(13) Depeche Mode, "Blasphemous Rumours"
So here’s another obvious band inclusion but a surprisingly difficult song choice. Darkness is everywhere in their discography, but it's maybe darkest here. “Blasphemous Rumours” begins with a 16-year old attempting suicide, and only gets blacker from there, as the song suspects that “God’s got a sick sense of humor / that when I die I expect to find him laughing.” Most of DM’s songs (“Black Celebration,” for instance) revel in the darkness they find themselves in, but not this one. Later they’ll find religion, of a sort, but not here: this song makes its case for the unfairness of the godless world: “girl of 18 / fell in love with everything / found new life / in Jesus Christ / Hit by a car / Ended up / on a life support machine.” There is no condolence or joy in this song—nor, perhaps, in the world, for those of us who pay attention. Matching up with Jules below (a song written in 1982, two years before this song, though Jules recorded much later) is a song with a weirdly similar message. One difference, perhaps, is that Depeche Mode's angle of attack feels a lot less passive, so we have Jules on upset alert.
(4) Gary Jules, "Mad World"
If you’re looking for reasons to pick against Jules, here are two: first, it’s a cover (as at least two other songs in the bracket are), and second, it was evidently released in 2001, recorded for the movie Donnie Darko, so it’s the latest song in the bracket, and the reason the ending date is 2001. But listening to it, perhaps because the Tears For Fears version is from 1982, so the song almost bookends the entire era, it feels like it’s been with us forever. I guess I was aware of the original, though it was never a favorite or a big single in America, but, man, it was brilliant in Donnie Darko, wasn't it? Your memories of that film may affect your fondness for this song. But it really struck a cultural chord: check the Wikipedia page for the Jules version to see how many times it’s been used in television shows since it came out (lotsssss). From that it seems clear that it’s indispensable for describing a particular kind of emptiness. It’s unadorned, unshowy. This isn’t a song that’s going to overwhelm you with sadness, but the dark heart's there if you’re ready for it. The Michel Gondry-directed video may offer it a bit of an unfair advantage in this matchup versus the videoless "Blasphemous Rumours," but that and the use of it in the film is why it's the 4 seed.