Tom Waits' Best Song From Each Of His Studio Albums

Feature Photo: English: Photograph by Greg Gorman, according to the Tom Waits Library. Published by Asylum/Herb Cohen Management., Public domain, via Wikimedia Commons

I was 15 years old in 1976 when a friend of mine played me the song “The Piano Has Been Drinking.” The voice scared me at first. I laughed at the title, but upon listening a little deeper, I heard something I had never heard before in pop music. I instantly dove into his material, buying every album that Waits had released up to that point. It would be easy to argue that most music fans who discovered Tom Waits in the ’70s have stuck with him throughout his entire career, buying every new album up through his most recent studio album, 2011’s Bad As Me. It took me a few months to write this one because I wanted to pay proper respect to an artist who has brought me, and millions of others, great joy. The intention of this article is to introduce people to his music who have never heard him before and, as with every article we publish here, to celebrate alongside those who have traveled the road with us. Waits returned with new original music in 2026 on “Boots on the Ground,” a collaboration with Massive Attack, and the spoken-word track “The Fly,” but Bad As Me remains his most recent studio album.

While many artists will release music in the same style for their entire career, Tom Waits has redefined what it means to be a songwriter, storyteller, and sonic innovator. Born in Pomona, California, in 1949, Waits emerged from the smoky bars and dimly lit clubs of Los Angeles in the early 1970s, a scrappy, soulful poet whose gravelly voice and piano-driven ballads spoke of beatnik romance, seedy dives, and the lives of the down-and-out. His debut album, Closing Time (1973), introduced a young Waits who seemed cut from the same cloth as the jazz and folk singers of old, with a sound that blended the melancholic beauty of late-night jazz with the lyrical candor of a Dylan-esque singer-songwriter.

However, it wasn’t long before Waits began to challenge the conventions of his early style. By the time he released Swordfishtrombones in 1983, the transformation was unmistakable: the sentimental crooner of “Martha” and “Ol’ 55” had given way to a wild-eyed, whiskey-soaked carnival barker whose songs were populated by strange characters and underscored by the clang of junkyard percussion and the wheeze of circus organs. This era marked the beginning of Waits’ most experimental and influential period, where he began collaborating with his wife, Kathleen Brennan, who encouraged him to embrace his most avant-garde impulses. Albums like Rain Dogs (1985) and Franks Wild Years (1987) broke new ground with their eclectic soundscapes, blending blues, vaudeville, cabaret, and industrial noise to create something entirely unique—music that was both rooted in tradition and daringly forward-looking.

The 1990s and 2000s saw Waits continue to expand his creative palette, incorporating elements of theater, spoken word, and found sounds into his work. With albums like Bone Machine (1992) and Mule Variations (1999), Waits cemented his reputation as a musical alchemist, equally comfortable with a raw, percussive stomp like “Hoist That Rag” from Real Gone (2004) or the stark, haunting minimalism of “Alice” from Alice (2002). His most recent studio album, Bad as Me (2011), finds Waits still at the peak of his powers, blending the rough-hewn grit of his earlier work with a newfound clarity and directness, reflecting a lifetime spent pushing against the boundaries of his art.

This article will explore the best song from each of Tom Waits’ studio albums, charting his incredible evolution from a gifted young songwriter steeped in the traditions of jazz and folk to a fearless innovator who has redefined the possibilities of popular music. With each album, Waits has taken listeners on a journey into the unknown, and this selection highlights the standout tracks that best capture the essence of his ever-changing sound and vision. From the tender ballads of his early years to the audacious experiments of his later career, these songs illustrate why Tom Waits remains one of the most compelling and unpredictable artists of our time.

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

Released March 6, 1973

Runner Up: “Martha”

1973 was a special year in music, as it marked the debuts of three of the most influential and beloved musical artists of all time: Tom Waits, Billy Joel, and Bruce Springsteen, all of whom released their debut albums that year. This is not the Tom Waits many people first discovered in the 1980s; on Closing Time, what you get is a collection of piano-led songs with sparse arrangements that are simply stunning. “I Hope That I Don’t Fall In Love With You” is an intimate ballad that unfolds like a late-night confession, capturing a man caught between the desire to connect and the fear of heartbreak. Its directness and sincerity make it one of the purest expressions of the love, loss, and longing that would remain central to Waits’ songwriting. “Martha,” the runner-up, is equally poignant, but the raw vulnerability and immediacy of “I Hope That I Don’t Fall In Love With You” make it our pick from his debut.

“A New Coat Of Paint” – The Heart of Saturday Night (1974)

Released October 15, 1974

Runner Up: “Depot, Depot”

“A New Coat Of Paint,” the opening track from Tom Waits’ 1974 album The Heart of Saturday Night, sets the tone for a record that straddles the line between beatnik jazz and barroom blues. Recorded at Wally Heider Studios in Hollywood and produced by Bones Howe, the song finds Waits in a reflective yet hopeful mood, proposing a fresh start despite life’s wear and tear. Its rolling piano and jazz-blues feel give the track a lively, late-night pulse, while the central image of putting a new coat of paint on a lonesome old town turns renewal into something both romantic and temporary. “Depot, Depot,” the runner-up, shares the album’s sense of movement and restlessness, but “A New Coat Of Paint” wins out for its combination of lyrical wit, musical sophistication, and emotional warmth.

“Big Joe And Phantom 309” – Nighthawks at the Diner (1975)

Released October 21, 1975

Runner Up: “Warm Beer And Cold Women”

“Big Joe And Phantom 309” is our pick from Tom Waits’ 1975 Nighthawks at the Diner, a double album of new material recorded live before a small invited audience at the Record Plant in Los Angeles over four sessions. Produced by Bones Howe, the record captures the atmosphere of Waits’ early club performances, where storytelling and music were inseparable. Waits’ version of Tommy Faile’s “Big Joe and Phantom 309” unfolds like a roadside ghost story, following a hitchhiker who discovers that the trucker who picked him up is the spirit of a man who died saving a busload of children. Waits delivers the tale with humor, empathy, and an eerie sense of the open road. “Warm Beer And Cold Women” is a great companion piece, but the cinematic storytelling and supernatural atmosphere of “Big Joe And Phantom 309” make it the standout.

“Tom Traubert’s Blues” – Small Change (1976)

Released September 21, 1976

Runner Up: “The Piano Has Been Drinking (Not Me)”

“Tom Traubert’s Blues,” from Tom Waits’ 1976 album Small Change, stands as one of the most evocative and haunting songs in his catalog. Recorded at Wally Heider Studios in Hollywood and produced by Bones Howe, the album surrounds Waits with a sympathetic jazz setting that gives his voice and storytelling room to breathe. The song borrows the refrain of the Australian folk song “Waltzing Matilda” and transforms it into a mournful lament for a wounded, displaced narrator moving through a broken nocturnal world. Its piano-led arrangement and weary vocal performance give the track a tremendous emotional gravity. “The Piano Has Been Drinking (Not Me)” provides the album’s sardonic, absurdist counterweight, but “Tom Traubert’s Blues” captures the full depth of Waits’ early artistry and remains one of the defining songs of his career.

“Muriel” – Foreign Affairs (1977)

Released September 13, 1977

Runner Up: “Burma Shave”

“Muriel,” from Tom Waits’ 1977 album Foreign Affairs, is a poignant exploration of lost love and the ghosts of a past that refuses to disappear. Recorded at Filmways/Heider Recording in Hollywood and produced by Bones Howe, the album continues the nocturnal jazz mood of Waits’ earlier records while expanding into more cinematic arrangements. “Muriel” is built around the simple sadness of a man whose surroundings seem emptied out by the absence of the woman he loved; every club, street, and familiar place becomes another reminder of what is gone. The orchestral color heightens the melancholy without overwhelming the song’s intimate core. “Burma Shave,” the runner-up, takes its characters out on the road in search of escape, but “Muriel” stays closer to home and turns that stillness into something painfully universal.

“Christmas Card From A Hooker In Minneapolis” – Blue Valentine (1978)

Released September 5, 1978

Runner Up: “Romeo Is Bleeding”

“Christmas Card From A Hooker In Minneapolis,” from Tom Waits’ 1978 album Blue Valentine, is one of the clearest examples of his ability to turn a character sketch into something deeply human. Produced by Bones Howe, the song is framed as a letter from a woman who initially presents an optimistic picture of her life before gradually revealing that much of what she has written is untrue and that she needs help. That slow collapse of the façade is what gives the song its emotional force: the listener moves from hope to heartbreak without the narrator ever becoming a caricature. The sparse setting leaves Waits’ piano and weathered voice at the center of the story. “Romeo Is Bleeding” is the more kinetic, noir-styled runner-up, but “Christmas Card” is the album’s most devastating piece of character-driven storytelling.

“Ruby’s Arms” – Heartattack and Vine (1980)

Released September 9, 1980

Runner Up: “Jersey Girl”

“Ruby’s Arms,” the closing track from Tom Waits’ 1980 album Heartattack and Vine, is a deeply moving ballad about quietly leaving a lover and knowing that the goodbye is final. Recorded at Filmways/Heider Recording in Hollywood and produced by Bones Howe, the album was the last Waits studio record Howe produced before Waits moved into the radically different sound of Swordfishtrombones. “Ruby’s Arms” remains rooted in the classic ballad tradition, with piano and orchestral color supporting a lyric filled with small physical details that make the departure feel painfully real. “Jersey Girl,” the runner-up, offers a warmer and more hopeful view of love and would later become closely associated with Bruce Springsteen, but “Ruby’s Arms” carries an intimacy and sense of finality that make it our choice from the album.

“In The Neighborhood” – Swordfishtrombones (1983)

Released September 1, 1983

Runner Up: “Shore Leave”

“In The Neighborhood” is a vivid portrait of a rough-and-tumble community and one of the songs that best captures the radical change Tom Waits made on Swordfishtrombones. By 1983, the piano-bar romantic of the 1970s had opened the door to junkyard percussion, unusual horns, fractured rhythms, and imagery that could turn an ordinary street into a miniature theater. The song’s brass-band feel carries both celebration and funeral-procession sadness as Waits moves through scenes of dogs, delivery trucks, drifters, and neighborhood routines. “Shore Leave,” the runner-up, pushes even further into dislocation and surreal travel imagery, but “In The Neighborhood” is the clearer statement of Waits’ new artistic freedom. It sounds rooted in old American musical traditions while also announcing that from this point forward, his records would follow their own rules.

“Downtown Train” – Rain Dogs (1985)

Released September 30, 1985

Runner Up: “Time”

“Downtown Train,” from Tom Waits’ 1985 album Rain Dogs, stands out as one of his most accessible and emotionally direct songs. Produced by Waits during the extraordinary creative period that followed Swordfishtrombones, Rain Dogs moves through blues, folk, rock, cabaret, and experimental textures while remaining unmistakably his own. “Downtown Train” uses a more conventional rock structure than much of the album, but the setting is pure Waits: city nights, trains, distance, longing, and the feeling of watching life move past while hoping someone will finally look your way. Its strong melody helped make the song one of Waits’ most widely covered compositions, including Rod Stewart’s hit version. “Time,” the runner-up, is quieter and more reflective, but “Downtown Train” wins for the way it combines immediacy with the strange romantic atmosphere of Rain Dogs.

“Way Down In The Hole” – Franks Wild Years (1987)

Released August 17, 1987

Runner Up: “Hang On St. Christopher”

“Way Down In The Hole,” from Tom Waits’ 1987 album Franks Wild Years, is a gospel-blues warning about temptation, faith, sin, and the constant need to keep the devil at bay. Created during the theatrical period that grew out of the stage work Waits developed with Kathleen Brennan, the album pushes the strange instrumentation and dramatic character of Swordfishtrombones and Rain Dogs into an even more theatrical setting. “Way Down In The Hole” rides a deep, spare groove while Waits delivers the lyric like a street-corner sermon. The song later reached a much wider audience through The Wire, which used different recordings of it as the series theme. “Hang On St. Christopher” is a terrific runner-up with its own urgent, rattling momentum, but “Way Down In The Hole” has become one of the most durable songs of Waits’ experimental middle period.

“I Don’t Wanna Grow Up” – Bone Machine (1992)

Released September 8, 1992

Runner Up: “Murder In The Red Barn”

“I Don’t Wanna Grow Up,” from Tom Waits’ 1992 album Bone Machine, is a rebellious refusal of adulthood delivered inside one of the rawest records he ever made. Recorded at Prairie Sun Recording Studios in Cotati, California, the album embraces percussion, distorted guitars, skeletal arrangements, and songs preoccupied with mortality, decay, fear, and survival. Against that setting, “I Don’t Wanna Grow Up” is almost disarmingly simple: its childlike refrain collides with an adult’s knowledge of disappointment, responsibility, and the things that can go wrong. The stripped-down guitar and Waits’ rough vocal give it the feeling of a nursery rhyme dragged through a junkyard. “Murder In The Red Barn,” the runner-up, turns toward gothic narrative and rural menace, but “I Don’t Wanna Grow Up” is more universal and captures Bone Machine’s mixture of humor, dread, and defiance in a single unforgettable song.

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“The Black Rider” – The Black Rider (1993)

Released November 2, 1993

Runner Up: “T’ Ain’t No Sin”

“The Black Rider,” the title track from Tom Waits’ 1993 album The Black Rider, takes his theatrical instincts into a world of German cabaret, dark comedy, distorted carnival music, and Faustian dread. The project grew from Waits’ collaboration with director Robert Wilson and writer William S. Burroughs on the stage work of the same name, drawing on the old Freischütz legend of magic bullets and fatal bargains. The title track serves as a perfect doorway into that haunted world, with Waits acting as sinister guide while dissonant horns and odd instrumental textures make the music feel unstable beneath him. “T’ Ain’t No Sin,” the runner-up, brings black humor to the record through a much older popular song, but “The Black Rider” is the piece that most completely captures the album’s grotesque theatrical atmosphere and its place in Waits’ continuing reinvention.

“What’s He Building?” – Mule Variations (1999)

Released April 16, 1999

Runner Up: “Get Behind the Mule”

“What’s He Building?” from Tom Waits’ 1999 album Mule Variations is one of the most unsettling pieces in his catalog. Recorded at Prairie Sun Recording Studios in Cotati, California, the album brought Waits back with a mixture of blues, folk, gospel, strange percussion, and narrative experimentation after a six-year gap between studio albums. “What’s He Building?” is essentially spoken-word audio theater: Waits becomes a suspicious neighbor obsessing over the unexplained noises and habits of the man next door while creaks, bangs, and other sounds build an atmosphere of comic paranoia. There is no need for a traditional chorus because the tension comes from the narrator’s imagination and the possibility that he may be far stranger than the person he is watching. “Get Behind the Mule” is the swampy, hypnotic runner-up, but “What’s He Building?” is the album’s boldest example of Waits turning storytelling itself into music.

“Everything You Can Think” – Alice (2002)

Released May 7, 2002

Runner Up: “Alice”

“Everything You Can Think,” from Tom Waits’ 2002 album Alice, captures the surreal, dreamlike quality that runs through the entire record. The songs originated in Waits and Kathleen Brennan’s work for Robert Wilson’s 1992 stage production inspired by Lewis Carroll and Alice Liddell, then were recorded and released a decade later. The album moves between fragile chamber music, cabaret, jazz, and unsettling experimental textures, and “Everything You Can Think” embraces the strangest side of that world. Its hypnotic repetition and impossible imagery create the feeling of entering a place where logic no longer applies. The title track “Alice,” our runner-up, is more melodic and openly melancholy, but “Everything You Can Think” better represents the album’s willingness to make beauty and unease exist side by side. It is one of the clearest examples of Waits using music as a doorway into a fully imagined theatrical universe.

“God’s Away on Business” – Blood Money (2002)

Released May 7, 2002

Runner Up: “Everything Goes to Hell”

“God’s Away on Business,” from Tom Waits’ 2002 album Blood Money, is a ferocious portrait of a world in moral collapse. Written in connection with Waits, Kathleen Brennan, and Robert Wilson’s work on Woyzeck, the album is harsher and more earthbound than the dreamlike Alice, even though the two records arrived on the same day. “God’s Away on Business” moves on a lurching, ominous rhythm with dark horns and Waits’ voice at its most menacing, turning social corruption, violence, greed, and absurdity into a kind of broken cabaret. The track’s theatricality never softens its anger; it sounds like a sermon delivered after the preacher has lost faith in the congregation. “Everything Goes to Hell,” the runner-up, shares the record’s black humor and fatalism, but “God’s Away on Business” has the visceral force that makes it one of the defining songs of Waits’ later catalog.

“Hoist That Rag” – Real Gone (2004)

Released October 5, 2004

Runner Up: “Top Of The Hill”

“Hoist That Rag,” from Tom Waits’ 2004 album Real Gone, dives into a raw, percussive, politically charged sound that pushed his music in another new direction. Written and produced by Waits and Kathleen Brennan, Real Gone famously abandoned piano and built much of its character from mouth percussion, distorted guitars, bass, drums, and rough rhythmic textures. “Hoist That Rag” is driven by Marc Ribot’s cutting guitar and a relentless groove that gives the song the feeling of a march through a damaged landscape. Its imagery is violent and unsettled, and the repeated title phrase lands like a rallying cry whose meaning is deliberately uneasy. “Top Of The Hill,” the runner-up, announces the record’s experimental intent immediately, but “Hoist That Rag” is the song where the anger, rhythm, guitar, and strange beauty of Real Gone come together most powerfully.

“Bad as Me” – Bad as Me (2011)

Released October 21, 2011

Runner Up: “Pay Me”

“Bad as Me,” the title track from Tom Waits’ 2011 album Bad as Me, is a snarling, swaggering declaration that shows how easily Waits can make his entire musical history feel immediate again. Produced by Waits and Kathleen Brennan, the album was his first collection of entirely new studio material in seven years and brought together blues, rock, jazz, balladry, and the rough textures that had defined his later work. The title track is compact and direct, driven by biting guitar, a tight rhythm section, and Waits’ gleefully abrasive vocal. Its central idea turns compatibility into something mischievous: two people recognizing the same trouble in each other. “Pay Me,” the runner-up, offers the record’s more tender and reflective side, but “Bad as Me” has the fierce energy and dark humor that make it the strongest closing selection for an album-by-album journey through Waits’ studio career.