(9) The Pretenders, "Back on the Chain Gang"
For better or worse, I am old enough to recall “Back on the Chain Gang”’s original release in 1982, and, even though I was only 8, I remember being arrested by the bleak drama of the bridge: “The powers that be / That force us to live like we do / Bring me to my knees / When I see what they’ve done to you” (aside: The Pretenders do really great bridges; the bridge for “Don’t Get Me Wrong” is my favorite bridge ever). I also remember taking the chain gang stuff really literally, and thinking that the song was about two lovers separated in some sort of Communist work camp scenario, which is extra funny to me after watching the anti-capitalist video. Political overtones aside, “Back on the Chain Gang” is about a lost love, a love that provided the singer with her only happy moments, “Like a break in the battle was your part, oh oh oh oh / In the wretched life of a lonely heart.” It’s also one of the more cynical songs in the bracket, not only because it equates life with being on a chain gang, but also because of the “circumstance beyond our control” that “Got in the house like a pigeon from hell oh oh oh oh / Threw sand in our eyes and descended like flies.” So, we’re all on a chain gang PLUS the world is a heartless place that will destroy all of our attempts to love. Thanks, Pretenders. You really showed up for March Sadness.
(8) Tom Waits, "Downtown Train"
The committee would like to state up front that there are other, probably sadder Tom Waits songs (“Time,” for instance, or “Georgia Lee,” or the almost-too-obviously-titled to be chosen “Christmas Card from a Hooker in Minneapolis,” or the serious fan could probably suggest another dozen, as we suggest you do in the comments), but this song's perfectly positioned on the edge between the pop hit and the strange lament. You might know it from its more famous Rod Stewart cover, or perhaps the kind of insane Patty Smyth (“The Warrior”) cover that you really must watch. It’s easy enough to go down the youtube hole on cover versions and wonder how these radically different artists found their way to the song, but the answer is largely that the original’s a brilliant—and brilliantly sad—song. Waits' is the original, if that matters, and I suppose it does enough to mention it here. His version retains a bit of the romance angle, but offsets it with the more obvious spastic drunken watcher angle. The thing that’s great about it, though, is that helmed by the inimitable Waits it’s still not creepy, or not totally creepy. The Rod Stewart version is creepier, frankly. This one's still sad, devastating really, still as forlorn as anything, still watching something it will never have, wanting, and knowing it’s just wanting that you’re feeling: “Will I see you tonight / On a downtown train / Where Every night its just the same / You leave me lonely.”