Photo: Courtesy of Anti- Records

The 15 Best Tom Waits Songs

From apocalyptic blues boasts to backwoods chant-alongs, here are 15 of the best songs encapsulating 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 7 December 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.”

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.

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 Weill 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.