The five saddest Elliott Smith songs
Few songwriters have been able to capture as much raw emotion in their recordings as Elliott Smith. Through a combination of multi-tracking, melancholic guitars and vulnerable vocals, he created a lo-fi sound that was just as intimate as the lyrics it would accompany, drawing listeners in with fuzzy warmth but always leaving them in a puddle of tears by the end of each song.
Smith’s sparse soundscapes were essential to his gloomy sound, but he really came into his own when he picked up a pen. From heartbreak to addiction to death, Smith consistently delved into the darkest corners of his mind for lyrical inspiration, turning them into poetry or simplifying them into devastating choruses. His songs have become a haven for those who relate to his feelings and his struggles with mental illness and substances.
Smith’s catalogue is filled to the brim with sad songs, each of them becoming all the more heartbreaking following his death in 2003. However, Smith’s influence cannot be understated. He has inspired countless other artists, from fellow indie folk songwriter Phoebe Bridgers to beloved rapper Frank Ocean, but he has also had an incomparable impact on his listeners, who turn to his songs for comfort and understanding, keeping his legacy alive in the process.
From his debut to his final album, Smith littered his releases with songs full of heartbreak and melancholy, and those you consider to be the saddest may depend on your personal relationship to them. Below, we’ve collated a list of five songs we consider to be the most heartbreaking compositions in Smith’s discography, ranging from his signature track ‘Between the Bars’ to the gloomy repetition of ‘Everything Means Nothing To Me’.
The five most heartbreaking Elliott Smith songs:
‘Between the Bars’
‘Between the Bars’ is the most well-known and well-loved song in Smith’s catalogue, and it’s easy to see why. The title alone shows off his talent with words, leaning into the main theme of alcoholism but also evoking musical language and prison imagery. In the song itself, Smith continues to use his skill with a pen to forge not just one of the most heartbreaking songs in his catalogue but one of the most heartbreaking songs of all time.
Smith embodies the false promises of drinking, urging his subject to “Drink up, baby, stay up all night with the things you could do, you won’t, but you might.” He sings of the potential that alcohol so often scuppers and of the pressure it offsets, the memories it keeps at bay. Fuzzy guitars enhance the lonely melancholy of his words, but, as usual, it’s Smith’s devastating lyricism that makes ‘Between the Bars’ so moving.
‘Waltz #2 (XO)’
‘Waltz #2 (XO)’ contains some of the most gut-wrenching lyrics in Smith’s discography. Who else could possibly craft a line as simple but steeped in vulnerability and heartache as, “I’m never gonna know you now, but I’m gonna love you anyhow.” The line could be applied to a number of situations, from a break-up to self-love, but Smith seems to be talking about his parents.
“XO, mom,” he sings later on in the song, “It’s okay, it’s alright, nothing’s wrong.” The instrumentation is slightly fuller than some of his more lo-fi offerings, with a piano line that sits somewhere between hopeful and haunting. As the soundscape swells around him, it only serves to intensify the emotions in his words, his struggles to know a loved one and his resolution to love them nonetheless.
‘Everything Means Nothing To Me’
The piano playing in ‘Everything Means Nothing To Me’, which is featured on Smith’s final album, Figure 8, starts out eerie and sparse. It works in tandem with Smith’s words, with his wonderings about the future and his picture in the paper. But as the song reaches its climax, as Smith’s words devolve into repetitions of the title, the soundscape becomes something else entirely.
The lonely piano gives way to a crash of drums and a soaring chamberlin, the swelling instrumentation mirroring Smith’s rising emotions. Although he repeatedly declares that everything means nothing to him, the stirring music tells another story. And as the song reaches new heights with each nihilistic line, it’s difficult not to feel the emotions running through Smith’s mind as he sings.
‘Everything Reminds Me of Her’
There are few break-up songs more honest than ‘Everything Reminds Me Of Her’. The track appeared alongside ‘Everything Means Nothing To Me’ on Figure 8 in 2000 and charts Smith’s feelings following the end of a relationship, with shrugged apologies and stark admissions of pain. “If I seem a little out of it, sorry,” he sings, “But why should I lie? Everything reminds me of her.”
Smith also contends with the attitudes of those around him, their repeated sermons of, “Why are you staring into outer space crying? Just because you came across it and lost it.” But he refuses to back down on his heartache, resolving to repeat the line, “Everything reminds me of her.” It’s stark and unapologetic, perfectly encapsulating the inescapability of heartbreak, the flippant comments of those who don’t understand, and how much it hurts.
‘A Fond Farewell’
‘A Fond Farewell’ isn’t quite as melancholic as some of Smith’s other efforts instrumentally, adorning his voice with hopeful twangs and warm instrumentation. Lyrically, though, the song contains some of Smith’s greatest and most devastating work. “This is not my life, it’s just a fond farewell to a friend”, he sings in the chorus, “It’s not what I’m like, it’s just a fond farewell to a friend.”
In the verses, Smith sings of veins full of disappearing ink and vomiting in the kitchen sink, potent imagery that serves the sombre tone of the song. “A little less than a human being,” he sings in one verse, “A little less than a happy high, a little less than a suicide.” The song is perhaps more difficult to decipher than some of his more straightforward lyrics, which only makes it all the more devastating as you’re left to figure out his fond farewell.
