10. Modest Mouse – “Little Motel”
Whether you interpret “Little Motel” as referring to a divorce, a disintegrating relationship, or even the loss of a loved one, there is nothing happy about this track. Isaac Brock’s subtle vocals over a minimalistic guitar set the tone, before the song explodes into a crescendo of guitar feedback and, well, sadness.
Saddest Lyric: We trade tit for tat, like that for this/And I don’t think that there was an insult that was missed/I can see it in your eyes, like I taste your lips/and I’m very sorry
9. Margot and the Nuclear So & Sos – “Jen is Bringing the Drugs”
Superficially, this is a song about a girl who started out young and innocent, but has become all sorts of depressed and fucked up. But in these three minutes of melancholia, you could also see the song being about just not giving a fuck about anything and doing drugs cause life sucks so much. Sad. Ness.
Saddest Lyric: ‘Cause love is an inkless pen/it’s a tavern, it’s sin/ it’s a horrible way to begin.
8. Elliott Smith – “The Biggest Lie”
Elliott Smith was not a very happy dude. He was a hardcore heroin addict, a debilitating alcoholic, and oh yeah – he killed himself. Elliott was one of the most talented songwriters of the nineties, but he never achieved huge mainstream popularity – probably because all of his songs were so damn depressing. The saddest of his sad songs, “The Biggest Lie,” ain’t exactly partying music.
Saddest Lyric: Oh we’re so very precious/you and I/And everything that you do/makes me want to die.
7. Mineral – “Slower”
Mineral was a little-known rock band of the mid-nineties who only released two full albums. However, that first album, The Power of Failing, spawned one of the saddest songs ever, which doubles as one of the best “Fuck the world” songs ever. “Slower” is the only entry on this list that might prompt you to blow up a building instead of slitting your wrists.
Saddest Lyric: It’s just not the same when you’re staring into a perfect golden sunset/when you’re thinking about how you sold your soul to send the rain away.
6. Radiohead – “No Surprises”
When asking others for thoughts on the saddest songs ever, a number of songs off Radiohead’s OKComputer were mentioned, in an unsurprising development. That entire album is fucking crushingly depressing. But the saddest song on the album might just be the deceptively tragic “No Surprises.” The sad lyrics are propped up by a facade of strings and bells and keys, but when you look a little deeper, “No Surprises” makes you wish you hadn’t, cause, like, now you’re really sad.
Saddest Lyric: I’ll take a quiet life/A handshake of carbon monoxide.
5. Warren Zevon – “Keep Me in Your Heart”
Ah, Warren Zevon. The man behind 70s and 80s mega-hits “Werewolves of London,” “Carmelita,” and “Lawyers, Guns, and Money,” to name a few. The man partied hard and rocked hard. So why is this song on this list?
Well, on the surface, “Keep Me in Your Heart” sounds like an uplifting-enough little number, maybe about a breakup or something. But when you realize that Mr. Zevon was quite literally dying of cancer while he recorded the song, it takes on a whole new level of sadness and sentimentality; “Keep Me in Your Heart” is Warren Zevon’s final wish – that his loved ones remember him when he’s gone. The feels, man.
Saddest Lyric: If I leave you it doesn’t mean I love you any less/Keep me in your heart for awhile.
4. Death Cab for Cutie – “What Sarah Said”
Brooding piano, the intrinsically sad vocals of Ben Gibbard, and, well, a chorus of “Who’s gonna watch you die?” makes for one of the most depressingly beautiful songs ever written. Death Cab paints a perfect picture of sadness by setting the atmosphere of a man in a hospital, waiting for news about his gravely ill loved one. If you’re already feeling shitty, this song might just ruin your entire month…proceed with caution.
Saddest Lyric: I rationed my breaths as I said to myself that I’d already taken too much today/As each descending peak on the LCD took you a little farther away from me.
3. Manchester Orchestra – “Sleeper 1972″
I’m a big fan of Manchester Orchestra, and mostly, they write some uplifting, kickass rock n’ roll. But on their debut album, I’m Like a Virgin Losing a Child, Andy Hull and Co. dabbled in just some run-of-the-mill, totally fucking soul crushing music. The best example? “Sleeper 1972.” You don’t need to even make this song relate personally to understand how depressing it is. When a track opens up with the lyrics “When my dad died, worms ate out both his eyes,” you pretty much understand that good times are not in store. But it only gets worse. Oh, it only gets worse.
Saddest Lyric: You told me this has always been worth living/What’s really worth living anymore?
2. Red House Painters – “Katy Song”
Ugh, this one is brutal. “Katy Song” isn’t about death, but it’s about the worst kind of love – the unrequited kind. Through eight minutes of haunting, half-spoken vocals, and guitar and drums ambling about in melancholy, the Red House Painters evoke every bit of sadness you’ve ever felt about a girl or boy who didn’t love you back and multiply it times one thousand. Seriously, if you just got out of a bad breakup, or if the person you love loves someone else, DO NOT listen to this song. I warned you.
Saddest Lyric: By the forest of our spring sta /Where you walked away/And left a bleeding part of me/Empty and bothered/Watching the water/Quiet in the corner/Numb and falling through/Without you what does my life amount to?
1. Johnny Cash – “Hurt”
Yep, the 1 saddest song of all time is a cover song. The original version, by Nine Inch Nails, is probably more aesthetically depressing, but when you take this song and all of its depressing lyrics and combine it with a 71-year-old man, only a few months away from dying, it makes for a veritable truckload of the FEELS.
The last single Johnny Cash ever released before his death, “Hurt” was accompanied by a downright depressing music video, in which the old man reflects on his life and his impending demise. When Cash sings “You could have it all, my empire of dirt,” it really hits a nerve; the old man knows he’s in the twilight of his life and his career, and that all the goals he’s ever attained will soon be lost to the ages. It’s all sorts of crushing.
Saddest Lyric: You could have it all/my empire of dirt/I will let you down/I will make you hurt.