(16) Violent Femmes, "Add It Up"
How does desperation and pissed-off-ness intersect with sadness? This song’s not an obvious mope on account of the relentless and let’s face it a little crazy anger, but that doesn’t mean it’s not sad. In a pissed-off and kind of unhinged weirdo bracket, Violent Femmes would come in with a top seed. But “Add It Up”’s sadness comes at a slant, and that’s why it’s only a 16 seed in this tournament. So expectations here aren’t high for Violent Femmes, and if this was a home game for them they might have a chance, but Neutral Milk Hotel also knows how to play an uptempo and unhinged genius weirdo style of game. This would be an upset for the ages, but that’s always been how Violent Femmes rolls. As always, they'll play as if they have nothing to lose.
(1) Neutral Milk Hotel, "Two-Headed Boy"
Almost any song from NMH’s 1998 album In the Aeroplane Over the Sea would have garnered a high seed; this is one of the dubious benefits of being pretty much the only piece of popular music about the life and death of Anne Frank. “Two Headed Boy” is a slightly lesser-known song from this much-praised desolate masterpiece. The lyrics about the “Two headed boy / All floating in glass” are both beautiful and disturbing, and the song as a whole lends itself to many interpretations (I like this one). Jeff Mangum’s vocals, which manage to sound both delicate and unhinged, make the song’s imagery devastating. Like all of the best sad songs, “Two Headed Boy” ends without consolation or pity: “The world that you need is wrapped in gold silver sleeves / Left beneath Christmas trees in the snow / And I will take you and leave you alone.”