The 100 Saddest Songs Ever Made (#100–75)

I had the pleasure of living in the southern hemisphere from June to August of this year. It was a life changing, amazing experience. But it also meant that I went from Winter to Spring to Winter again. And as the cold rains of a Oregon winter march forward, I’m missing the sunshine. So what better way to celebrate (mourn?) with a list of the saddest songs I’ve ever listened to? After exhaustive research through Twitter, Facebook and my own back catalogue of music, these are the songs that crush me the most.

100.“Human Performance”- Parquet Courts

Professional slackers and pranksters Parquet Courts usually sing about being stoned, starving or making fun of Texas, but when they let their emotion really get into the music, it’s like a hurricane ripped through the studio. “Human Performance” might be the finest Velvet Underground song Lou Reed never penned, with novella worthy lyrics and a brilliantly echoy chorus painting a picture of desperation. “Busy apartment, no room for grieving/Sink full of dishes and no trouble believing, that you are leaving.”

99. “These Days”- St. Vincent

Did you know Jackson Browne wrote “These Days” at only 16? And that over a dozen artists have covered it? And that this version fucks me up every single time? The more you know.

98. “In the Wee Small Hours of the Morning”- Frank Sinatra

Just a year after In the Wee Small Hours, Sinatra would release the breezy Songs for Swinging Lovers, which has to be one of the strangest turnarounds in any artists’ discography. Because In the Wee Small Hours is the saddest damn jazz album ever made. “In the Wee Small Hours of the Morning” sets the stage for a full album of regrets, bad dreams and late nights splattered with rain. Or, as Sinatra puts it, “the time when you miss her most of all.”

97. “Oblivion”- David Bazan

I’ve seen David Bazan live three times now, and he’s pulled this crushing track out every time. It’s not just an amazing addition to the “sad touring songs” canon, but just a generally brutal song. That ghostly keyboard effect is a sample from the Vienna Boy’s Choir which haunts the song like a phantom as Bazan stirs over how much of his kids’ childhoods he’s missed. “Your kids are growing up/And you still don’t make enough.” The last time I saw him he went on a long tangent about how he was going to make more money on the next tour so he could take time off and build his daughter a treehouse.

96. “Scenery”- Ryo Fukui

The closer and title track to an overlooked gem of a jazz record, “Scenery,” ends things on a somber note. The drums and bass are just barely audible, occasionally lifting the wilting piano line when it seems like it just can’t go on. There’s a definite Charlie Brown Christmas vibe to the song and, just like the film, it’s as beautiful as it is devastating.

95. “Them Changes”- Thundercat

Funk played with a face full of tears. The entire Brainfeeder record label had a few years of recovery after label stand out Austin Peralta passed away at 22. Flying Lotus made “The Boys Who Died in Their Sleep,” and Thundercat created “Them Changes” with teardrop bass notes and his gorgeous falsetto claiming “I’m sitting here with a black hole in my chest/A heartless, broken mess.”

94. “Empty Chairs at Empty Tables”- Les Miserables

Obviously nothing matches the live power of “Empty Chairs” when you can see the tears actually streaming down and a stage devoid of life. But even in pure audio format, “Empty Chairs” is a brilliant meditation on grief. A dexterous, powerful singer is needed for a song like this but, the most powerful moment comes from its frailest stanza, when Marius’ voice breaks during “My friends, my friends forgive me.”

93. “Mother, I’m Here”- Bastion OST

Full disclosure, I’ve never played Bastion and I’m assuming somebody has died when this song plays. It’s funny, video game death is something we as players just gloss over or see as an annoyance. But “Mother, I’m Here” reminds me that for these pixilated people, death is so much more.

92. “Jaded”- Lone

U.K. producer Lone is usually a maximalist, all the colors, all the synths, all the time. But when he focused on his inner Miles Davis for “Jaded” he created one of the most beautiful electronic songs of the 21st century. It’s another late-night song, in the same mood as Davis’ “Blue in Green,” but textured with a heavenly chorus, rainy synths and the chiming melody line. Around the bridge, the synths change tone and, when listening through earphones, the textures feel like they’re massaging the ears. It’s a small song, nearly fragile in statute, but does it ever pack a punch.

91. “Gnossiennes 1”- Erik Satie

Hey here’s another minimalist instrumental piece! But unlike “Jaded,” “Gnossiennes” looks to the darker corners. The loping piano line seems perfect for a walk in a cemetery and asks uncomfortable questions about grief as it gracefully limps away.

90. “Singing and Singing”- Timbre

While most of Timbre’s ultra ambitious double album Sun and Moon was a deeply positive affair, “Singing and Singing” is utterly downcast and dower. Over snaking violin and harp lines, Timbre conjures up poisonous imagery and self-doubt. “Why must I become the rose that only shows its thorns?/Pruning back what I thought was growth?” It’s a sobering outpost in the middle of sun soaked melodies.

89. “Automatic Stop”- The Strokes

The Strokes always seemed like the coolest guys in the room. All leather jackets, jadedness and sharp guitar riffs. Turns out even the popular kids get rejected from time to time and when they have hooks like this, it creates something as catchy as it is crushing. Every time Julian Casablancas forces “why can’t you waaaaaaaaait” out of his throat and slides into “I’m not your friend/I never was” there’s no amount of aloofness that can stop the tears.

88. “Face to Face”- Daft Punk

Yes, Discovery was a non-stop dance party, but it was also the world’s most emotional dance party. “Digital Love,” “Something About You,” even “One More Time” held deeply romantic and emotional ideals, but nothing quite matched “Face to Face.” The chopped up samples hint at sadness at the club, but Todd Edwards’ soulful performance takes it over the top, landing it in the grand tradition of bawling and dancing at the same time.

87. “Daddy I Cut My Hair”- Daughn Gibson

The southern gothic world of Daughn Gibson is filled with prostitutes, con men and cowboys. Gibson’s deep baritone gives voice to the darker alleys of the globe so of course he’s going to touch on some somber material, but nothing was the same as “Daddy I Cut My Hair.” It follows the story of a young man freshly released from a mental institution, attempting to fit back into the outside world. All of it is boosted by oceanic synths and a caterwauling violin sample. “Daddy I cut my hair/I don’t look crazy now,” Gibson sings, terrified he hasn’t fooled anyone.

86. “Hope There’s Someone”- Antony and the Johnsons

Antony (now Anohni) has one of the world’s strangest voices, simultaneously powerful and brittle. No song quite fits her voice like “Hope There’s Someone.” A death-bed plea, Anohni harmonizes with herself, growing more otherworldly as the song speeds up and eventually forms a maelstrom created by hundreds of Anohni’s and a clattering piano, like we’re hearing her pass into the next world as the song closes.

85. “No Distance Left to Run”- Blur

Damon Albarn is really good a sounding tired. “Beetlebum” was sleepy sexiness, “Everyday Robots” was tranquil melancholy, but “No Distance Left to Run” is that left out to dry tired. The tired after a thousand fights, broken dishes, beds left cold. There’s none of the “WOO-HOO” energy from “Song 2.” It left a long, long time ago.

84. “Holocaust”- Big Star

Can’t really get worse than that title can you? And somehow, Big Star live up to it. The weeping guitars surrounding that downtrodden piano line are nearly out of ear’s reach. Alex Chilton sings a sort of anti-lullaby, for when the body has finally run out of tears. Picking a single moment of depression is impossible, between the death of a mother and not recognizing yourself in the mirror, but maybe the final stanza does it: “You’re a sad-eyed lie/You’re a holocaust.”

83. “Am I Born to Die?”- Tim Eriksen

There’s a grand tradition of death dirges from the American southeast. Appalachian music that stares the grim reaper dead in the eye and asks what the life thing is all about. Violinist Tim Eriksen adds to that long list of songs with just his violin and voice asking questions that won’t be answered until the curtain closes.

82. “Black”- Pearl Jam

Bitter doesn’t even cover it. Sang by every broken up boyfriend during the early 90s, “Black” is the furious response to the moments (or weeks, or months, or years) after “the one” leaves. “All I taught her was everything,” Eddie Vedder growls just before the chorus. It would be so easy for this song to just dissolve into meaningless nastiness, but the final plea of “I know you’ll be a star in somebody else’s sky/But why, why, why can’t it be, can’t it be mine?” shows that the raw anger is only hiding an ocean of sadness.

81. “$ Vic/FTL (Me and You)”- El-P

The death of New York artist Camu Tao will come up again on this list, but this is a hell of an introduction. Tao was a mainstay in the underground rap scene and his passing away from lung cancer in 2008 is still rippling through the music of his friends. El-P’s first album since Tao’s death was named Cancer 4 Cure and its final song was an eight-minute epic that floated through El-P’s own deep insecurities, anxieties about death and, above all, a mourning for his friend. “And I can no longer contain what’s under my disguise/I’ve always had the cancer for the cure/That’s what the fuck am I,” El raps, his voice almost breaking, admitting that his own self-destruction might be so out of control that it’s become the defining feature of his life.

80. “The Same Deep Water as You”- The Cure

So I had to pick one song from The Cure. There’ll be plenty of other bands where picking a single track was a nightmare, but The Cure has so many different facets to their sadness. I had to go with the most abyssal of all their tracks, the nearly 10-minute-long “The Same Deep Water as You,” which is, yup, a meditation on drowning both figuratively and literally. And it’s all as oceanic and suicidal as you would expect. “Kiss me goodbye,” Robert Smith moans before he’s gone into the black water.

79. “It’s Cool We Can Still Be Friends”- Bright Eyes

I had a Facebook poll asking for sad songs and this was, by a large margin, the most suggested. It’s easy to see why. All lo-fi sadness, Conor Oberst hangs out with his ex and regrets it the whole time, remembering the times without awkward silence and unspoken aggressions. By the end of it he’s stupefied by whisky and facedown on the floor, just to forget her face.

78. “Parasite”- Nick Drake

We’re in for a surreal bit of sadness here. Nick Drake’s obscure tale about hanging out with a crying clown and “traveling far in sin” doesn’t seem to have a direct plot, but there’s enough self-loathing contained with in to propel the song. “I am the parasite who hangs from your skirt” Drake sings as his haunting guitar refrain slowly disappears.

77. “The Thrill is Gone”- Chet Baker

It’s that voice. It’s not powerful. It’s not bombastic. It’s not technically perfect. It’s just a wisp of smoke floating through the door. Chet Baker’s thin, impossibly pretty voice only helps this standard wade into darker and darker waters.

76. “Hurt”- Nine Inch Nails/Johnny Cash

Though Trent Reznor eventually said that “Hurt” had become an entity beyond him when the Man in Black covered it, both versions cut to the bone, just in different ways. Original is more eerie, laced with dread alongside depression. Cash’s version just sinks like a stone into the depths of sadness. There are no other emotions seen or felt. I my mind, both are flawless reflections on self-destruction and regrets.

75. “Lonely”- Tom Waits

Closing Time isn’t the original sad barfly at a piano album, but it might be the best. Each song staggers along with a jar of whisky, broken chords and Tom Waits’ unforgettably grizzled voice. Waits has seemed like the elder statesman of American music for decades now but, somehow, he made this perfect slice of isolation at the young age of 24.


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