#127, "If I Have to Go," Tom Waits (1986)

150 Favorite Songs: #127, "If I Have To Go," Tom Waits (1986)

Tom Waits has written more famous songs, but I don't think he ever wrote a sadder one. And for all I gush about loving poppy songs, or aggressive ones, or energetic statements of rock and roll fury, or whatever, I love my sad songs best. The saddest song that Tom Waits ever wrote is a good candidate for the saddest song ever written, and "If I Have To Go" is certainly on that shortlist.

"If I Have To Go" was written for and performed during the Frank's Wild Years stage show, which ran in Chicago in 1986, but the recording didn't get released until a couple of decades later. It's incredibly vivid as a part of a narrative, though. The singer explains his plans clearly, says goodbye in a way that hurts, expresses some bullshit notions that Waits doesn't try to pretend are fair, and generally just aches on your stereo.

Because those words. Until I send for you, don't wear your hair that way / if you can not be true, I'll understand. Yeah, he's leaving her and leaving her instructions, insisting that she keep waiting—but over the course of the next verse, it becomes clear that he knows that it's over. Tell all the others you hold in your arms / I said I'd come back for you, he sings, but if he meant it, he'd tell them himself. And I think that's why this song gets to me so much. Because it's not just about leaving, it's about the lies that people tell themselves to make leaving feel okay somehow. There are so many great songs about leaving, but very few that capture that side of it.

And of course he says it with one of the prettier piano melodies he ever came up with, because why wouldn't he?

There aren't a ton of sad songs that I first heard after Kat and I got together that really speak to me. That's just part of growing up. If I'd heard "If I Have To Go" when I was twenty and breaking up with my first serious girlfriend, it would mean something completely different. That would mostly be bullshit—ours was not a great love—but music like this makes you want to feel the things it reaches for, and so I might have played it for days on repeat. But that almost makes it even more significant. I feel "If I Have To Go" in a deep part of me even though I've never been able to relate to it. That means something special to me, these days.