(6) Kate Bush, "This Woman's Work"
Uh, wait, what? You say Kate Bush wrote the song specifically for a scene in a John Hughes movie? Well, that doesn’t add to the sadness quotient of this song exactly, but it does up its awesome quotient. For instance, navigate to around the halfway point of this helpful cut of the scene for the montage set to song (she apparently wrote the lyrics to the content of the montage: is that horrible or is it great?). More videos should have montages, really, and the official video version kind of does, as it turns out, though in a super Kate Bushy way. Or really, just watch the first simply awesome minutes of the 1979 Kate Bush Christmas Special. Just two minutes, and either you're going to vote for Kate Bush or vote against Kate Bush based on that. Either choice is fine. Honestly, if you added the weird diaphanous bat cape from the first scene of the Christmas special to this song or video you'd have a winner and I'd vote it all the way to the finals based on that. But the more I watch these clips the more I end up talking myself either out of or into this song. I really can't be sure which. But I'm feeling a lot more of something for this song and for Bush. As you know Maxwell does a pretty great cover of this song, which you can look up for yourself, though we have a hard time imagining it'll affect what you think of it in the way that the Johnny Cash version did of "Hurt." I don't know what else to tell you about the song.
(11) Sisters of Mercy, "Some Kind of Stranger"
Goth is a tricky thing to navigate vis-à-vis sadness: the whole genre is a downer, though it rarely seems particularly sad. I would have guessed in the early stages of selecting songs that the tournament would be seeded with goth, but it hasn’t worked out that way. That’s because, while punk essentially says (I’m paraphrasing the introductions to the Joy Division box set, I think, and not super well, like I'm trying to Brian Blanchfield this up and not resort to actually looking up sources) “fuck you,” goth says “I’m fucked,” or in some cases “we’re fucked: we might as well take amphetamines and try to find someone or something beautiful.” Well, the Sisters of Mercy tend toward the political (not always to their credit) they're best when they're a little more danceable (not to say dancy), but this track, a selection from First and Last and Always, arguably their best album (personally this committee member will always take Floodland, but he understands what was lost when Andrew Eldritch fired the rest of the band and took things in a new direction, and it’s increasingly obvious that First is a peerless album), is sheer desperation, total sadness. It should also be pointed out that this particular member of the committee finds it impossible to separate himself from his longtime love of this band to be in any way objective about this choice. As far as he's concerned, you should be picking Sisters of Mercy here for the upset. Really, if it's Sisters of Mercy or John Hughes movie song, what choice do you have? Sisters of Mercy would definitely bring the bat cape to the video if they had one.