Tom Waits’ Best Song From Each Of His Studio Albums

“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; you won’t hear any of the distinctive instrumentation or the howling vocals that came to define albums like Swordfishtrombones, Bone Machine, and Rain Dogs. On Tom Waits’ debut album, what you get is a collection of songs performed on piano with sparse arrangements that are simply stunning. There are many Tom Waits fans who prefer this style, which lasted for a handful of albums.

“I Hope That I Don’t Fall In Love With You” is an intimate ballad that unfolds like a late-night confession, capturing the internal dialogue of a man hesitant to surrender to his emotions. From the opening line, “Well, I hope that I don’t fall in love with you, ’cause falling in love just makes me blue,” Waits sets the stage for a narrative grounded in both self-awareness and doubt. The song’s simple chord progression and sparse instrumentation highlight the tension in the lyrics as the narrator wrestles with the desire to connect and the fear of inevitable heartbreak. Each verse draws the listener deeper into the dimly lit barroom, where a chance encounter turns into a profound meditation on loneliness and longing.

While Closing Time is often remembered for its quieter, more reflective moments, “I Hope That I Don’t Fall In Love With You” stands out for its directness and sincerity. Unlike later works such as “Invitation to the Blues” from The Heart of Saturday Night, which paints a cinematic scene full of characters and vivid details, this song relies on a more straightforward narrative. The track’s emotional impact lies in its simplicity—the way it captures a universal experience with just a few lines. The juxtaposition of hope and hesitation, love and loss, is a theme that would become central to Waits’ songwriting in subsequent albums, such as Small Change and Blue Valentine, but it finds one of its purest expressions here.

Although “I Hope That I Don’t Fall In Love With You” is the best song on Closing Time, “Martha,” the album’s runner-up, is equally poignant. In “Martha,” Waits explores a similar theme of lost love, but through the lens of an older man calling his former sweetheart after decades apart. Where “I Hope That I Don’t Fall In Love With You” captures the hesitation and immediacy of a nascent romance, “Martha” offers a heartbreaking reflection on what might have been, making it a natural companion piece on the album. Both songs highlight Waits’ knack for telling emotionally resonant stories, but “I Hope That I Don’t Fall In Love With You” edges out its counterpart for its ability to distill the complexity of human emotion into a deceptively simple melody and lyric.

In the context of this article, “I Hope That I Don’t Fall In Love With You” represents the pinnacle of Waits’ early folk-jazz period, where his lyricism and musicality were most accessible and direct. While “Martha” provides a glimpse into the regret and nostalgia that Waits would continue to explore throughout his career, the raw vulnerability and immediacy of “I Hope That I Don’t Fall In Love With You” make it the standout track from his debut—setting the stage for the many tales of love, loss, and longing that would follow.

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

Released October 15, 1974

Runner Up: “Depot Depot”

“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, offering a sly wink at life’s rougher edges while proposing a fresh start. With Mike Melvoin on piano, Jim Hughart on bass, and John Seiter on drums, the song captures the raw, late-night energy that defines much of Waits’ early work. It is both an invitation and a declaration, a call to renew and refresh despite the wear and tear of the years.

Lyrically, “New Coat of Paint” is a masterclass in metaphor and wordplay. The idea of slapping a “new coat of paint on this lonesome old town” reflects the desire for rejuvenation, not just of the environment but also of the human spirit. The lyrics invite a partner to embrace life anew: “We’ll wear a new look tonight in a romantic way,” suggesting that love, like a fresh coat of paint, can transform the mundane into something magical. It’s a theme that echoes throughout Waits’ discography, finding parallels in tracks like “I Hope That I Don’t Fall in Love with You” from Closing Time, where the ordinary is tinged with the extraordinary through the lens of love and longing.

Musically, “New Coat of Paint” finds Waits leaning into a jazz-blues fusion that feels like a smoky night in a forgotten bar—a stylistic choice that makes it one of the more upbeat moments on an otherwise introspective album. While tracks like “Martha” from Closing Time are steeped in nostalgia and heartbreak, “New Coat of Paint” offers a more optimistic view, even if it’s tinged with the bittersweet understanding that the fresh start it proposes may be fleeting. The rolling piano lines and subtle bass provide a lively backdrop, while Waits’ gravelly vocals deliver a performance that is equal parts croon and growl, a sound that would become his trademark in the years to come.

“Depot, Depot,” the runner-up from The Heart of Saturday Night, shares a similar thematic preoccupation with movement and transition, capturing the restlessness and yearning for change that marks much of Waits’ early catalog. While “Depot, Depot” takes on the rhythm of a train song, with its steady, relentless pulse and imagery of travel, “New Coat of Paint” remains stationary, focusing on the moment of decision before the journey begins. It’s a song about the possibility of change, the hope of starting over, and the understanding that sometimes, a new look is all it takes to see the world—or oneself—differently.

In the context of this article, “New Coat of Paint” stands out as the top choice from The Heart of Saturday Night for its combination of lyrical wit, musical sophistication, and emotional depth. While “Depot, Depot” is a compelling exploration of transience and the liminal spaces of life, “New Coat of Paint” captures the spirit of renewal with a directness and charm that makes it unforgettable. It’s a song that showcases Waits’ early mastery of language and mood, serving as a bridge between his more straightforward early folk-jazz works and the experimental storytelling style that would define his later albums.

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

Released October 21, 1975

Runner Up: “Warm Beer And Cold Woman”

“Big Joe and Phantom 309” is our pick from Tom Waits’ 1975 live album, Nighthawks at the Diner. Recorded at the Record Plant in Los Angeles over two nights in July 1975, the album was produced by Bones Howe and captures the smoky, late-night ambiance of a small club performance, with Waits delivering his narratives to a live audience. Featuring a band of seasoned musicians—Jim Hughart on bass, Pete Christlieb on saxophone, Mike Melvoin on piano, and Bill Goodwin on drums—the track unfolds like a monologue, blending spoken word with melodic storytelling, a style that would become a hallmark of Waits’ career.

“Big Joe and Phantom 309” tells the eerie tale of a hitchhiker who gets picked up by a truck driver, Big Joe, on a rainy night. As the narrative unfolds, it becomes clear that Big Joe is no ordinary driver—he’s a ghost, a spectral figure who gave his life to save a busload of children ten years earlier. Waits’ delivery is both haunting and empathetic, capturing the loneliness of the open road and the lingering presence of spirits past. The imagery is vivid, as Waits describes the moment the “air brakes come on” and the “lights of an old semi” top the hill. The story is a classic ghost tale set to music, with Waits’ husky voice weaving through the lines like smoke through a dimly lit bar.

While Waits’ debut album, Closing Time, presented songs like “I Hope That I Don’t Fall In Love With You” in a more traditional singer-songwriter style, “Big Joe and Phantom 309” represents a significant departure into more experimental territory. The song’s structure, with its lengthy spoken verses and minimal musical accompaniment, aligns more closely with his later work, such as “Frank’s Wild Years” or “Step Right Up,” where storytelling becomes as integral to the music as melody or rhythm. In this way, “Big Joe and Phantom 309” bridges the gap between Waits’ early, folk-inflected period and the more avant-garde stylings he would explore in the 1980s and beyond.

“Warm Beer and Cold Women,” the runner-up from Nighthawks at the Diner, similarly evokes a world of late-night dives and lost souls. While “Big Joe and Phantom 309” focuses on the mystique of the American highway and its larger-than-life characters, “Warm Beer and Cold Women” delves into the loneliness of urban nightlife, painting a picture of “double knit strangers” and “naugahyde booths.” Both tracks share a sense of melancholy and resignation, but where “Warm Beer and Cold Women” is introspective and rooted in the gritty reality of heartbreak, “Big Joe and Phantom 309” taps into the mythic and the supernatural.

In the context of this article, “Big Joe and Phantom 309” earns its place as the best song from Nighthawks at the Diner due to its unique narrative style and its embodiment of Waits’ transition from folk troubadour to urban raconteur. The song’s chilling, cinematic quality and its blending of reality with ghostly legend make it a memorable entry in Waits’ catalog, setting the stage for the more surreal and experimental works that would define his later career. “Warm Beer and Cold Women,” though a close second, lacks the storytelling depth and atmospheric tension that make “Big Joe and Phantom 309” a standout track in Waits’ early years.

“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, blending poetic lyricism with a raw, emotionally charged performance. Recorded over three days in July 1976 at Wally Heider Studios in Los Angeles, and produced by Bones Howe, Small Change captures Waits at a pivotal moment in his career. The album features a stripped-down production style with only a handful of musicians, including Lew Tabackin on tenor saxophone, Jim Hughart on bass, and Shelly Manne on drums, which gives the songs a sparse, late-night jazz feel that complements Waits’ gravelly, whiskey-soaked vocals.

“Tom Traubert’s Blues” opens with a plaintive piano and Waits’ voice, weathered and weary, immediately drawing listeners into a narrative that is as much about place and atmosphere as it is about pain and longing. The song borrows its chorus from the Australian folk song “Waltzing Matilda,” twisting it into a mournful refrain that serves as both a lament and a refrain for the downtrodden. The lyrics paint a picture of a man who is “wasted and wounded” and struggling through a surreal, nocturnal landscape where “no one speaks English, and everything’s broken.” Waits’ imagery is rich and evocative, detailing encounters with “the Maverick Chinamen” and “the girls down by the strip-tease shows,” creating a vivid portrait of life on society’s fringes.

“Tom Traubert’s Blues” captures the essence of Waits’ ability to blend literary narrative with visceral emotion, a talent that first emerged on tracks like “I Hope That I Don’t Fall in Love with You” from Closing Time and became more pronounced in songs like “Invitation to the Blues” from The Heart of Saturday Night. In “Tom Traubert’s Blues,” Waits takes this narrative style to new depths, employing a stream-of-consciousness approach that makes the listener feel as if they’re living the experience right alongside him. The song is also notable for its stark arrangement, where the piano serves as the primary instrument, underscoring Waits’ voice in a way that amplifies the song’s emotional gravity.

While “Tom Traubert’s Blues” is the undisputed highlight of Small Change, “The Piano Has Been Drinking (Not Me),” the album’s runner-up, provides a sharp contrast with its sardonic humor and biting social commentary. Both songs are quintessential Waits, but while “Tom Traubert’s Blues” is a deeply introspective exploration of personal despair, “The Piano Has Been Drinking” adopts a more whimsical, absurdist approach to the same themes of disillusionment and inebriation. The latter’s surreal imagery—“The piano-tuner’s got a hearing aid, and he showed up with his mother”—adds a layer of dark comedy that balances the album’s heavier moments.

In the context of this article, “Tom Traubert’s Blues” stands out as the best song from Small Change for its profound emotional resonance and its masterful storytelling. While “The Piano Has Been Drinking” offers a clever and entertaining counterpoint, it is “Tom Traubert’s Blues” that captures the full depth of Waits’ artistry at this stage in his career. The song not only cements his reputation as a writer capable of weaving rich, complex narratives but also lays the groundwork for the more experimental and theatrical directions he would explore in subsequent albums like Swordfishtrombones and Rain Dogs. The result is a track that remains one of Waits’ most beloved and critically acclaimed, a defining moment in a career filled with unforgettable songs

“Muriel” – Foreign Affairs (1977)

Released September 13, 1977

Runner Up: “Burma Shave”

“Muriel,” from Tom Waits’ 1977 album Foreign Affairs, stands as a poignant exploration of lost love and the inescapable ghosts of the past. Recorded at Filmways/Heider Recording in Hollywood and produced by Bones Howe, the album continues the nocturnal jazz motifs of its predecessors while deepening Waits’ penchant for lush orchestration and cinematic storytelling. The track features the subtle yet evocative interplay between Jim Hughart on bass, Shelly Manne on drums, and Harry Bluestone leading a string section that adds a haunting layer to Waits’ weathered baritone. “Muriel” is a standout for its introspective lyrics and melancholy atmosphere, capturing the essence of longing with stark honesty.

Lyrically, “Muriel” is a vivid, bittersweet portrait of a man caught in the grip of a past love that he cannot shake. The song opens with the forlorn observation, “Muriel, since you left town, the clubs closed down,” painting a desolate picture of a life interrupted by loss. As the song progresses, it becomes clear that Muriel is more than just a memory; she is an omnipresent specter haunting the narrator’s every move. Waits evokes images of old haunts and “burned out lampposts on Main Street,” using his trademark knack for detailed storytelling to immerse the listener in a landscape where every corner, every dimly lit alley, is a painful reminder of what has been lost.

“Muriel” mirrors the thematic focus of earlier tracks like “Tom Traubert’s Blues” from Small Change, where the protagonist also finds himself wandering through a world of shattered dreams and faded glories. Yet, while “Tom Traubert’s Blues” leans heavily on surreal, almost mythic imagery, “Muriel” stays grounded in the everyday sadness of love gone wrong, much like “I Hope That I Don’t Fall in Love with You” from Closing Time. Both songs reflect Waits’ ability to distill complex emotions into deceptively simple narratives, but “Muriel” adds an orchestral swell that heightens its emotional impact, pulling the listener deeper into the melancholy of the story.

While “Muriel” is the top pick from Foreign Affairs for its emotional depth and narrative clarity, the runner-up, “Burma-Shave,” offers a contrasting but equally compelling tale. “Burma-Shave” takes a different route, using a road-trip setting to delve into themes of escape and the desire to outrun the inevitable. Both songs share a sense of the characters being trapped—by their past, their choices, or their circumstances. But where “Muriel” is a lament rooted in a place that no longer feels like home, “Burma-Shave” is about the desperate pursuit of a new beginning, where every mile marks a futile attempt to leave behind the weight of disappointment.

In this context, “Muriel” stands out as the best song from Foreign Affairs because it encapsulates the album’s overarching theme of longing and introspection with a clarity that is both heartrending and relatable. “Burma-Shave,” while narratively rich and filled with vivid imagery, lacks the intimate, confessional tone that makes “Muriel” so striking. “Muriel” not only showcases Waits’ mastery of the ballad form but also his ability to make the personal universal, turning a story of individual heartbreak into a shared human experience. This blend of personal reflection and universal appeal is what cements “Muriel” as one of the standout tracks in Tom Waits’ early career.

“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 a striking example of the songwriter’s ability to weave vivid narratives through his music, blending the tragic with the tender in a way few artists can. Recorded at Filmways/Heider Recording in Hollywood, Blue Valentine captures Waits at his most raw and confessional, with the album’s production handled by Bones Howe, who had also worked with Waits on his earlier records. The song features Waits on piano, backed by Scott Edwards on bass and Chip White on drums, with the arrangement kept intentionally sparse to allow the lyrics and Waits’ gravelly, world-weary vocals to take center stage.

“Christmas Card From a Hooker in Minneapolis” is written as a letter from a woman named “Charlie,” who paints a deceptively optimistic picture of her life while slowly revealing the harsh realities beneath. The song begins with a series of hopeful anecdotes—she’s pregnant, quit drinking, and is in love with a man who treats her well—but as the verses progress, the cracks in her story begin to show. Her façade crumbles in the final lines: “I don’t have a husband / He don’t play the trombone / I need to borrow money / To pay this lawyer.” This confession hits like a punch to the gut, turning the song on its head and revealing it as a poignant plea for help rather than the redemption story it initially seemed to be.

Lyrically, the song fits well within Waits’ body of work, where characters often find themselves on the margins of society, struggling with their demons in a world that seems indifferent to their plight. In this way, it shares thematic similarities with songs like “Tom Traubert’s Blues” from Small Change, which also features a protagonist trying to make sense of a life that has gone awry. But where “Tom Traubert’s Blues” employs a more surreal, poetic narrative, “Christmas Card From a Hooker in Minneapolis” is striking in its directness and raw emotion. The minimalist arrangement, with Waits’ plaintive piano playing, underscores the desperation and honesty of the narrator, making it one of the most emotionally potent tracks in his discography.

While “Christmas Card From a Hooker in Minneapolis” is the clear standout on Blue Valentine, the runner-up, “Romeo Is Bleeding,” offers a different but equally compelling snapshot of life on the edge. “Romeo Is Bleeding” is more frenetic and cinematic, a noir-inspired tale of a small-time hood who meets a violent end. Both songs showcase Waits’ talent for character-driven storytelling, but while “Romeo Is Bleeding” relies on vivid action and a fast-paced narrative, “Christmas Card From a Hooker in Minneapolis” is more introspective, revealing its truths slowly and painfully over the course of the song.

In the context of this article, “Christmas Card From a Hooker in Minneapolis” stands out as the best song from Blue Valentine due to its stark, unflinching portrayal of life’s hardships, delivered with a blend of pathos and dark humor that only Waits can provide. “Romeo Is Bleeding,” while memorable in its own right, lacks the emotional depth and nuance that make “Christmas Card” such a powerful statement. The latter captures the essence of Waits’ songwriting at this point in his career—a blend of gritty realism and poetic storytelling that leaves a lasting impression long after the last note has faded.

“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 that captures the raw emotion of saying a final goodbye to a lover. Recorded at Filmways/Heider Recording in Hollywood and produced by Waits himself, the album marked a turning point in his career as he began to transition from the jazz-influenced balladeer of his earlier records to the more experimental, genre-defying artist he would become in the 1980s. “Ruby’s Arms” features a lush, orchestral arrangement with strings conducted by Bob Alcivar, and the contributions of Jerry Yester on piano, Larry Taylor on bass, and Chip White on drums, creating a poignant and somber atmosphere that underscores Waits’ mournful delivery.

In “Ruby’s Arms,” Waits sings from the perspective of a man who is quietly leaving his lover while she sleeps, knowing that their time together is over. The song is rich with detailed imagery, from the “railroad boots” and “leather jacket” he takes with him, to the “broken wind chimes” he hurries past as he makes his escape. The lyrics are heartbreakingly direct: “I will steal away out through your blinds / For soon you will be waking,” revealing a deep sense of regret and resignation. The instrumentation, marked by a gentle, melancholic piano line and swelling strings, mirrors the emotional turmoil of the narrator, making “Ruby’s Arms” one of Waits’ most stirring and evocative songs.

“Ruby’s Arms” stands out on Heartattack and Vine not only for its emotional depth but also for its simplicity. Unlike “Christmas Card From a Hooker in Minneapolis” from Blue Valentine, which relies on a conversational narrative structure, “Ruby’s Arms” is straightforward in its melancholy. Its orchestral arrangement hints at the direction Waits would later take with albums like Swordfishtrombones and Rain Dogs, where he explored more complex and eclectic sounds, but here it remains grounded in the tradition of the classic ballad, delivering a direct emotional punch that resonates long after the final notes have faded.

While “Ruby’s Arms” is the standout track on Heartattack and Vine, “Jersey Girl,” the album’s runner-up, offers a different perspective on love and longing. “Jersey Girl,” which would later be famously covered by Bruce Springsteen, is a celebration of romance and the simple pleasures of being in love, a stark contrast to the sorrow and finality of “Ruby’s Arms.” Both songs highlight Waits’ ability to explore the many facets of love, from the painful parting in “Ruby’s Arms” to the joyous optimism of “Jersey Girl.” Yet, while “Jersey Girl” has its charms and has earned its place in Waits’ pantheon of great songs, it lacks the haunting intimacy and emotional weight that make “Ruby’s Arms” so compelling.

In the context of this article, “Ruby’s Arms” emerges as the top pick from Heartattack and Vine for its masterful combination of storytelling, orchestration, and emotional impact. It captures a moment of profound personal loss with a rare authenticity, serving as a fitting conclusion to the album and a bridge to the more avant-garde territory that Waits would explore in the years to come. While “Jersey Girl” remains a beloved fan favorite and a worthy runner-up, it is “Ruby’s Arms” that best exemplifies the depth and range of Waits’ songwriting on this pivotal album.

In The Neighborhood – Swordfishtrombones (1983)

Released September 1, 1983

Runner Up: “Shore Leave”

“In The Neighborhood” is a vivid, almost cinematic portrait of a rough-and-tumble urban landscape, painted with the kind of offbeat, evocative imagery that would come to define much of Waits’ later work. The lyrics are filled with quirky, everyday scenes—a “whinin’ dog,” “goddamn delivery trucks,” and “newspaper sleeping bags”—that combine to create a sense of gritty realism, as well as a touch of the absurd. The song’s chorus, with its repeated invocation of “In the neighborhood,” serves as a kind of refrain for a community on the margins, where life is chaotic, and the lines between tragedy and comedy are blurred. The brass band arrangement, with its off-kilter rhythms and funereal undertones, gives the song a sense of both celebration and lament, capturing the contradictory nature of life in a down-and-out neighborhood.

This track marks a stark departure from Waits’ previous work, like “Ruby’s Arms” from Heartattack and Vine, where the arrangements were more conventional and the songwriting more straightforward. On Swordfishtrombones, Waits began to embrace a new kind of storytelling, drawing on influences from Kurt Weill, Captain Beefheart, and even Harry Partch to create a sound that was distinctly his own. “In The Neighborhood” captures this shift perfectly, with its blend of found sounds, unusual instrumentation, and fragmented, impressionistic lyrics. It’s a song that refuses to conform, embodying the spirit of the entire album, which would go on to influence a generation of artists seeking to push the boundaries of popular music.

While “In The Neighborhood” is the standout track on Swordfishtrombones for its bold innovation and unique approach to storytelling, the runner-up, “Shore Leave,” is another striking example of Waits’ new direction. “Shore Leave” takes the listener on a surreal journey through the disjointed thoughts of a sailor on leave, mixing exotic locations with a sense of dislocation and longing. Both songs highlight Waits’ shift toward a more fragmented, collage-like style of songwriting, where conventional structures are abandoned in favor of a more fluid, stream-of-consciousness approach.

In the context of this article, “In The Neighborhood” stands out as the best song from Swordfishtrombones due to its ability to encapsulate the album’s spirit of innovation and its significance in marking a major turning point in Waits’ career. While “Shore Leave” captures the disorienting effects of a world-weary traveler’s experiences, it is “In The Neighborhood” that best reflects Waits’ newfound artistic freedom and his willingness to explore the darker, more eccentric corners of American life. This song heralds the beginning of a bold new era for Tom Waits, where his music would no longer be confined to traditional boundaries but would instead chart a course all its own, much like the unpredictable streets and alleys of the neighborhood he so vividly describes.

“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 resonant songs, showcasing a new phase in his songwriting and recording style. Rain Dogs, recorded at RCA Studios in New York City and produced by Waits himself, marked a dramatic evolution in his music. The album is known for its eclectic blend of styles, ranging from blues and folk to experimental rock, and features contributions from a diverse group of musicians, including guitarist Marc Ribot, bassist Larry Taylor, and saxophonist Ralph Carney. With Rain Dogs, Waits continued the innovative approach he began on Swordfishtrombones, pushing the boundaries of genre and structure, and “Downtown Train” is a prime example of this transformation.

“Downtown Train” is a yearning, heart-on-sleeve ballad that pairs a driving rhythm with Waits’ raspy, impassioned vocal delivery. The song captures the longing of a man who watches his love from a distance, wondering if he’ll ever be the one to win her heart. “Outside another yellow moon / Punched a hole in the nighttime,” Waits sings, setting a scene of urban loneliness punctuated by the hopeful rhythm of a train running through the city. The imagery is vivid and relatable, as he describes the “Brooklyn girls” trying to break free from their constraints, a motif that recurs throughout Rain Dogs—a celebration of the outsider, the misfit, and the dreamer.

Musically, “Downtown Train” departs from the more abrasive, experimental textures found elsewhere on the album, such as in tracks like “Shore Leave” from Swordfishtrombones or “Time,” the runner-up on Rain Dogs. Instead, it leans into a more conventional rock structure while still retaining Waits’ unique blend of lyrical storytelling and emotional depth. The song’s catchy melody and the driving, percussive beat make it one of the most radio-friendly songs Waits ever recorded, which is perhaps why it later became a hit for Rod Stewart when he covered it in 1989. Yet, despite its accessibility, the song remains unmistakably Waits—a gritty, romantic narrative set against the backdrop of a city that never quite reveals all its secrets.

While “Downtown Train” is the standout track from Rain Dogs, “Time,” the album’s runner-up, offers a different but equally compelling meditation on love and loss. “Time” is a quieter, more reflective piece, its minimalist arrangement and lyrical introspection contrasting with the urgency and movement of “Downtown Train.” Both songs, however, highlight the evolution of Waits’ songwriting on this album—marked by a greater willingness to blend his experimental leanings with more traditional forms. Where “Downtown Train” captures the restless energy of urban life, “Time” offers a somber reflection on its fleeting nature.

In the context of this article, “Downtown Train” emerges as the top pick from Rain Dogs due to its blend of emotional immediacy and musical accessibility. It serves as a bridge between Waits’ earlier, more introspective work and his later, more eclectic experiments, while also standing on its own as a powerful narrative of longing and desire. “Time,” while deeply moving in its own right, lacks the dynamic drive and broader appeal that make “Downtown Train” a standout. As a result, “Downtown Train” not only captures a pivotal moment in Waits’ career but also remains a testament to his ability to craft songs that resonate on both a personal and universal level.

“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 powerful gospel-blues track that exemplifies the bold experimentation and stylistic shift that defined this stage of his career. Franks Wild Years, recorded at Sunset Sound Studios in Hollywood and produced by Waits and his wife Kathleen Brennan, marks a continuation of the idiosyncratic sound Waits first explored on Swordfishtrombones and Rain Dogs. This album further solidifies his move away from the jazz-influenced balladry of his early years and into a more theatrical, genre-blending territory. With musicians like Marc Ribot on guitar, Ralph Carney on saxophone, and Michael Blair on percussion, “Way Down in the Hole” is driven by a deep groove that combines blues, gospel, and a touch of voodoo mysticism, creating a sound that is uniquely Waits.

Lyrically, “Way Down in the Hole” is steeped in religious imagery and metaphor, with Waits’ raspy growl delivering a sermon-like warning about the dangers of temptation and the constant struggle to keep the devil “down in the hole.” The song opens with the line, “When you walk through the garden / You gotta watch your back,” immediately setting a tone of vigilance and spiritual warfare. As the song progresses, it combines a call to faith—”If you walk with Jesus / He’s gonna save your soul”—with a sense of existential dread, underscored by a relentless, percussive beat. The juxtaposition of divine protection with the ever-present threat of evil makes “Way Down in the Hole” a compelling meditation on faith, sin, and redemption, delivered with a raw intensity that perfectly encapsulates the album’s experimental spirit.

Musically, “Way Down in the Hole” stands out for its minimalist yet potent arrangement, marked by a repetitive bass line, spare percussion, and a haunting saxophone that weaves in and out like a snake through the grass. This approach mirrors the stripped-down production style Waits adopted for Franks Wild Years, moving away from the more polished sound of earlier records like Heartattack and Vine in favor of a grittier, more immediate aesthetic. It shares this rawness with other tracks from the album, such as “Hang On St. Christopher,” the runner-up, which opens the album with its own mix of gospel and blues elements, enhanced by distorted horns and a driving rhythm that evokes the feeling of an old, rattling freight train heading straight into the unknown.

While “Hang On St. Christopher” captures the spirit of a reckless, soul-searching journey, “Way Down in the Hole” delves deeper into the inner conflict between sin and salvation, making it the standout track of Franks Wild Years. Both songs reflect the dramatic shift in Waits’ songwriting and recording style during this period, characterized by a willingness to embrace unconventional sounds, themes, and structures. However, “Way Down in the Hole” goes further by combining these elements into a single, unforgettable track that has since become one of Waits’ most iconic pieces, later gaining wider recognition when it was used as the theme song for the critically acclaimed television series The Wire.

In the context of this article, “Way Down in the Hole” is the best song from Franks Wild Years for its unique blend of musical innovation and lyrical depth, capturing the album’s spirit of change and experimentation. While “Hang On St. Christopher” is an essential track that sets the tone for the rest of the record with its urgent, pulsing energy, it is “Way Down in the Hole” that most effectively showcases Waits’ ability to craft songs that are at once deeply rooted in tradition and boldly forward-looking. This song not only represents a significant moment in Waits’ evolution as an artist but also stands as a testament to his enduring ability to challenge and expand the boundaries of contemporary music.

“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, stands as a rebellious anthem against the disillusionments of adulthood, capturing the raw, stripped-down aesthetic that defines this transformative record. Bone Machine, recorded at Prairie Sun Recording Studios in Cotati, California, represents a significant departure from Waits’ earlier work, embracing a rough-hewn, almost skeletal sound that combines elements of rock, blues, and industrial noise. Produced by Waits himself, along with Kathleen Brennan, the album showcases a new level of experimentation, with Waits playing many of the instruments himself, accompanied by musicians such as Les Claypool on bass and David Hidalgo on guitar. “I Don’t Wanna Grow Up” is a standout track, capturing both the childlike yearning and existential dread that permeates much of the album.

Lyrically, “I Don’t Wanna Grow Up” is a defiant declaration against the expectations and responsibilities of adulthood. With its simple yet profound refrain—”I don’t wanna grow up”—the song taps into a universal sentiment of resistance against the inevitable loss of innocence. “When I’m lyin’ in my bed at night / I don’t wanna grow up,” Waits laments, reflecting a world where “nothing ever seems to turn out right.” The lyrics are filled with stark imagery and dark humor, as Waits imagines a future filled with mundane obligations, from “put[ting] a hole in my TV set” to “combing their hair and shining their shoes.” This combination of childlike simplicity and mature cynicism creates a powerful contrast, underscoring the tension between youthful idealism and the harsh realities of adult life.

Musically, “I Don’t Wanna Grow Up” is driven by a minimalist, rhythmic strumming on a detuned guitar and Waits’ gravelly, unpolished vocal delivery, which only adds to the song’s raw, primal energy. The track’s stripped-down instrumentation and lo-fi production are emblematic of the broader sonic landscape of Bone Machine, which eschews the lush, layered arrangements of previous albums like Rain Dogs and Franks Wild Years in favor of a more direct, almost primitive approach. This starkness aligns with the thematic concerns of the album, which grapples with mortality, decay, and the inescapable passage of time. “I Don’t Wanna Grow Up” is both a celebration of youthful defiance and a grim acknowledgement of life’s inevitable march toward adulthood and responsibility.

While “I Don’t Wanna Grow Up” is the clear standout on Bone Machine, capturing the album’s spirit of rawness and rebellion, the runner-up, “Murder in the Red Barn,” offers a more narrative-driven exploration of darkness and mystery. “Murder in the Red Barn” is steeped in gothic imagery and unsettling tension, telling the tale of a crime that casts a long shadow over a rural landscape. Both songs showcase Waits’ ability to craft compelling, evocative stories through his unique blend of lyricism and sound, but while “Murder in the Red Barn” delves into the murky depths of human nature, “I Don’t Wanna Grow Up” retains a certain universality, a plea that resonates with anyone who has ever felt overwhelmed by the expectations of the adult world.

In the context of this article, “I Don’t Wanna Grow Up” stands out as the best song from Bone Machine for its raw emotional impact, its stripped-back production, and its exploration of themes that are both deeply personal and broadly relatable. While “Murder in the Red Barn” adds depth and texture to the album with its dark, brooding narrative, it is “I Don’t Wanna Grow Up” that most effectively captures the essence of Waits’ artistic transformation on Bone Machine. The song’s defiance against the conventions of adulthood reflects Waits’ own refusal to be constrained by the norms of the music industry, making it a defining moment in a career marked by constant reinvention and exploration.

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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, represents a radical departure from the singer’s earlier work, venturing into a realm that blends musical theater, German cabaret, and the macabre. The Black Rider was born out of a collaboration with avant-garde theater director Robert Wilson and legendary writer William S. Burroughs for a stage production of the same name. Recorded primarily at Prairie Sun Recording Studios in Cotati, California, the album showcases Waits at his most theatrical, embracing a darker, more experimental style that would come to define this phase of his career. The production, handled by Waits himself and Kathleen Brennan, his wife and frequent collaborator, involves an eclectic mix of musicians, including Greg Cohen on bass, Joe Gore on guitar, and Ralph Carney on woodwinds, contributing to a sound that is eerie, fragmented, and intentionally unsettling.

The title track, “The Black Rider,” is a haunting, sinister tale that draws listeners into a nightmarish world of Faustian bargains and twisted fates. Inspired by the German folktale Der Freischütz, the song serves as a thematic centerpiece for the album, encapsulating its sense of dread and foreboding. “Come on along with the Black Rider,” Waits croons, his gravelly voice filled with menace, “We’ll have a gay old time.” The lyrics are laced with dark humor and a touch of the grotesque, set against a backdrop of dissonant horns, clattering percussion, and creaking strings that evoke the surreal, carnival-like atmosphere of the stage production. This dissonance and use of unconventional sounds mark a significant shift in Waits’ songwriting and recording style, away from the more structured blues and jazz of albums like Rain Dogs and Swordfishtrombones and toward a more experimental, boundary-pushing approach.

Musically, “The Black Rider” is defined by its use of atypical instruments and sounds—accordion, saw, banjo, and various percussion elements—that give the track a disjointed, dreamlike quality. The arrangement is intentionally sparse and chaotic, reflecting the song’s themes of madness and moral ambiguity. This musical experimentation aligns with the broader sonic palette of The Black Rider as an album, which feels more like a collection of scenes from a surreal play than a traditional studio record. It shares a certain kinship with earlier experimental tracks like “Way Down in the Hole” from Franks Wild Years, but while that song deals with spiritual conflict in a more structured blues-gospel form, “The Black Rider” ventures into much stranger, more theatrical territory.

The runner-up, “T’ Ain’t No Sin,” is another standout track from the album, a cover of a 1929 song by Walter Donaldson and Edgar Leslie that adds a dash of black humor to the proceedings. With its playful yet eerie delivery, the song fits seamlessly into the dark, carnival-esque world of The Black Rider. Both “The Black Rider” and “T’ Ain’t No Sin” highlight Waits’ willingness to embrace the theatrical and absurd, using his music to explore the fringes of human experience and emotion. While “T’ Ain’t No Sin” provides a lighter, more ironic take on the album’s themes, it lacks the thematic weight and sonic innovation that make “The Black Rider” such a compelling centerpiece.

In the context of this article, “The Black Rider” stands out as the best song from the album of the same name because it encapsulates the radical shift in Waits’ artistic vision during this period. The song’s blending of dark humor, avant-garde experimentation, and cabaret-style theatricality marks a bold new direction in his songwriting and production approach. While “T’ Ain’t No Sin” captures the album’s playful side, “The Black Rider” serves as its beating heart, a song that plunges listeners deep into the shadows of its haunted fairground, challenging them to confront the darker corners of the human psyche. This track not only defines the album but also represents a pivotal moment in Waits’ continuing evolution as one of music’s most enigmatic and daring artists.

“What’s He Building?” – Mule Variations

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 and intriguing pieces in Waits’ catalog, epitomizing the radical shift in his songwriting and recording style during this period. Mule Variations, recorded at Prairie Sun Recording Studios in Cotati, California, with production by Waits and Kathleen Brennan, marks Waits’ return to the studio after a six-year hiatus and sees him further pushing the boundaries of his sound into more experimental and narrative-driven territory. With contributions from a host of accomplished musicians, including Larry Taylor on bass, Marc Ribot on guitar, and John Hammond on harmonica, the album navigates between gritty blues, folk, and avant-garde soundscapes. “What’s He Building?” stands out for its spoken-word delivery and use of atmospheric noise, providing a haunting exploration into the unknown.

The track “What’s He Building?” unfolds like a dark monologue, with Waits adopting the voice of a paranoid, nosy neighbor speculating about the mysterious activities of the man next door. The lyrics are filled with suspicion and curiosity, capturing the narrator’s unease with lines like, “What’s he building in there? / What the hell is he building in there?” As the track progresses, the tension escalates, supported by the eerie sounds of creaking doors, muffled bangs, and distorted whispers. There is no melody to speak of—just a cacophony of dissonant sounds that evoke a sense of foreboding and a fear of the unknown. This narrative style reflects a major shift from Waits’ earlier work, such as “Downtown Train” from Rain Dogs, where more traditional song structures were used. Here, Waits discards the conventions of verse and chorus entirely, creating instead an audio theater piece that relies on atmosphere and suggestion.

“What’s He Building?” serves as a testament to Waits’ willingness to experiment, not only in his choice of instrumentation and sound effects but also in his approach to storytelling. The track feels less like a song and more like a piece of performance art, akin to a radio drama from another dimension. It’s a move that recalls the innovative spirit of songs like “The Black Rider” from the eponymous album, where Waits first began to explore theatrical and narrative forms more deeply. However, “What’s He Building?” goes further, blurring the line between music and narrative completely, with Waits employing his raspy, conspiratorial voice to drag listeners into his paranoid worldview, questioning everything and offering nothing in return.

While “What’s He Building?” stands out as the best track on Mule Variations for its sheer inventiveness and narrative boldness, the runner-up, “Get Behind the Mule,” brings a different flavor to the album. “Get Behind the Mule” is a swampy, bluesy dirge that recalls Waits’ earlier work, rooted in the sounds of traditional Americana but filtered through his own unique lens of grit and darkness. Both tracks capture the essence of Mule Variations, with its balance of experimental daring and reverence for musical roots, but while “Get Behind the Mule” grooves with a hypnotic, driving rhythm, it lacks the unsettling psychological complexity that makes “What’s He Building?” so compelling.

In the context of this article, “What’s He Building?” stands out as the top pick from Mule Variations due to its unique approach to songcraft and its embodiment of the significant stylistic changes in Waits’ music at this point in his career. While “Get Behind the Mule” captures the raw, rootsy energy of the album, it is “What’s He Building?” that best demonstrates Waits’ willingness to take risks, challenge his audience, and explore new artistic territories. This song not only captures the spirit of experimentation that runs throughout Mule Variations but also reaffirms Waits’ status as one of contemporary music’s most unpredictable and innovative artists.

“Everything You Can Think”  – Alice (2002)

Released May 4, 2002

Runner Up: “Alice”

“Everything You Can Think,” from Tom Waits’ 2002 album Alice, captures a surreal, dreamlike quality that permeates the entire record, marking a significant change in Waits’ songwriting and recording style. Originally composed for a stage production directed by avant-garde theater artist Robert Wilson in 1992, Alice was finally recorded and released a decade later at In The Pocket Studio in Forestville, California, with Waits and Kathleen Brennan serving as producers. This album is one of Waits’ most lyrically and musically imaginative works, featuring a mix of delicate ballads and discordant, experimental pieces. With Marc Ribot on guitar, Greg Cohen on bass, and Colin Stetson on saxophone, the album moves fluidly between the grotesque and the beautiful, and “Everything You Can Think” is the perfect embodiment of this dichotomy.

“Everything You Can Think” opens with a simple, hypnotic melody that sets the stage for a whimsical yet eerie exploration of the surreal. The lyrics, “Everything you can think of is true / Before the ocean was blue,” immediately invite the listener into a world where logic is upended and imagination reigns supreme. Waits plays with absurd imagery—”Your teeth are buildings with yellow doors / Your eyes are fish on a creamy shore”—blurring the lines between reality and fantasy. The song’s minimalist arrangement, dominated by a repetitive piano line and Waits’ gravelly, whispered delivery, evokes a sense of unease that draws listeners deeper into its strange, dreamlike atmosphere. This marks a departure from the more straightforward narrative style of earlier songs like “I Don’t Wanna Grow Up” from Bone Machine; instead, “Everything You Can Think” leans into abstraction and ambiguity, showcasing Waits’ evolution as a songwriter.

Musically, “Everything You Can Think” employs a delicate balance of sparse instrumentation and atmospheric soundscapes, creating a feeling of otherworldliness that permeates the album. The song’s arrangement is deceptively simple but laden with unexpected touches—like the distant, dissonant strings and the eerie, almost childlike background vocals—that add to its haunting quality. It aligns with the stylistic change evident in Alice, where Waits combines his love for jazz, blues, and folk with more avant-garde elements, exploring themes of memory, obsession, and the subconscious. This song, in particular, captures the album’s essence: a deep dive into the human psyche, where everything—no matter how strange—can be true.

While “Everything You Can Think” stands out as the most compelling track on Alice, the runner-up, “Alice,” offers a more melancholic and melodic counterpoint. The title track, with its lush orchestration and sorrowful melody, serves as a haunting ode to a lost love. Both songs highlight the thematic concerns of the album—memory, longing, and the passage of time—but while “Alice” is a poignant reflection, “Everything You Can Think” takes a more abstract approach, using surrealist imagery to probe the darker, more enigmatic corners of the mind.

In the context of this article, “Everything You Can Think” is the best song from Alice because it represents the album’s spirit of creative exploration and its significant shift in Waits’ artistic direction. While “Alice” captures the emotional core of the record with its haunting beauty, “Everything You Can Think” pushes further into uncharted territory, challenging the listener to abandon conventional logic and embrace the strange and fantastical. It is a testament to Waits’ ability to continually reinvent himself as an artist, moving beyond the familiar to explore new, often unsettling artistic landscapes. This song, much like the album itself, stands as a bold declaration of Waits’ commitment to his craft and his refusal to be constrained by expectations.

“God’s Away on Business” –  Blood Money

Released May 4, 2002

Runner Up: “Everything Goes to Hell”

“God’s Away on Business,” from Tom Waits’ 2002 album Blood Money, is a sardonic and ferocious critique of a world gone awry, epitomizing a seismic shift in Waits’ songwriting and recording style. Blood Money was composed as a companion piece to the Robert Wilson play Woyzeck, based on the German expressionist play by Georg Büchner, and was recorded at In The Pocket Studio in Forestville, California. Produced by Waits and Kathleen Brennan, the album delves deep into darker, more discordant themes and arrangements, abandoning traditional structures in favor of a more theatrical, almost Brechtian approach. Featuring Ralph Carney on woodwinds, Larry Taylor on bass, and Bent Clausen on percussion, “God’s Away on Business” is marked by its angular rhythms, distorted instrumentation, and Waits’ menacing growl, making it one of the most memorable tracks on an album filled with disquieting explorations.

Lyrically, “God’s Away on Business” paints a grim portrait of a world left to its own devices, where justice is a farce and the morally corrupt run the show. “I’d sell your heart to the junk-man, baby, for a buck,” Waits sneers in the opening line, setting the tone for a song filled with cynicism and contempt. As the song progresses, Waits laments a society in decay, where “killers, thieves, and lawyers” are left in charge, and “God’s away on business.” The lyrics weave a narrative of desperation and bleak humor, with Waits playing the role of a street-corner prophet, railing against a world he sees as fundamentally broken. The track is filled with arresting images—a “bloody moon rising” and a “leak in the boiler room”—that serve as metaphors for the impending collapse of moral and social order.

Musically, “God’s Away on Business” reflects the radical shift in Waits’ style that defines Blood Money. The arrangement is sparse but unsettling, with jagged bursts of percussion, honking brass, and Waits’ gravelly voice at its most unhinged. It recalls the dark, cabaret-esque qualities of tracks like “The Black Rider” from the eponymous album, but with a more aggressive, confrontational edge. This song, much like “What’s He Building?” from Mule Variations, abandons traditional melody in favor of a rhythmic, almost spoken-word delivery that heightens its theatricality and tension. The instrumentation—featuring accordion, bowed saw, and other unconventional elements—creates an off-kilter soundscape that perfectly matches the song’s lyrical content, emphasizing the sense of chaos and disorder at its core.

The runner-up, “Everything Goes to Hell,” offers a complementary perspective on the themes explored in “God’s Away on Business.” A cynical, world-weary waltz, “Everything Goes to Hell” captures the same sense of disillusionment and moral ambiguity, with lines like “I don’t believe you go to heaven when you’re good / Everything goes to hell, anyway.” Both tracks reflect Waits’ fascination with the darker side of human nature and his shift towards a more theatrical, narrative-driven songwriting style. However, while “Everything Goes to Hell” has a bitterly ironic tone and a more melodic structure, it lacks the visceral impact and urgency that make “God’s Away on Business” the standout track.

In the context of this article, “God’s Away on Business” stands out as the best song from Blood Money due to its raw intensity, its innovative use of instrumentation, and its unflinching commentary on the human condition. While “Everything Goes to Hell” captures the album’s themes of despair and disillusionment with a subtler, more melodic approach, “God’s Away on Business” offers a more direct and uncompromising take, making it one of the most powerful and provocative pieces in Waits’ catalog. This song, much like the album itself, demonstrates a significant evolution in Waits’ artistry, embracing new forms and darker themes to explore the complexities of the human experience in an increasingly chaotic world.

“Hoist That Rag” – Real Gone (2004)

Released October 3, 2004

Runner Up: “Top Of The Hill”

“Hoist That Rag,” from Tom Waits’ 2004 album Real Gone, represents a profound evolution in Waits’ musical style, diving headfirst into a raw, percussive, and politically charged landscape. Real Gone was recorded at In The Pocket Studio in Forestville, California, and produced by Waits and Kathleen Brennan. This album is notable for its stripped-down, almost skeletal sound—eschewing keyboards entirely and instead focusing on heavy, distorted guitar riffs, deep bass grooves, and frenetic percussion. With Marc Ribot on guitar, Larry Taylor on bass, and Casey Waits on drums and turntables, Real Gone is an album where every track feels like a battlefield, and “Hoist That Rag” is its war cry.

Lyrically, “Hoist That Rag” captures a sense of violent upheaval and relentless conflict, set against a backdrop of gritty, post-apocalyptic imagery. The song opens with Waits invoking characters like Piggy Knowles and Sing Sing Tommy Shay, setting a tone that is both darkly humorous and starkly menacing. “God used me as a hammer, boys / To beat his weary drum today,” he sings, suggesting a world where divine purpose has become entangled with human brutality. As the song progresses, the repeated chorus—“Hoist that rag!”—becomes a rallying cry, calling on listeners to raise the flag, whatever the cost. The imagery is vivid and unsettling: “The sun is up, the world is flat / Damn good address for a rat,” lines that evoke a sense of existential dread and moral ambiguity. The roughness of the lyrics mirrors the rawness of the music, creating a soundscape that is both primal and unnerving.

Musically, “Hoist That Rag” is a departure from the more melodic, orchestrated compositions found on previous albums like Alice or Blood Money. The track is built around Ribot’s searing, flamenco-influenced guitar riff, which cuts through the mix with an intensity that feels almost confrontational. The rhythm section, anchored by Taylor’s deep, throbbing bass line and Casey Waits’ frenetic drumming, drives the song forward with a relentless energy that is both propulsive and chaotic. The production is intentionally lo-fi, capturing a sense of immediacy and grit that enhances the song’s themes of conflict and survival. This is a song that doesn’t just ask to be heard—it demands it, pulling the listener into its tumultuous world of sound and fury.

While “Hoist That Rag” is the standout track on Real Gone, capturing the album’s aggressive, confrontational spirit, the runner-up, “Top of the Hill,” offers a slightly different but equally compelling perspective. “Top of the Hill” opens the album with a burst of beatboxing, distorted vocals, and syncopated rhythms, setting the tone for the experimental, genre-defying journey to come. Both tracks showcase Waits’ willingness to strip his sound down to its raw essentials, using rhythm and texture to create mood and meaning. However, where “Top of the Hill” serves as an introduction to the album’s broader sonic palette, “Hoist That Rag” is its thematic and emotional core—a song that embodies the rage, defiance, and dark humor that runs throughout Real Gone.

In the context of this article, “Hoist That Rag” is the best song from Real Gone for its sheer intensity, its stark, politically charged lyrics, and its innovative use of musical minimalism to convey a sense of urgency and unrest. While “Top of the Hill” captures the album’s experimental ethos and willingness to push boundaries, it is “Hoist That Rag” that most effectively distills the raw power and emotional complexity of Waits’ new direction.

“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, represents a compelling return to form while simultaneously showcasing a refined shift in his songwriting and recording style. Recorded at Prairie Sun Recording Studios in Cotati, California, and produced by Waits and Kathleen Brennan, Bad as Me is Waits’ first album of all-new material in seven years. The album captures a dynamic range of styles, from raw blues and jazz to folk and rock, demonstrating Waits’ unique ability to reinvent himself while staying true to the roots of his distinctive sound. With contributions from long-time collaborators like guitarist Marc Ribot, bassist Larry Taylor, and drummer Casey Waits, “Bad as Me” is both a homage to his past work and a confident step into new territory.

Lyrically, “Bad as Me” is a snarling, swaggering declaration of love and defiance, with Waits adopting the persona of an unapologetic outsider embracing his flaws. “You’re the same kind of bad as me,” he growls, his gravelly voice imbued with a mix of mischief and menace. The song is filled with the kind of playful, street-smart language that has always characterized Waits’ work, reminiscent of earlier tracks like “Hoist That Rag” from Real Gone. Yet, there is also a sense of maturity here—a recognition that the chaos and grit of life are to be embraced, not resisted. The lyrics dance between affection and challenge, drawing the listener into a world where love is rough, uncompromising, and just a bit dangerous.

Musically, “Bad as Me” captures the raw energy that defines the album, combining tight, punchy instrumentation with an infectious rhythm that commands attention. Ribot’s biting guitar riffs and Taylor’s driving bass lines lock in with Casey Waits’ precise drumming, creating a groove that is both relentless and infectious. The production is sharp and focused, stripping away any superfluous elements to allow the song’s core energy to shine through. This approach marks a shift from the more experimental textures found on Real Gone or Alice, favoring a more direct, visceral sound that feels fresh yet deeply rooted in Waits’ blues and rock influences.

While “Bad as Me” stands out as the best song on the album for its immediate impact and confident execution, the runner-up, “Pay Me,” offers a more introspective counterpoint. “Pay Me” is a mournful, accordion-laced ballad that delves into themes of regret and loss, with Waits delivering one of his most tender vocal performances in years. Both tracks showcase the breadth of Bad as Me, capturing its ability to balance raw, gritty energy with moments of quiet reflection. However, while “Pay Me” offers a softer, more contemplative side of Waits, it lacks the fierce, electric vitality that makes “Bad as Me” such a standout.

In the context of this article, “Bad as Me” is the best song from Bad as Me due to its perfect blend of lyrical wit, musical intensity, and stylistic evolution. It encapsulates the spirit of the album—a celebration of life’s rough edges, a dance with the devil, and a nod to both the past and future of Waits’ storied career. While “Pay Me” captures the album’s more introspective moments, it is “Bad as Me” that most effectively embodies the raw, unfiltered sound and the thematic complexity that defines this phase of Waits’ work.

Tom Waits’ Best Song From Each Of His Studio Albums article published on Classic RockHistory.com© 2024