Maybe it’s the weather, maybe it’s the dark, but I’m in a little bit of a wallow-y funk these days, where the only thing I truly want to do is to curl up, and catch up on some reading.  And by catching up on reading, I mean watch old episodes of Felicity and drink scotch. As any good wallower would know, setting the mood is critical.  In this vein, I give you my top three contenders for most depressing songs ever.  Let me know if I’m missing any good ones, will you?

Tom Waits, ‘I Hope That I Don’t Fall In Love With You’

I realize that Tom Waits’ body of work has many contenders for most depressing song, but I think what really sends this particular song to the top is that it’s preemptively melancholy about the possibility of being melancholy.  Like, hey if you’re going to be in the pits anyway, why not just start out there.  Oh, Tom.  Also, this gets my vote for most scotch-friendly song.

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Leonard Cohen, ‘Hallelujah’

For a long while, I liked the Rufus Wainwright cover of this song as well, but I’ve come around.  The original is the best.  Classy, operatic, and so f-ing sad.

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Radiohead, ‘Fake Plastic Trees’

A reminder that things don’t have to be tragic to be sad, they can be just so quietly, deadeningly boring.

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I guess what you can take away from all this is that if you want to send me into a sad downward spiral, just send over an older male with a raspy voice to serenade me.  Easy peasy.

A jaunty post is in the works, I swear.