Elliott Smith left us way too soon, but he also left behind a treasure trove of music. No one could sink his teeth into a sad song in quite the same way, thanks to his way with a melody and his unique ability to turn a lyrical phrase.
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We could go much deeper with this list if we chose. But for now, here are five highlights from Smith’s career that demonstrate how he could devastate you with a weeper like few artists before or since.
“The Biggest Lie” from Elliott Smith (1995)
As Smith developed throughout his career, the production became more ornate and filled-out. But there’s something to be said about his early stuff, where he often accompanied himself with just an acoustic guitar. When he approached songs in that fashion, it really threw focus on the beauty of his melodies and the tremulous quality of his voice. On “The Biggest Lie,” the closing track from his self-titled sophomore solo album, all of those qualities come to the fore, and the effect is overwhelmingly sad and beautiful.
“Between the Bars” from Either/Or (1997)
Smith often utilized the waltz rhythm, realizing that there was something inherently sorrowful about the one-two-three, one-two-three of it all. In the case of “Between the Bars,” Smith uses it in the service of a character sketch, detailing the heartbreaking, alcohol-fueled deterioration of someone squandering their potential. But he doesn’t judge this person, realizing there are things beyond her control driving her to this behavior. The narrator seems to be the alcohol personified, promising to numb her demons.
“Miss Misery” from Good Will Hunting: Music from the Motion Picture (1997)
The song that put Smith on the map, although it was fair to wonder if he ever really wanted to be there. Let’s give credit to Ben Affleck and Matt Damon for realizing his talent when they heard it, as they exposed his music to a much wider audience in the process. Who could forget Smith performing this song on the Academy Awards, bringing such authenticity to a night so associated with artificial glitz? And, fittingly, he did so by delivering one of his trademark weepers, one about a guy clinging to a relationship that’s fading from him with every moment.
“I Didn’t Understand” from XO (1998)
The consensus is XO is Smith’s masterpiece, as he indulged in his Beatles fandom by amping up the swirling, circus-like production flourishes. “I Didn’t Understand” is his one-man version of the Fab Four’s harmony-drenched “Because.” By multitracking himself from every direction, he threw a spotlight on an underrated aspect of his allure, which was the naturally engaging quality in his vocals. The way the melody crawls almost menacingly in the verses before opening up into the gilded chorus just adds to the effect.
“Better Be Quiet Now” from Figure 8 (2000)
If anything, the flirtation with fame brought about by his Oscar appearance only seemed to make Smith even more downcast, at least if the musical evidence is to be trusted. Figure 8 continues in the baroque pop vein of XO, and it’s just one soul-crushing track after another. The sadness peaks on “Better Be Quiet Now,” which features some lovely, delicate guitar work from Smith. Meanwhile, the lyrics make an eloquent case that the old adage about it being better to have loved and lost than to have never loved at all is utter hogwash.
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