Obviously, this is by no means comprehensive. In fact, I have only just begun. Turns out it is hard to come up with a list like this without needing to maybe go and lie down for a while. So I’ll start with these and then maybe revisit the topic at a later point after I have, you know, recovered. There are certainly obvious omissions (Johnny Cash’s cover of “Hurt” immediately comes to mind), but I’ll just leave it at these for now.
“Did I Tell You” by Yo La Tengo. Some people might find this song romantic and lovely, which it is, but it kind of kills me at the same time. Which certainly has never kept me from listening to it. Over and over.
“Cracking” by Suzanne Vega. “It’s a one time thing. It just happens a lot.” Oh man, that first album. Everything about it is so sad and lovely. And for me this song perfectly captures that feeling of aimlessly wondering through New York, which I have done over and over at various points of my life: “Through the park in the afternoon, wondering where the hell I have been.”
“To Live is to Fly” by Townes Van Zandt. Now if you know Townes, you know that it is nearly impossible to choose simply one sad song of his. I don’t think anyone knew heartache better than this man. “We got the sky to talk about and the world to lie upon.”
“Waltz #2 (XO)” by Elliott Smith. “I’m never gonna know you now, but I’m gonna love you anyhow.” Okay, I seriously need to lie down for a minute. Man.
“Save Me” by Aimee Mann. Oh, Aimee. That line about the freaks who could never love anyone.
“She’s a Jar” by Wilco. “We could use a hand full of wheel/And a day off/And a bruised road.”
“The Weight” by The Band. This version, the one from the album, is the one that does it for me every time. In high school I used to lie in the dark on my living room floor and listen to this song over and over. For me it is simply one of the best saddest songs ever. It’s pretty much where I started and where, at this point, I’m going to end.