My friend Kyle and I used to make up these games, in which we would try to list the top ten songs/artists in an invented category, mostly to keep us occupied in the culturally-vacant wasteland that was State College, PA. Often, determining the category was as fun as filling it out, and Kyle was particularly brilliant at category constructions. Some examples: "Top Ten Artists that You Know You SHOULD Love But You Secretly Hate" (Both Kyle and I listed Jim Morrison/The Doors as #1); "Top Ten Great Singers Without 'Great' Voices" (I think Kyle said Nina Simone... mine was Leonard Cohen); "Top Ten Rock Anthems" (me: Styx's "Come Sail Away", Kyle: The Rolling Stones' "Paint It Black"). Et cetera, et cetera, et cetera...
Once, Kyle presented the following category: "Top Ten Saddest Songs EVER." Now, I'm sure you're thinking that you could easily rattle off ten sad songs without much effort. And, of course, so could Kyle and I. But that wasn't the point of the game, as we saw it. We took great effort to make sure that our top ten lists only came at the end of much thought and deliberation (and beer). We also were careful that our selections were non-obvious ones. We must have debated dozens of potentially list-worthy songs that night before settling on our ten. I wish I could remember all of the finalists, but I don't. (I do recall that I cheated just a bit in this category and included one of my own songs, "Heart of Stone.") However, I have never forgotten Kyle's choice for #1 Saddest Song Ever... Bob Dylan's "Don't Think Twice, It's All Right." (That's a link to Dylan performing the song on YouTube. You should watch it.)
It's such an obvious selection in some way... and, yet, I doubt anyone with insight, sensitivity and erudition only a hair shy of Kyle's (which is almost everyone) would have thought of it. The context of Dylan's story in "Don't Think Twice" is post-breakup, the perfect mise en scene for sad songs. But instead of a lot of wailing and moaning and gnashing of teeth, its voice is one of (to borrow a trope from Kierkegaard) infinite resignation. The coup de grace comes at the end, after Dylan's ambling but concise account of the love that was never meant to be. He sings:
I'm walking down that long lonesome road, girl
Where I'm bound, I can't tell.
Goodbye is too good a word, gal
So I'll just say fare thee well.
I ain't saying you treated me unkind.
You coulda done better, but I don't mind.
You just kinda wasted my precious time.
But don't think twice, it's all right.
Ouch, baby. That hurts. That really hurts. It's just this kind of resignation that captures what is so, so sad about lost loves. And it's just this kind of attempt at being okay, this shoulder-shrugging stoicism-- so earnest and so false at the same time-- that drives home the hurt that lies beneath. A masterful song, really.
On a related note, I've said for many years that the best songs are sad songs. (That's why I like country and blues so much.) I've never been able to write a "good" song that isn't generously seasoned with sadness. I just don't know how to do it. Anyway, I'm opening up the comments section of this post for your additions to the list of "Saddest Songs Ever." Which tunes tug at your hearts?