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The 30 Best Tom Waits Songs

Few musicians have captured the emotional complexity of being an American in the 20th and 21st centuries with as much elegance and nuance as Tom Waits. Blending blues, jazz, rock, and experimental music (among other genres), his tableaus of modern life find spiritual common ground everywhere—from Tin Pan Alley, Harry Partch, and Bob Dylan to Raymond Carver, Jack Kerouac, and Charles Bukowski.

Waits’ sound is all over the map—he likes tight jazz instrumentation, but orchestrates it to sound more like Captain Beefheart than Thelonious Monk. He loves percussion, but many of his greatest songs feature only light tapping, misty snare shuffles, or, often, no drums at all. His music sounds like it’s always on the verge of coming together, yet it has a cohesion and consistency that makes it immediately recognizable. Then there’s his voice, about which there’s half a century of vibrant metaphors and descriptions.

What really binds together Waits’ weird recipe of American music, though, is a deep-seated holding of the antinomies of the contemporary experience: love and despair, reverie and presence, anxiety and solace. His music is often strange, but its essence never is—throughout it is a wholly relatable palette of feelings and emotions. From his crushing, piano-driven ballads to his caustic rock pieces and eccentric spoken-word tracks, Waits always reflects things we can recognize from our own lives, even if we don’t happen to be lost hobos, wayward cowboys, ancient lovers, or barroom maniacs. Ultimately, his music is about the relationship between the longing we feel for authentic experiences and the peace we feel when we finally let that longing go.

Since 1973, Tom Waits has released 16 studio albums, beginning with Closing Time and ending with 2011’s Bad as Me. Almost all of those records are represented among the following 30 tracks, which should offer a solid overview of his many styles and personalities, as well as a compelling case for his status as one of America’s greatest—and most bizarre—musical figures.

30. “Way Down in the Hole” (Franks Wild Years, 1987)

On the surface, this is a religious song about keeping the devil at bay—though, knowing Waits, the devil could be any number of things. The music is excellent, its staccato saxophones and jazz-lounge bass mirroring the song’s sense of moral anxiety. The guitar solo is melodically unhinged; genius lies in its spastic gestures. Different versions of this song (including Waits’) were used as the theme song for HBO’s The Wire.

29. “Georgia Lee” (Mule Variations, 1999)

Recounting the devastating murder of Georgia Lee Moses and the questions it raised, this is one of Waits’ most deeply melancholic songs. For those who keep up with the news, “How can this happen?” is almost a daily question; this is that sentiment in song form. Fortunately, Waits’ sympathetic piano playing and singing guides us through.

28. “Hoist That Rag” (Real Gone, 2004)

“Hoist That Rag” contains characters from Herbert Asbury’s book The Gangs of New York, possible references to anti-war television (M*A*S*H) and literature (Alberto Vea’s Gods Go Begging), and pseudo-patriotic imagery (“hoist that rag”). Some say Real Gone is Waits’ most political album, and it’s hard to argue against that, with the record’s proximity to 9/11 and the Iraq War. The Waits-on-Waits-on-Waits layering of vocals in the chorus hits squarely in the gut.

27. “What’s He Building?” (Mule Variations, 1999)

Here is Tom Waits’ most interesting spoken-word track, a musty monologue by an inquisitive neighbor. The song’s spooky invasiveness is self-evident. Here’s what Waits had to say about it: “We’ve all become overly curious about our neighbors, and we all do believe, in the end, that we have a right to know what all of us are doing.” That’s a bad road to be on, to be sure, and it’s populated with tenants like these.

26. “Hell Broke Luce” (Bad As Me, 2011)

If Captain Beefheart had written and recorded a song while smoking crack, it would sound like this. It’s a bit ambiguous just who “Luce” is (and Waits has given multiple, conflicting explanations), but this remains a mournful tale of militaristic despair.

25. “Dirt in the Ground” (Bone Machine, 1992)

This is a relentlessly bleak song, and it’s also probably as close as Waits gets to falsetto. Between “I want to know am I the sky or a bird” and “We’re chained to the world and we all gotta pull,” it seems like he was going through a tough time when he wrote it. Bone Machine won a Grammy for Best Alternative Music Album, and with good reason.

24. “Johnsburg, Illinois” (Swordfishtrombones, 1983)

A sentimental ballad about Waits’ wife, Kathleen Brennan, “Johnsburg, Illinois” is one of his shortest songs. It works well as a 90-second track, though, because there’s really not much left to be said after starting a song with “She’s my only true love/She’s all that I think of/Look here in my wallet/That’s her.” The best things come in small packages.

23. “Lie to Me” (Orphans: Brawlers, Bawlers & Bastards, 2006)

Waits’ massive triple album, Orphans: Brawlers, Bawlers & Bastards, was full of explosive songs that ranged from hard rockers to quietly searing tearjerkers. The album’s very first track was possibly its most potent: The amped-up “Lie to Me” comes across as Jerry Lee Lewis-meets-Howlin’ Wolf, sung from the shadowy side of the bar.

22. “Ol’ ‘55” (Closing Time, 1973)

Closing Time was produced, engineered, and arranged by Jerry Yester (The Lovin’ Spoonful), which is probably a big part of why tracks like “Ol’ ‘55” have such a breezy, straightforward folk-rock feel. When read alone, its lyrics seem like a mutant song pieced together from Bruce Springsteen’s cutting-room floor. Most interesting and affecting are the track’s vocal harmonies, which Waits doesn’t use often.

21. “All the World Is Green” (Blood Money, 2002)

This endearing song was written for Act III of a production of Woyzeck, the incomplete 19th-century play about a soldier who murders his wife for leaving him. The “green” in the title seems to represent harmony with the natural world, but green also has a potential dark side: the color of money.

20. “Cold Cold Ground” (Franks Wild Years, 1987)

Just try to find a more lighthearted-sounding song about death. Despite sobering lyrics like “The piano is firewood/Times Square is a dream/I find we’ll lay down together/In the cold cold ground,” this song makes makes you want to dance, whether alone or with a loved one. Life is too short not to.

19. “Everything You Can Think Of Is True” (Alice, 2002)

This is a masterpiece of surrealist prose. Most of the album Alice was written for Robert Wilson’s stage adaptation of Alice in Wonderland, and it’s no surprise that this song fits the bill perfectly. Waits said of the project: “Alice is adult songs for children, or children’s songs for adults. It’s a maelstrom or fever-dream, a tone-poem, with torch songs and waltzes … an odyssey in dream and nonsense.”

18. “Tom Traubert’s Blues (Four Sheets to the Wind in Copenhagen)” (Small Change, 1976)

Based on Australian bush ballad “Waltzing Matilda” and taking as its content Waits’ treacherous relationship with alcohol, “Tom Traubert’s Blues (Four Sheets to the Wind in Copenhagen)” has an excess of melodic beauty and dark imagery (“I begged you to stab me/You tore my shirt open”). Legend has it that Waits bought a pint of rye and drank it out of a paper bag on Skid Row in L.A., an area with one of the country’s largest homeless populations, to get inspired to write this song.

17. “16 Shells from a Thirty-Ought Six” (Swordfishtrombones, 1983)

In a lot of ways, Swordfishtrombones was the record where Tom Waits became Tom Waits, at least in terms of the sounds he would be working through for the rest of his career. A major departure from the romantic, jazzy pop of Heartattack and Vine, “16 Shells from a Thirty-Ought Six” sounds instead like drunken, avant-garde blues on a factory floor, complete with Waits’ whiskey- and cigarette-soaked voice, a cacophony of percussion, and gritty guitar.

16. “Hold On” (Mule Variations, 1999)

This one is chock-full of good old American transience. Proceeding eastward from California to St. Louis, “Hold On” is a story that isn’t really a story—it’s more of an impressionistic assembly of images from the road, drawn together by the idea that, no matter what we’re doing, we’re all holding on to something. 

15. “Anywhere I Lay My Head” (Rain Dogs, 1985)

The final track of Rain Dogs, “Anywhere I Lay My Head” channels New Orleans funeral music in all its jazzy bombast and somber, polyphonic glory. Somehow its lyrics (“I don’t need anybody/Because I learned to be alone/And I say anywhere, anywhere, anywhere I lay my head, boys/I will call my home”) don’t feel defeatist at all. Rather, they’re the cherry on top of Waits’ roaming, experimental masterpiece.

14. “On the Nickel” (Heartattack and Vine, 1980)

This is it: Waits’ grandest tribute to the hobos and downtrodden, those who have truly fallen through the cracks of society. “On the Nickel” has a tremendous pathos that rivals anything Waits has written. Take, for example: “So what becomes of all the little boys who run away from home?/The world just keeps getting bigger once you get out on your own/So here’s to all the little boys, the sandman takes you where/You’re sleepin’ with a pillowman on the nickel over there.”

13. “The Piano Has Been Drinking (Not Me)” (Small Change, 1976)

In this one, Waits plays a wasted barroom beat poet delivering an impassioned lecture about his altered state. Full of crazy imagery (“‘Cause the bouncer is a Sumo wrestler/Cream-puff casper milquetoast”) and funny observations (“And you can’t find your waitress/With a Geiger counter”), this song makes your neighborhood bar seem a little more normal.

12. “I Hope That I Don’t Fall In Love With You” (Closing Time, 1973)

“I Hope That I Don’t Fall In Love With You” is a beloved fan favorite, which is understandable—beyond the ultra-palatable ‘60s folk-pop feel, this packs a lot of emotional depth. A vulnerable guy contemplates saddling up next to a lonesome woman at a bar, but his fear of loss prevents him from doing it. He’s been hurt before. The longer he thinks about it, the more he falls in love with the idea of her, and as he closes in on the courage to strike up a conversation, he finds that it’s last call for drinks and she’s gone home.

11. “Alice” (Alice, 2002)

It’s easy to take Alice for granted, and many rank it somewhere in the middle of Waits’ oeuvre, but it’s probably his most beautifully composed album of the 21st century so far. In the title track, breathy saxophones nudge against wintery brushed snare; calm piano supports what sounds like hushed vibraphone. It’s a mysterious, misty classic.

10. “Jockey Full of Bourbon” (Rain Dogs, 1985)

It’s impossible to hear this song without thinking of how it’s used in Down by Law, Jim Jarmusch’s incredibly funny movie about three tragic dudes (played by John Lurie, Roberto Benigni, and Waits himself) making an impossibly humid journey from the streets of New Orleans to the swamps of rural Louisiana. This grimy, dirty-feeling song haunts every frame of that film with its whispered legend of a pathetic, wasted hero and his broken gun.

9. “Come On Up to the House” (Mule Variations, 1999)

This is either one of Waits’ greatest self-help anthems or one of his most gripping treatises on dying. As Nietzsche might say, this is about the catharsis of tragedy. “The house” is necessarily ambiguous—the song is just about the idea of accepting despair and letting go of it. It’s a final song of sorts for many of Waits’ characters, from the lovesick loners to the desolate train-hoppers, those “singin’ lead soprano in a junkman’s choir.” There’s a reason it’s the last track of the goodbye-filled Mule Variations, which is as good an argument as any that it may be about something … beyond.

8. “Christmas Card from a Hooker in Minneapolis” (Blue Valentine, 1978)

There’s truly no tale that Tom Waits won’t tell. “Christmas Card from a Hooker in Minneapolis” is exactly what it sounds like, its title nearly a six-word Hemingway story in itself. As the Christmas card is read, we learn quite a bit about the woman’s sad story, and after the song’s final, sobering twist, we’re basically prepared to send her some money ourselves.

7. “Time” (Rain Dogs, 1985)

A gentle ode to the act of self-overcoming, “Time” is one of Waits’ most touching ballads. It’s a great example of his incredible ability to orchestrate a song to perfectly match the mood of the lyrics; the slowly cascading guitars and accordion—as well as the lack of percussion—give the song a decidedly timeless pacing.

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

It’s disorienting how little conflict exists here. Probably the most chill pregame/hype song ever written, it’s just about a guy going out—on Saturday night, of course—hoping that he’ll have a good time. Waits is a crack shot with narrative, but he’s also a master of mood: the joyriding cars in the background, the carefree guitars, and the (barely) shuffling percussion absolutely make this song.

5. “Martha” (Closing Time, 1973)

An entire novel transpires in the four-and-a-half minutes of “Martha,” but its genius lies in what’s not there. Tom Frost calls Martha after 40 years of not talking; they used to be in a relationship (“And those were the days of roses/of poetry and prose”) but somehow lost touch. Why, exactly, did they break up? He says he was impulsive, but he doesn’t reveal enough for us to know anything for sure. Do they get back together? Well, that’s really up to you.

4. “Kentucky Avenue” (Blue Valentine, 1978)

“Kentucky Avenue” is a “Desolation Row”-level epic, told from the perspective of a child. Listen as Waits remembers the wild and weird events from the street he grew up on. This is a roaming fantasia that should feel familiar to anyone who spent a lot of time outside as a child.

3. “Jersey Girl” (Heartattack and Vine, 1980)

This is the best Bruce Springsteen song that Springsteen never wrote, and Springsteen himself knows it—he performed it at countless concerts in the ‘80s and ‘90s. Waits’ gripping love song evokes a breezy, simpler time with its pictures of carnivals and boardwalks, as well as its “sha la la” refrain. It’s unmistakably Waits in its constant threat to overflow with passion.

2. “Downtown Train” (Rain Dogs, 1985)

From its shimmering electric-guitar lyricism to its perfectly conjured late-night New York imagery, “Downtown Train” is Waits’ most coherent statement of longing. It’s also probably his most straightforward rock song, and one that gives the experimental, bluesy Rain Dogs its head-bobbing anchor. This is a beautifully vulnerable quest for contact that sees Waits’ gravelly yawp at its most affecting.

1. “Take It With Me” (Mule Variations, 1999)

This song turns it all upside down, trading in Waits’ typical portraits of yearning and rambunctious vagrancy for transcendent images of love and goodness. “Take It With Me” is about a man on the other side of love, looking back at his life without sadness or regret. The calm centerpiece of an album full of bombast, violence, and weighty American sadness, this stripped-down reverie for voice, piano, and bass finds solace through its gentile thesis. Indeed, it proves that Waits has never needed more than 88 keys and an open heart.

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