Let's hear your nominees. I'll put a few out there:
Hurt (any version is equally affecting; here's a duet with Bowie, here's Kermit)
Why it's the saddest song: "What have I become, my sweetest friend? Everyone I know goes away in the end ..."
Strike against it: Reznor got rich, famous and happy with music like this. Kinda undercuts the whole premise of Emo misery.
The Only Answer (ignore the video, just listen to the music)
Why it's the saddest song: "Five years in the wrong I am assured, my name to you is just another word." Great zinger for a lost love, you gotta admit. We've all been there.
Strike against it: Maybe a little too up-tempo to be the bummer music of all time.
The Ballad of Hollis Brown
Why it's the saddest song: Well, it does describe a seven-person murder/suicide from the most sympathetic possible perspective. Points for weirdness at least.
Strike against it: Maybe too horrifying to be strictly sad.
Rollin' By
Why it's the saddest song: The death of an entire town: "Me I stand here at the last filling station, while the wind moans a dirge to a coyote's cry."
Strike against it: How sad are we supposed to get about the passing of a community?
I could go on, but I'll stop there for now. So far I think I'd have to give the title to Hollis Brown, even if it is a little bit grotesque.
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