Tom Waits’ Top 5 Sad Bastard Songs

You’re innocent when you dream, Dude.

Gary Chapin
The Riff
Published in
3 min readApr 4, 2021

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Detail from Bone Machine album cover

Keith R. Higgons posted a great piece yesterday about Sad Bastard Music.

Tom Waits writes songs that leave scars on you if you’re open to that sort of thing. People get the wrong idea — like wondering why he only writes about hobos, which isn’t true … read my satiric rebuttal of that canard — but one of the ideas they get right is that his songs are filled with, to use Keith’s phrase, sad bastards. Here are the top five sad bastard songs in Waits’ catalogue.

5. “Train Song” (Franks Wild Years)

It’s probably just a story about a wanderer who can’t get home, but it also might be an artful way to talk about suicide (“It was a train that took me away from here, but a train can’t bring me home.”) Either way, evokes that feeling of irrevocable decisions we make that separate us from those we love. The character of Frank is one of the great sad bastards in music.

4. “Cold Water” (Mule Variations)

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Gary Chapin
The Riff

Poet. Humorist. Storyteller. MuddyUm editor. I write. I have always written. I play accordion. I have an extraordinary ability to be fascinated by things.