The 15 Best Tom Waits Songs

5. “Temptation” (Franks Wild Years, 1987)

Waits grew up in California, taking frequent trips to Mexico, so the Latin tinges in his music are deeply ingrained. That falsetto, though (which he refers to as his “Prince voice”) comes from somewhere else — it’s like a tailored shirt that got dragged through a briar patch on its way to your back. “Temptation”‘s slowly percolating rhythms and broken-jukebox horns all add to one of the best vocal performances Waits has ever turned in: play this to your friends who think he’s just a bellower.

4. “Hang on St. Christopher” (Franks Wild Years, 1987)

Demented horns, tribal percussion, needlepoint guitar, and Waits’ voice through a police bullhorn: this is about as close to an archetypal Tom Waits song as you can get. Fortunately, it’s just fucking awesome. St. Christopher ain’t the only one who should hold on when you put this one on.

3. “Gun Street Girl” (Rain Dogs, 1985)

There aren’t many Tom Waits songs like “Gun Street Girl”. Built on minimalist bass, percussion, and banjo, the tune’s singsongy, half-chanted vocal line is a winding narrative of fugitives, murder, and the woman at the center of it all. It’s strange, catchy, and like all the best of Waits’ songs, it creates a world of its own that draws you in and keeps you there, whispering secrets about day-old bread soaked in kerosene and the gun street girl who was the cause of it all.

2. “(Looking For) The Heart of Saturday Night” (The Heart of Saturday Night, 1974)

No bellowing. No brake drums. No turn-of-the-century railroad slang. Just acoustic guitar, upright bass, and one of Waits’ most unaffected vocal performances. The song’s sense of youthful yearning is only slightly offset by melancholy — even the best Saturday night turns into Sunday morning at some point. Even at 25, Waits could pack a couple of extra decades worth of sadness into hard truths like that.

1. “Christmas Card From a Hooker in Minneapolis” (Blue Valentine, 1978)

There are more creative Tom Waits songs and ones that he actually, well, wrote (“Christmas Card” is adapted from a Charles Bukowski poem called “Charlie I’m Pregnant”), but there aren’t quite as many that can utterly devastate a room full of people with quite the same slurred, finely-detailed aplomb. For maximum tears in your bourbon, watch this live version, which features a bedraggled interpolation of “Silent Night” and Waits’ rendition of that Little Anthony and the Imperials record. The audience laughs a bit at some of the lyrical gems, but after that final verse, you can hear a pin drop.

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This article originally published on 9 January 2013.