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The 15 Best Tom Waits Songs

Photo: Courtesy of Anti- Records

From apocalyptic blues boasts to backwoods chant-alongs, here are 15 songs that encapsulate Tom Waits' incredibly varied career.

It's difficult to write a proper introduction to any piece about Tom Waits. If you're a fan, you'll already know everything I could say about him. If you're not, here's what Wikipedia has to say: "Thomas Alan 'Tom' Waits (born December 7, 1949) is an American singer-songwriter, composer, multi-instrumentalist and actor. Waits has a distinctive voice, described by critic Daniel Durchholz as sounding 'like it was soaked in a vat of bourbon, left hanging in the smokehouse for a few months, and then taken outside and run over with a car.' With this trademark growl, his incorporation of pre-rock music styles such as blues, jazz, and vaudeville, and experimental tendencies verging on industrial music, Waits has built up a distinctive musical persona."

So, um, there.

Waits' music treads so many stylistic paths that the challenge I wanted to present myself with here was, "In just how few songs can you sum up the man's music?" Fifteen was about as close as I got. The goal here wasn't just to put the songs on here that I couldn't live without (because I left off, oh, say, 50 or so), but to find 15 songs that represent every facet of Waits' music: the backwoods, the cabaret halls, the grimy sidewalks. It was a challenge, to say the least.

Pink Fender by rahu (Pixabay License / Pixabay)

15. "Just the Right Bullets" (The Black Rider, 1993)

Tom Waits' music has always had an odd theatricality to it, borne of (I think) a fascination with Kurt Veill and Bertolt Brecht. Never has this been so apparent as in The Black Rider, a "musical fable" produced in collaboration with William S. Burroughs and Robert Wilson. "Just the Right Bullets" is a bizarre combination of lurching, music hall cabaret, and surging, double-time instrumental passages -- I think it's as appropriate as any cut to demonstrate Waits' theatrical leanings.

14. "Hell Broke Luce" (Bad As Me, 2011)

Taking its title from a piece of graffiti carved into the walls of Alcatraz during a prison break, "Hell Broke Luce" finds Waits agitating on behalf of one of his favorite causes: the beleaguered Army grunt. But this isn't a tender ode to homesickness like Real Gone's "Day After Tomorrow": this is an apocalyptic field chant that conjures visions of a dusty, demoralized desert before strafing it with Keith Richards' and Marc Ribot's guitars. Fittingly for someone who's spent a career chronicling the least among us, Waits hurls vitriol for those at the top: "How is the only ones responsible for making this mess / Got their sorry asses stapled to a goddamn desk?"

13. "Goin' Out West" (Bone Machine, 1992)

Stark, eerie, and hilarious, "Goin' Out West" is the highlight of Bone Machine. Its genius is the naked ambition and hilarious blues boasting in the lyrics ("I'm gonna change my name to Hannibal / Or maybe just Rex") that butt up against the end-of-the-world menace of the band's relentless swing.

12. "Anywhere I Lay My Head" (Rain Dogs, 1985)

At a New Orleans funeral, it's traditional to have a brass band play a song as a dirge on the way to the cemetery and then as a high-spirited march on the way back. "Anywhere I Lay My Head" has the same construction -- it's a mournful, nakedly emotional song of resignation that fades into a beautiful, uptempo march at its end, with Waits banging away at a huge bass drum as he and the band strut out of the cemetery.

11. "16 Shells From a Thirty-Ought Six" (Swordfishtrombones, 1983)

A shuffling, slouching tale of a long strange trip through some unnamed wilderness with a crow trapped in a guitar and a mule as traveling buddies, "16 Shells" was borne of Waits' obsession with old prison work-gang chants. If you aren't terrified by Waits howling "I'm gonna whittle you into kindlin'", then you're made of sterner stuff than I am.

10. "Step Right Up" (Small Change, 1976)

Much of Small Change finds Waits dipping dangerously into zeeba-baba-doo-ba "gee ain't I the hippest cat" territory. That said, you are a humorless prick if "Step Right Up" doesn't astound and delight you. A litany of huckster come-ons over a dangerously limber jazz trio, "Step Right Up" is positively one of Waits' most incredible vocal performances: it's hilarious, it's athletic, and it contains the indelible line, "The large print giveth, and the small print taketh away." This live version is slower than the record, as if Waits knew that was a feat he couldn't replicate nightly.

9. "Jockey Full of Bourbon" (Rain Dogs, 1985)

Another positively iconic Waits tune thanks to its use in Jim Jarmusch's Down by Law. "Jockey" cruises in second on hand drums, upright bass, and Ribot's guitar set to "stun". Waits' vocal proves he doesn't have to bellow to cast his spell -- his sandpapery whisper paints images both baffling ("And I've been stepping on the devil's tail / Across the stripes of a full moon's head") and terrifying ("Bloody fingers on a purple knife").

8. "Hoist That Rag" (Real Gone, 2004)

"Hoist That Rag" sounds like it was recorded in a raft that just left Cuba. And I mean that in a good way. Listening to Waits shift between his high, keening register on the verse and that rafter-shaking bellow on the chorus is an unmatched thrill, and Marc Ribot turns in a hypnotic, catchy gem of a solo midway through.

7. "Downtown Train" (Rain Dogs, 1985)

The irony in this song being covered by Rod Stewart is that Waits' original version comes closer to the brandy-soaked, rough-edged charm of Stewart's early records. That's Richard Hell and Lou Reed's old bunky Robert Quine playing guitar, and aside from Waits' husky, strained vocal, his guitar is the real soul of this song. "Downtown Train" is wounded, lonely, but still ultimately hopeful -- Waits in a nutshell.

6. "Warm Beer and Cold Women" (Nighthawks at the Diner, 1975)

Early Tom Waits was often in danger of be-boppin' and finger-snappin' his way into caricature, but "Warm Beer and Cold Women" walks the line between character and caricature beautifully. It helps that Waits assembled a top-notch band of L.A. jazz session vets to help his song softly strut through Nighthawks at the Diner -- Pete Christlieb's deftly supportive sax and Jim Hughart's supple bass work elevate this tune to the closest Waits ever got to pure jazz.

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.

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