This list was inspired by one posted on a Village Voice blog last year. While perusing that list, I was struck by how tired all the choices seemed. Sure, a lot of their picks are really pretty sad (Joy Division, Elliott Smith, Billie Holiday), but there’s just so much more music out there than the fucking Counting Crows and Bon Iver. To me, it was a bit of a disservice to both sadness and music, so I present you with my version instead. I did my best to stay away from more well-known music (except for a handful of well-deserved but recognizable choices), but everything is subjective, so, you know, whatever. Here goes nothing.
1. Michael Gira - Drainland
Everyone knows that couple that seems to belong together yet can’t quite make it work because one of them is an alcoholic or drug addict or something else that gets in the way of a healthy relationship. “You See Through Me” is an audio version of that couple’s agony. Even if you don’t love Swans, Michael Gira, and Jarboe (which I do, all three), this song will break your heart into a million pieces and, if you do love all three, it will make you question your love of at least one of them. The rest of the album (see “Why I Ate My Wife” and “Blind”) is also pretty sad, but I dare you to make it to the end of “You See Through Me” without bursting into tears. I sure as shit can't.
2. Townes Van Zandt - For the Sake of the Song
Country’s saddest troubadour. Is there anyone who can make a syllable, any syllable, sound more pain-filled than Townes? It was difficult to choose just one of his albums (Our Mother the Mountain was a strong contender, and “Lungs” is quite the gut-puncher) but I ended up picking this one because I know it the best, and because “Sixteen Summers, Fifteen Falls” reduces me to a puddle of shuddering sorrow (the title says it all) and I’ve always preferred this earlier version of “Waitin’ ‘Round to Die” since that whole ‘miserable lyrics paired with mismatched catchiness’ thing always does me in.
3. Gil Scott-Heron - I’m New Here
Right from the opening track, which features Gil Scott-Heron talk-rapping about his experience being raised by his grandmother, this album just fucking beats you down. A soul poet with political leanings that easily made his mark in the ‘70s (he was the original Saul Williams), Gil Scott-Heron hadn’t released a new album for 16 years before this one came out, with 12 years stretching between even that release and the next, largely due to his battles with various drug addictions and related charges. The style here is unapologetically confessional, diving deep within himself rather than reflecting the outer tensions of the world like much of his earlier work. He died just over a year after I’m New Here came out, crushing any possibility of a further comeback and devastating the hip-hop/soul community he had influenced so well. This album is post-modern blues poetry of the truest, saddest order, and if that doesn’t make your whole body quake with anguish, you simply do not have a heart.
4. Shataan - War Cry Lament
While not technically a proper album, this demo more than earns its place on a list of music about terrible sadness. Raw, psychedelic blackened folk from the Black Twilight Circle out of Southern California, Shataan is the music of the Trail of Tears and injustice against native peoples. I challenge you to find sadness that’s less bullshit than that.
5. Blood & Time - At the Foot of the Garden
Listening to this album is like holding someone’s beating heart in your own hands and feeling the encasing blood drip down around you. Scott Kelly, one of the fine men behind the progressive metal powerhouse that is Neurosis, is the brilliant mind behind these hauntingly beautiful, deeply personal songs. I just don’t think I have the words to truly articulate how much this album means to me, but I’m sure it meant far more to him.
6. Father Murphy - Pain Is On Our Side Now
This recording (an EP, not an album, but whatever) is self-professedly about failure, and what’s more sad than the painful realization of not only your own failure, but also that of others? I suppose sadness isn’t necessarily always equated with pain, but it pretty much is in my world, and for that, you can’t get more painful than Father Murphy. Their music is magical and heartbreaking and thunderous in a rather quiet way, which, for me, is an awfully accurate rendering of most of the sadness I’ve ever known.
7. Hell - III
I had the distinct pleasure of witnessing a Hell live performance last year, and it was easily one of the most devastating, gratifying shows I’ve ever attended. “Mourn” is, hands down, the saddest sludge song I’ve ever heard - listen to that intro and remember every tear you’ve ever cried, and then maybe cut yourself. Or not, if you’re not into that sort of thing. But I bet you might want to.
8. Neil Young - Tonight’s the Night
If you’re a Neil Young fan, you are undoubtedly aware of the catalyst behind these songs. If you aren’t a Neil Young fan, you should be, but I’ll tell you anyway that the songs on Tonight’s the Night were written only a few months after the drug overdose deaths of not only Crazy Horse guitarist Danny Whitten, but also Neil’s friend and roadie Bruce Berry. All I can say is that death is forever, and even though it’s inevitable, when it’s drug-related, it just tends to cut to our very cores, because we know it could have been prevented, but we are forced to accept that there’s nothing we could have done anyway, since we just won’t be able to live with ourselves otherwise. This album doesn’t quite make me weep like some of my other choices do, but I suspect that has more to do with Neil Young’s idiosyncratic voice than anything else. It is undeniably a terribly sad album, and absolutely belongs on this list, and any list of sad music, really.
9. Abner Jay - True Story of Abner Jay
In my view, there’s a kind of inherent sadness to outsider music; couple that with blues, the most naturally sad music of all time, and you get Abner Jay. Thanks to Mississippi Records, there’s this nice compilation of some of his best miseries. “St. James Infirmary Blues” is a classic sad song, but how much sadder can you get than “I’m So Depressed”? Oh yeah, I think it might be “The Reason Young People Use Drugs”. Also, “Cocaine”. Fuck.
10. Slint - Spiderland
I fought with myself over whether I should include this album or not, but goddamn, it’s fucking sad, and it’s fucking great, and it definitely deserves to be listened to before you die, especially if you’ve never heard it before. “Don, Aman” is particularly visceral for me. When he sings or says or whispers, “It felt good to be alone,” I just want to rip my heart out. And then, of course, there’s “Good Morning, Captain,” which, damn. “I’m sorry…. AND I MISS YOU.”