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 everywhereâfrom Tin Pan Alley, Harry Partch, and Bob Dylan to Raymond Carver, Jack Kerouac, and Charles Bukowski.
Waitsâ sound is all over the mapâhe 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 itâs always on the verge of coming together, yet it has a cohesion and consistency that makes it immediately recognizable. Then thereâs his voice, about which thereâs half a century of vibrant metaphors and descriptions.
What really binds together Waitsâ 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 isâthroughout 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 donât 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 2011âs 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 Americaâs greatestâand most bizarreâmusical figures.
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30. âWay Down in the Holeâ (Franks Wild Years, 1987)
On the surface, this is a religious song about keeping the devil at bayâthough, knowing Waits, the devil could be any number of things. The music is excellent, its staccato saxophones and jazz-lounge bass mirroring the songâs sense of moral anxiety. The guitar solo is melodically unhinged; genius lies in its spastic gestures. Different versions of this song (including Waitsâ) were used as the theme song for HBOâs The Wire.
29. âGeorgia Leeâ (Mule Variations, 1999)
Recounting the devastating murder of Georgia Lee Moses and the questions it raised, this is one of Waitsâ most deeply melancholic songs. For those who keep up with the news, âHow can this happen?â is almost a daily question; this is that sentiment in song form. Fortunately, Waitsâ sympathetic piano playing and singing guides us through.
28. âHoist That Ragâ (Real Gone, 2004)
âHoist That Ragâ contains characters from Herbert Asburyâs book The Gangs of New York, possible references to anti-war television (M*A*S*H) and literature (Alberto Veaâs Gods Go Begging), and pseudo-patriotic imagery (âhoist that ragâ). Some say Real Gone is Waitsâ most political album, and itâs hard to argue against that, with the recordâs 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. âWhatâs He Building?â (Mule Variations, 1999)
Here is Tom Waitsâ most interesting spoken-word track, a musty monologue by an inquisitive neighbor. The songâs spooky invasiveness is self-evident. Hereâs what Waits had to say about it: âWeâve 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.â Thatâs a bad road to be on, to be sure, and itâs populated with tenants like these.
26. âHell Broke Luceâ (Bad As Me, 2011)
If Captain Beefheart had written and recorded a song while smoking crack, it would sound like this. Itâs a bit ambiguous just who âLuceâ is (and Waits has given multiple, conflicting explanations), but this remains a mournful tale of militaristic despair.
25. âDirt in the Groundâ (Bone Machine, 1992)
This is a relentlessly bleak song, and itâs also probably as close as Waits gets to falsetto. Between âI want to know am I the sky or a birdâ and âWeâre chained to the world and we all gotta pull,â 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. âJohnsburg, Illinoisâ (Swordfishtrombones, 1983)
A sentimental ballad about Waitsâ wife, Kathleen Brennan, âJohnsburg, Illinoisâ is one of his shortest songs. It works well as a 90-second track, though, because thereâs really not much left to be said after starting a song with âSheâs my only true love/Sheâs all that I think of/Look here in my wallet/Thatâs her.â The best things come in small packages.
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23. âLie to Meâ (Orphans: Brawlers, Bawlers & Bastards, 2006)
Waitsâ massive triple album, Orphans: Brawlers, Bawlers & Bastards, was full of explosive songs that ranged from hard rockers to quietly searing tearjerkers. The albumâs very first track was possibly its most potent: The amped-up âLie to Meâ comes across as Jerry Lee Lewis-meets-Howlinâ Wolf, sung from the shadowy side of the bar.
22. âOlâ â55â (Closing Time, 1973)
Closing Time was produced, engineered, and arranged by Jerry Yester (The Lovinâ Spoonful), which is probably a big part of why tracks like âOlâ â55â have such a breezy, straightforward folk-rock feel. When read alone, its lyrics seem like a mutant song pieced together from Bruce Springsteenâs cutting-room floor. Most interesting and affecting are the trackâs vocal harmonies, which Waits doesnât use often.
21. âAll the World Is Greenâ (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 âgreenâ in the title seems to represent harmony with the natural world, but green also has a potential dark side: the color of money.
20. âCold Cold Groundâ (Franks Wild Years, 1987)
Just try to find a more lighthearted-sounding song about death. Despite sobering lyrics like âThe piano is firewood/Times Square is a dream/I find weâll lay down together/In the cold cold ground,â this song makes makes you want to dance, whether alone or with a loved one. Life is too short not to.
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19. âEverything You Can Think Of Is Trueâ (Alice, 2002)
This is a masterpiece of surrealist prose. Most of the album Alice was written for Robert Wilsonâs stage adaptation of Alice in Wonderland, and itâs no surprise that this song fits the bill perfectly. Waits said of the project: âAlice is adult songs for children, or childrenâs songs for adults. Itâs a maelstrom or fever-dream, a tone-poem, with torch songs and waltzes ⊠an odyssey in dream and nonsense.â
18. âTom Traubertâs Blues (Four Sheets to the Wind in Copenhagen)â (Small Change, 1976)
Based on Australian bush ballad âWaltzing Matildaâ and taking as its content Waitsâ treacherous relationship with alcohol, âTom Traubertâs Blues (Four Sheets to the Wind in Copenhagen)â has an excess of melodic beauty and dark imagery (âI begged you to stab me/You tore my shirt openâ). 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. â16 Shells from a Thirty-Ought Sixâ (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, â16 Shells from a Thirty-Ought Sixâ sounds instead like drunken, avant-garde blues on a factory floor, complete with Waitsâ whiskey- and cigarette-soaked voice, a cacophony of percussion, and gritty guitar.
16. âHold Onâ (Mule Variations, 1999)
This one is chock-full of good old American transience. Proceeding eastward from California to St. Louis, âHold Onâ is a story that isnât really a storyâitâs more of an impressionistic assembly of images from the road, drawn together by the idea that, no matter what weâre doing, we’re all holding on to something.Â
15. âAnywhere I Lay My Headâ (Rain Dogs, 1985)
The final track of Rain Dogs, âAnywhere I Lay My Headâ channels New Orleans funeral music in all its jazzy bombast and somber, polyphonic glory. Somehow its lyrics (âI donât need anybody/Because I learned to be alone/And I say anywhere, anywhere, anywhere I lay my head, boys/I will call my homeâ) donât feel defeatist at all. Rather, theyâre the cherry on top of Waitsâ roaming, experimental masterpiece.
14. âOn the Nickelâ (Heartattack and Vine, 1980)
This is it: Waitsâ grandest tribute to the hobos and downtrodden, those who have truly fallen through the cracks of society. âOn the Nickelâ has a tremendous pathos that rivals anything Waits has written. Take, for example: âSo 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 hereâs to all the little boys, the sandman takes you where/Youâre sleepinâ with a pillowman on the nickel over there.â
13. âThe Piano Has Been Drinking (Not Me)â (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 (ââCause the bouncer is a Sumo wrestler/Cream-puff casper milquetoastâ) and funny observations (âAnd you canât find your waitress/With a Geiger counterâ), this song makes your neighborhood bar seem a little more normal.
12. âI Hope That I Donât Fall In Love With Youâ (Closing Time, 1973)
âI Hope That I Donât Fall In Love With Youâ is a beloved fan favorite, which is understandableâbeyond the ultra-palatable â60s 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. Heâs 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 itâs last call for drinks and sheâs gone home.
11. âAliceâ (Alice, 2002)
Itâs easy to take Alice for granted, and many rank it somewhere in the middle of Waitsâ oeuvre, but itâs 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. Itâs a mysterious, misty classic.
10. âJockey Full of Bourbonâ (Rain Dogs, 1985)
Itâs impossible to hear this song without thinking of how itâs used in Down by Law, Jim Jarmuschâs 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. âCome On Up to the Houseâ (Mule Variations, 1999)
This is either one of Waitsâ greatest self-help anthems or one of his most gripping treatises on dying. As Nietzsche might say, this is about the catharsis of tragedy. âThe houseâ is necessarily ambiguousâthe song is just about the idea of accepting despair and letting go of it. Itâs a final song of sorts for many of Waitsâ characters, from the lovesick loners to the desolate train-hoppers, those âsinginâ lead soprano in a junkmanâs choir.â Thereâs a reason itâs 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. âChristmas Card from a Hooker in Minneapolisâ (Blue Valentine, 1978)
Thereâs truly no tale that Tom Waits wonât tell. âChristmas Card from a Hooker in Minneapolisâ 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 womanâs sad story, and after the songâs final, sobering twist, weâre basically prepared to send her some money ourselves.
7. âTimeâ (Rain Dogs, 1985)
A gentle ode to the act of self-overcoming, âTimeâ is one of Waitsâ most touching ballads. Itâs a great example of his incredible ability to orchestrate a song to perfectly match the mood of the lyrics; the slowly cascading guitars and accordionâas well as the lack of percussionâgive the song a decidedly timeless pacing.
6. â(Looking For) The Heart of Saturday Nightâ (The Heart of Saturday Night, 1974)
Itâs disorienting how little conflict exists here. Probably the most chill pregame/hype song ever written, itâs just about a guy going outâon Saturday night, of courseâhoping that heâll have a good time. Waits is a crack shot with narrative, but heâs also a master of mood: the joyriding cars in the background, the carefree guitars, and the (barely) shuffling percussion absolutely make this song.
5. âMarthaâ (Closing Time, 1973)
An entire novel transpires in the four-and-a-half minutes of âMartha,â but its genius lies in whatâs not there. Tom Frost calls Martha after 40 years of not talking; they used to be in a relationship (âAnd those were the days of roses/of poetry and proseâ) but somehow lost touch. Why, exactly, did they break up? He says he was impulsive, but he doesnât reveal enough for us to know anything for sure. Do they get back together? Well, thatâs really up to you.
4. âKentucky Avenueâ (Blue Valentine, 1978)
âKentucky Avenueâ is a âDesolation Rowâ-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. âJersey Girlâ (Heartattack and Vine, 1980)
This is the best Bruce Springsteen song that Springsteen never wrote, and Springsteen himself knows itâhe performed it at countless concerts in the â80s and â90s. Waitsâ gripping love song evokes a breezy, simpler time with its pictures of carnivals and boardwalks, as well as its âsha la laâ refrain. Itâs unmistakably Waits in its constant threat to overflow with passion.
2. âDowntown Trainâ (Rain Dogs, 1985)
From its shimmering electric-guitar lyricism to its perfectly conjured late-night New York imagery, âDowntown Trainâ is Waitsâ most coherent statement of longing. Itâs 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 Waitsâ gravelly yawp at its most affecting.
1. âTake It With Meâ (Mule Variations, 1999)
This song turns it all upside down, trading in Waitsâ typical portraits of yearning and rambunctious vagrancy for transcendent images of love and goodness. âTake It With Meâ 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.