highpoint Either/Or two years later. At the time, Smith was just another critically lauded singer-songwriter with a small but dedicated fan base. That all changed dramatically with the arrival of the film Good Will Hunting, as director Gus Van Sant tapped Smith to provide some music for the movie. Smith gave the director some songs from his last two records, as well as a freshly penned track, “Miss Misery.” When the film succeeded beyond reasonable expectation, Smith was honored with an Academy Award nomination for the song in 1998. He lost to Celine Dion and the juggernaut that was Titanic, but at long last, the world got a real look at what Elliott Smith was all about.
A major label contract with DreamWorks Records followed, as did the more ornately orchestrated albums XO and Figure 8. Smith, who had battled depression throughout most of his life, had never seemed happier to both friends and outsiders…until suddenly he didn’t. His drug addictions resurfaced, and his behavior grew erratic. In 2002, he entered a treatment facility to get clean, and seemed to be getting back on the right track while working on a new record. Everything took a sudden and tragic turn when, on October 21, 2003, after a fight with his girlfriend Jennifer Chiba, Smith stabbed himself in the chest twice, committing suicide.
A great deal of hindsight about Smith is based on the way he died. He’s generally viewed as a morose sad sack, pining and aching his life away, filling his songs with an overwrought degree of melancholy. Granted, many of the songs on the list below could send the listener running to a box of tissues faster than they can say “Needle In The Hay,” but there’s also a great deal of humor and positivity as well. Music is where Smith subdued most of the demons that plagued the interior monologue he could never overcome.
1. “Waltz #2” (1998)
This actually is a waltz, structured in the classic 1-2-3 rhythm conducive to that staid tradition of dancing. As a pop song, it’s an interesting form to build around, and shows off a level of sophistication coming from a musician many assumed was just another guy on guitar. “Waltz #2” is about a man going out for a night of karaoke, who then spots his mother out with her new husband for the first time, and all the internal turmoil and anger that transpires. Much like the rest of the songs on this playlist, it’s deeply personal and glaringly reflective of Smith’s own life experience.
2. “Between The Bars” (1997)
One of Smith’s more despondent songs, “Between The Bars” is a straightforward minor-key guitar ballad. Most of the drama is derived from the nearly whispered, pleading vocal delivery that drives the message home. It’s a song about addiction to alcohol, and the interesting perspective comes from the bottle itself, in its attempt to trick the object of its desire to “drink up one more time.” The bottle puts the drinker down—“People you’ve been before / They don’t want you around anymore”—only to position itself as the sole comforting force in the universe: “That push and shove and won’t bend to your will / I’ll keep them still.” It’s devastating.
3. “Son Of Sam” (2000)
Although named after the notorious New York serial killer, this second single off Figure 8 is difficult to decipher. Smith called it “an impressionistic song about destruction and creativity.” There are references to Shiva the destroyer, talking in your sleep, and telling off your boss. What makes the song enchanting is the instrumentation, like the early interplay between a jaunty standup piano and electric guitar. Things kick up a notch later when Smith stomps down on a fuzz pedal and explodes out with an equally overblown and melodic solo. It’s a hallmark track of his later major-label period.
4. “Angeles” (1997)
The first Good Will Hunting entry on the list, this song scores the scene when Matt Damon refuses to return Minnie Driver’s declaration of love, so it doesn’t carry the most upbeat feeling in the world. Beyond its downer tone, it ends up as an appropriate track for that particular moment. The song constitutes Smith putting into melody his own fears about making the move from Portland to L.A. and potentially signing with a major label. Everything that could go wrong is laid on the table, but much like Will Hunting, he inevitably takes the leap of faith. “So glad to meet you, Angeles.”
5. “Alameda” (1997)
Self-imposed isolation is a recurring theme in many of Elliott Smith’s songs, but he drives it home hardest on “Alameda,” named after a suburban street in Portland. Perhaps Smith was using the song to dress himself down for refusing to let people get too close to him, especially romantically. The chorus, repeated in the song’s extended coda, drives that point home: “For your own protection over their affection / Nobody broke your heart / You broke your own because you couldn’t finish what you start.”
6. “Say Yes” (1997)
“Say Yes” has a perverse twist ending: Opening with the lines, “I’m in love with the world / Through the eyes of a girl,” recited over an uplifting arrangement of major guitar chords, it seems like a run-of-the-mill saccharine pop ballad. The next stanza reveals the singer and his paramour broke up a month ago. The protagonist “feels like shit” and is left waiting and hoping that the person who left will take them back, still clinging to a false hope after getting dumped.
7. “Needle In The Hay” (1995)
This one isn’t hard to figure out: It’s all about heroin. Actually, it’s about a young heroin addict tagging along with an experienced one on their path to scoring another hit. It’s easily the most depressing song in Smith’s catalog, but also perhaps his most powerful. Foreshadowing Smith’s own end, this bleak song was used to score Richie Tenenbaum’s suicide attempt in The Royal Tenenbaums.
8. “Baby Britain” (1998)
We need to let a bit of light in after the heavy darkness of that last track, and “Baby Britain” is one of the few songs in Smith’s repertoire that sounds sufficiently jaunty and upbeat. Of course, being an Elliott Smith song, it’s really about a lonely alcoholic drinking the day away, staring into the ocean. But put that out of your brain and key in on the jangly piano and jazzy guitar instead. Lovely, right?
9. “Somebody That I Used To Know” (2000)
No, not the one-hit wonder Gotye song, this Figure 8 track finds Smith being unusually callous toward a former lover who left him with “tender feelings that you made hard.” Even when sung from the second person, most of Smith’s songs are directed toward himself, so it’s interesting to hear him go after another individual who left him hurting: “I know you don’t think you did me wrong / And I can’t stay this mad for long / Keeping ahold of what you just let go / You’re just somebody that I used to know.” This song also exhibits what an incredible guitarist Smith was, alternating fingerpicked arpeggios with up-tempo chord strumming, leading to an impressive acoustic solo tucked into the middle.
10. “Twilight” (2004)
One of Smith’s more sparsely orchestrated tracks, there’s not much beyond a few guitar chords, the sound of some crickets chirping in the distance, and a disparate string arrangement in the middle and the end to distract from Smith’s longing, lilting voice. “Twilight” is another song about addiction. It’s painful because it’s one of the few occasions where Smith recognizes that there’s an alternative—a great alternative, in fact—to a life of drugs, but he’s “already somebody’s baby.” A definite tearjerker, and the fact it was included on his posthumous record From A Basement On A Hill only makes it more so.
11. “Can’t Make A Sound” (2000)
Far and away his most bombastic and exhilarating song, this is Smith’s “A Day In The Life.” Beginning with a softly strummed intro, he reveals that he’s lately felt like a “silent movie,” but rather than just lay down and take it, he struggles. From there, the track progresses in movements with the cacophony building; at the two-minute mark it climaxes in a torrential wall of guitar that overwhelms any nuance and collapses like a tidal wave against your eardrum. It’s thrilling to hear him fight back, and the live version is spectacular in its own right.
12. “Thirteen” (2005)
Smith manages to make this Big Star classic his own. There’s a disarming and palpable shyness here that takes the place of the calm assuredness Alex Chilton brought to the original “Thirteen.” Smith recorded this cover for the soundtrack to the film Thumbsucker, as well as a take of the Cat Stevens track “Trouble.”
13. “Sweet Adeline” (1998)
This is a spectacular example of Smith’s mastery of dynamics and song construction. Opening with a simple descending guitar riff and a rather dry vocal, the track soon explodes into a brilliant Technicolor array of bashing cymbals and jaunty piano rolls. Where once Smith sounded like he was on the verge of nodding off, he explodes back to life; his voice is fleshed out, multi-tracked, and utterly brilliant.
14. “A Distorted Reality Is Now A Necessity To Be Free” (2004)
This is Elliott Smith sick and tired of “people raking in on the world.” As the title suggests, he feels a different view of things is the only way to free yourself from it all. In this song, Smith reveals he’s chosen to distort his own reality with myriad drugs, in this case heroin and LSD. It’s odd—and a little disturbing—to hear him sing with so much anger, especially at the song’s climax when he cries out with bewilderment, “God knows why my country don’t give a fuck.”
15. “Oh Well, Okay” (1998)
“Oh Well, Okay” is all about feigned indifference. It’s a lie, perpetrated out of emotional self-preservation. It’s the careless untruth we tell ourselves when people who used to mean a whole lot to us aren’t around anymore, and we convince ourselves everything is fine, or that they never mattered in the first place. And yet the narrator still clings to that box of “pictures, I just don’t see it anymore,” that they can’t bear to throw away. “Oh Well, Okay” is another example of Smith understanding what it means to deal with pain in the most relatable and unavoidably real way imaginable.
16. “Whatever (Folk Song In C)” (2007)
In this bittersweet song, the music is cheerful and somewhat uplifting as an incredulous Smith questions why a mysterious compadre refuses to leave his side, even after all of the drugs are gone. It’s an exaggerated, yet interesting glimpse into the way he felt that people viewed him, pondering why they would even want to be around him. Heartbreaking.
17. “Condor Ave.” (1994)
This track from Smith’s first solo album Roman Candle shows most of the hallmarks that would make him such a beloved figure in the indie rock music scene over the next decade. It’s a brilliant use of imagery—“the sound of the car driving off made me feel diseased”—delivered with a swirling multi-tracked vocal over a beautifully picked succession of notes from his guitar. It’s all the more amazing when you consider that this was basically a demo tape cleaned up and put through a quick mixing and mastering process.
18. “Miss Misery” (1998)
Saving the best, or at least the most well-recognized, for last. There’s a reason this song was nominated for an Oscar: It’s equally spellbinding and gut-wrenching. From the first line, “I’ll fake it through the day with some help / From Johnnie Walker Red,” you know you’re outside the confines of regular pop balladry. Thematically, “Miss Misery” is kind of a jumble, and its real charms stem from the imagery that Smith infuses the track with, like “A place I seen, in a magazine / That you left lying around.” It rides a fine balancing act between sweetness and melancholy, and the listener can’t help but hope that Smith will live up to the song’s promise to “come back when you want me to,” yet knowing it’s impossible.