Why is this song so sad? There are other sad Tom Waits songs–I’m thinking “Broken Bicycles,” “Hold On,” the magnificient “Kentucky Avenue.” There are even a few other songs on this album, “Heartattack and Vine,” that give it a run for its (sadness) money, like “Saving All My Love For You” and “On the Nickel.”

But this one…it’s a moment that should be from a Jack Kerouac novel, a man leaving a woman in the early morning before she wakes up:

    I will leave behind all of my clothes I wore when I was with you
    all I needs my railroad boots and my leather jacket
    as I say goodbye to Ruby’s arms although my heart is breaking

Why is he leaving? We don’t know. An intractable sitution, the call of the road, he has another woman, she has another man: it could be any of these. There’s an inevitability to it, a resignation in the vocal, that makes you not worry so much about reasons. This is happening, this has to happen. There’s no other choice but to leave.

Perhaps for a moment your intellectual mind kicks in: okay, he’s leaving this woman he clearly still loves, that’s definitely sad, but it’s not like she’s dead. It’s not like he won’t be able to see her again if he really wants, give her a call some night, stalk her on Facebook. Why the ultimacy?

But maybe that’s part of what’s so sad about it. The song won’t admit any of those real-life possibilities. It lives in the ultimacy, puts forth this parting the way such partings feel in the moment, as if they are forever. I’m an older guy now, and don’t really believe in clean breaks anymore, but I did when I was 20, and this song reminds me of that.

What else makes this one destroy me every time I hear it? The Salvation Army Band horns that begin and punctuate the song; the touch-too-slow melody; the strings that swell up at the most emotional moments; the way the vocal, so understated all the way through, itself swells with emotion on the line, “So Jesus Christ, this goddamn rain.” That line itself, one of my favorites in the whole Tom Waits canon, so full of longing and powerlessness.

The intellectual mind again: it’s just rain, it’s going to stop eventually, and it’s not like it’s just raining on him, right? All true. But that’s sure not how it felt at the time.