Kettering — The Antlers (2009)
One of multiple Antlers entries on this list, “Kettering” is the first full-length track from the 2009 “masterpiece of sad”, Hospice. “Kettering” nails every aspect of the staple, sad song: a slow tempo with haunting chords, barely audible vocals and unnecessarily depressing lyrics. The only real knock against “Kettering” on this list is that it’s not even the saddest song from Hospice – an album that Pitchfork lauded for its “power to emotionally destroy listeners.”
I Can Feel Your Pain — Manchester Orchestra (2007)
Unlike The Antlers, Manchester Orchestra makes music that is not quite as singularly emotional (meaning they have reasonably good happy songs too). Nonetheless, Andy Hull and the boys are also top-notch when it comes to making depressing music. Don’t confuse the empathetic nature of the title with optimism – it is still disheartening and emotionally encumbering. All in all, quite a fitting song for an album titled “I’m Like a Virgin Losing a Child” (yikes).
First Day of My Life — Bright Eyes (2005)
When it comes to sad music, Conor Oberst is the king. The fragility of Oberst’s voice is a bit worrying (I fear that he may crumble into dust at any second) but part of Bright Eyes’ success in the early aughts is that they simply make very relatable music. Case in point, “First Day of My Life” is the perfect musical expression of “dejection” and is one those songs that every single one of us, at one point in our lives, really needed to hear.
Flesh and Bone — Keaton Henson (2010)
Another one of the great masters of sad music, Keaton Henson has a gift of making quiet, unassuming songs that are also still totally consuming. Like Oberst, Henson’s weak, tired voice makes it sound like he might literally die (something that seems to be supported by the lyrics), but it is also an essential component of what makes Keaton Henson the artist he is, and what makes “Flesh and Bone” such a deeply emotional song.
To Build a Home — The Cinematic Orchestra (2007)
In some ways, this song is polar opposites with “Flesh and Bone”. Although both songs have a solemnity to them, “To Build a Home” has more of a bittersweet feel that seems to even suggest a sense of awe at all the beautiful things in the world. Perhaps this is due to the absolutely magnificent vocals of Patrick Watson, one of the most underrated vocalists in indie rock. This is one of Watson’s personal career highlights and easily the best song The Cinematic Orchestra has ever made.
Skinny Love — Birdy (2011)
This cover of a Bon Iver classic launched Birdy’s career at the young age of 15. A stunning rendition, “Skinny Love” perfectly captures the sentiment of the original while also presenting it in a new skin. As for the meaning of the title, from Justin Vernon himself: “[if] you’re in a relationship because you need help… that’s not necessarily why you should be in a relationship… that’s skinny. It doesn’t have weight. Skinny love doesn’t have a chance because it’s not nourished.”
Hero — Regina Spektor (2006)
Possibly one the most underrated decisions in filmography in the last ten years was the decision to pair this song with the “Expectations versus Reality” scene from 500 Days of Summer. Spektor’s vocals here are as stunning as always, and though there are few lyrics in this song, they are striking and thought-provoking. Amazingly, “Hero” was originally released only as a bonus track before it was featured in the “500 Days” soundtrack.
Your Ex-Lover is Dead — Stars (2004)
This is one of my favorite songs of all-time (even transcending emotional category!). “Your Ex-Lover is Dead” tells the story about two former lovers crossing paths years after their relationship dissolves, which is cool and all but I find myself more impressed by the music than the lyrics here. The song is perfectly paced and constructed but also incorporates the use of classical instruments with indie rock to its maximum potential (something that Stars happens to be very good at).
Thirteen — Ben Kweller (2006)
A short and sweet song that Kweller released before he evolved into a terrible country act. As this is a stripped down song of just voice and piano (and harmonica), I like to believe that it reflects an earlier period of innocence and young love (perhaps at age thirteen – strong deductive skills on my part, I know).
Small Hands — Keaton Henson (2010)
Another sad Keaton Henson song and another sad classic. Never have I felt such a strong emotional connection with what someone has to say about another person with small hands. While a bit faster paced than other Keaton Henson songs, “Small Hands” is no campfire sing-along – unless everyone at this campfire is okay with having all of their hearts musically broken.
Sway — Voxtrot (2006)
I tried really hard to get Voxtrot on this list because they have an Indian vocalist and I love that. Sadly, while Voxtrot did not last long as a band (releasing just one full-length album), they managed to put out many great tracks featuring a sad-sounding vocalist and wonderful stringed instruments. This is one of those tracks.
Bear — The Antlers (2009)
“Bear” is the most deceptively sad song off the saddest album I know (the aforementioned Hospice). Its faster tempo (in some places) and innocent-sounding, lullaby-based melody makes it seem almost like a cheery intermission from the rest of the thoroughly depressing album. Instead, a closer listen to the lyrics reveals that is a sad tale of an unplanned pregnancy and secret abortion.
Starálfur — Sigur Rós (1999)
Despite the fact that this song is sung in Icelandic (as are all other SIgur Ros songs), Starálfur is an emotional experience to all who hear it. Somehow Sigur Rós has captured all of the emotions of all the wonderful moments in life – weddings, births, first love, etc.) and captured its essence in a song. The only thing that would ruin it is if its translated lyrics were actually nonsense…
Hurt — Nine Inch Nails (1994)
The final track of The Downward Spiral, a 1994 concept album describing a man’s “downward spiral” into madness with violence, drugs, sex and suicide, “Hurt” is a hard song to listen to – not only for its powerful lyrics, but because Trent Reznor added distortion noises to the song that literally made it hard to listen to. Johnny Cash made his own (very respectable) rendition of this song, but it’s hard to be as sad as Reznor can.
Street Spirit (Fade Out) — Radiohead (1995)
Thom Yorke had this to say about this song: “All of our saddest songs have somewhere in them at least a glimmer of resolve – ‘Street Spirit’ has no resolve. It is the dark tunnel without the light at the end. [Our Fans] don’t realize that ‘Street Spirit’ is about staring the f–king devil right in the eyes… and knowing, no matter what the hell you do, he’ll get the last laugh.”