Tom Waits is perhaps the quintessential cult artist, despite recording for large labels alongside successful commercial acts for his entire career. Widely regarded as one of America’s finest songwriters, Waits is known for his harsh and gravely voice, eccentric production methods, and taste for exotic and obscure instrumentation. These attributes certainly make him an acquired taste — one without anything resembling a radio hit in 50 years of music making.
Born in Whittier, Ca., in 1949, Waits began performing a Bob Dylan-heavy repertoire in Hollywood clubs in the early ‘70s and recorded a series of albums as an off-kilter jazz crooner for Asylum Records. In the early ‘80s, Waits married Kathleen Brennan, who would become a co-writer, co-producer, and co-conspirator on much of his greatest work, including an informal trilogy of classic albums for Island Records: 1983’s Swordfishtrombones, 1985’s Rain Dogs, and 1987’s Franks Wild Years.
Waits never became a rock star in the traditional sense, and his albums and tours have become more sporadic since the mid-‘90s. Big names such as Bruce Springsteen, Rod Stewart, and Bob Seger have covered his songs, and respected filmmakers such as Francis Ford Coppola and Jim Jarmusch have asked Waits to score their movies and even act in them. Although no single Waits release has gone platinum, he’s sold more than four million albums over the course of his career and won eight Grammy awards.
This month, Waits began a reissue campaign with remastered vinyl and CD editions of his Island releases from the ‘80s and ‘90s, including Swordfishtrombones, which recently turned 40. It’s as good a time as any to revisit he very best records in Waits’s sprawling discography.
22. One from the Heart with Crystal Gale (1982)
Francis Ford Coppola’s 1982 film One from the Heart was his first serious flop, after The Godfather and Apocalypse Now made him one of the most celebrated filmmakers of the 1970s. It was the first of four Coppola films to feature an appearance by Waits, who made an acting cameo and scored the movie. One For the Heart was far more fortuitous for Waits than Coppola – the score won an Oscar, and on the set Waits became close with his future wife, Kathleen Brennan, who was an assistant story editor. The soundtrack may be the only overproduced album in the Waits catalog, a sentimental set of songs lacking the disarming intimacy of his best piano ballads. Crystal Gayle, the younger sister of Loretta Lynn who became a pop country star in the late ‘70s, sings beautifully on half the tracks, and while there’s a novelty to the oil-and-water contrast of their duets, there’s no real chemistry between them as vocalists.
21. Night on Earth (1992)
Jim Jarmusch is another renowned filmmaker who befriended Waits in the ‘80s and has cast the singer in several features over the years, from 1986’s Down by Law to 2019’s The Dead Don’t Die. In 1991, Waits scored Jarmusch’s Night on Earth, a collection of vignettes about taxi drivers and their passengers that starred Winona Ryder and Rosie Perez. Waits only sings on three tracks on the otherwise instrumental soundtrack, so if you detest his voice but enjoy the creepy pump organ grooves of his mid-period albums, this may be the album for you. Otherwise, it’s whimsical background music, made to waft unobtrusively below film dialogue.
20. The Black Rider (1993)
The final album Waits recorded for Island Records was the first of three collaborations with theater director Robert Wilson. Beat poet icon William S. Burroughs wrote the play, one of his last major works, basing The Black Rider on a German folktale. The album consists of studio recordings of all the music Waits wrote for the project, including three songs with lyrics by Burroughs. The Black Rider is a little grim and monochromatic, with Waits adding a slight German accent to his shouted vocals over woozy arrangements full of tuba and singing saw. As with his film scores, the music can be forgiven for losing something when separated from the visual it was created to accompany. “Cut through all the clatter and you’ll find some terrific ballad writing,” Chris Willman wrote in the Los Angeles Times review.
19. Foreign Affairs (1977)
Bette Midler was well on her way to household name status when she dated Waits and duetted with him on “I Never Talk to Strangers.” With or without the brassy presence of the Divine Miss M classing things up, Foreign Affairs is one of Waits’s smoothest, most romantic albums, which is probably why it’s the least loved of his ‘70s work. “Potter’s Field,” an eight-minute film noir narrative with an inspired horn arrangement, is still reason enough to seek out Foreign Affairs.
18. Big Time (1988)
Waits has only mounted a handful of relatively short tours over the last 40 years, and was never a frequent presence on MTV. His 1988 concert film Big Time is, then, the best or only opportunity for many fans to actually see him sing (it’s currently streaming for free on Tubi, if you’ve never partaken). Big Time had negligible box office receipts and received middling reviews from film critics, but director Chris Blum’s sole feature is a creatively staged film capturing the surreal spectacle of Waits onstage almost as well as Stop Making Sense crystallized the essence of Talking Heads. The album isn’t as entertaining without the Lynch-ian cabaret atmosphere of the visual accompaniment, but it’s still a joy to hear Waits perform highlights from his ‘80s trilogy with musicians from the original albums like Marc Ribot and Ralph Carney.
17. The Heart of Saturday Night (1974)
In 1974, Waits worked with producer Bones Howe for the first time on the Ray Charles-influenced single ”Blue Skies.” While Howe would go on to produce every Waits project for the next seven years, the beautiful and slightly schmaltzy “Blue Skies” was left off of the album which soon followed, suggesting a road not taken. The Heart of Saturday Night’s cover illustration references the Frank Sinatra classic In the Wee Small Hours, which sums up how early Waits was sort of a bizarro Sinatra, offering his own skewed version of Ol’ Blue Eyes at his most introspective and nocturnal.
16. Blood Money (2002)
A decade after The Black Rider, Waits released two more albums simultaneously in 2002 featuring music written for Robert Wilson plays. Blood Money features songs from Woyzeck, which Wilson based on Georg Bucner’s unfinished 1837 tale of jealousy, madness, and murder. You can tell just from looking at the song titles (“Misery Is the River of the World,” “God’s Away on Business,” “Woe,” and so on) that Blood Money is probably the darkest, most hopeless album in the already gritty Waits discography. Most critics compared it unfavorably to its companion album Alice, but there’s a certain appeal in having a go-to album for the pure uncut experience of Waits at his most unforgivingly bleak. “Blood Money is a cacophonous, fearsome and shadowy delight,” Paul McNamee wrote in the NME review.
15. Glitter and Doom Live (2009)
Big Time is the one with a companion film and the songs and sidemen from his most popular albums, but Glitter and Doom Live edges it out as the more essential of Waits’s two conventional concert releases. That’s mainly because it sounds better, capturing the sheer physicality of Waits bellowing out songs like the terrifying opener “Lucinda/Ain’t Goin’ Down” – it’s one thing for Waits to craft unusual vocal sounds in a controlled studio environment, but in concert he doesn’t even sound human at times. By 2008, Waits fans knew that he didn’t tour often and that they were damn lucky to get a ticket, and the palpable excitement of the audience is picked up by the microphones. “The most remarkable part of this recording is how effortless it all feels, its natural juxtapositions smoothly complementing the rough-hewn, crumbly beauty of the music,” wrote Anthony Lombardi in the PopMatters review.
14. Bad As Me (2011)
Waits hasn’t disappeared in the 12 years since this album’s release — he’s acted in several feature films, appeared multiple times on The Late Show with David Letterman, recorded a couple songs for compilations, and played a handful of concerts. It increasingly feels, however, like Bad As Me may be the last collection of new songs we ever hear from him. That would be fine, considering how much he’s already given us, and it would be a pretty good record to go out on. It’s got some rowdy shit-kickers like “Satisfied” and the title track, and it’s as star-studded as any Waits album has been (Flea even plays on a few songs, although he sticks to unassuming walking basslines). “The themes of migration, dissatisfaction and desperation spread out across the album in all kinds of ways,” wrote Andy Gill in The Independent.
13. Alice (2002)
Waits opened his most popular album, Rain Dogs, with an allusion to Lewis Carroll’s Alice in Wonderland: “We sail tonight for Singapore / we’re all as mad as hatters here.” A few years later, Waits scored Robert Wilson’s 1992 play Alice, about Carroll and his muse Alice Liddell, returning to the same sentiment with the morbidly jaunty “We’re All Mad Here.” Though demos of Waits’s Alice score were bootlegged for a decade after a CD was stolen from his car, the songs didn’t see proper release as an album until 2002. The best of the three Waits albums written for Wilson plays, Alice has a wide emotional range, from the haunting title track to the swinging “Table Top Joe.” “His songs have long been preoccupied with society’s outsiders, with murder and desire, and he and Brennan share with Lewis Carroll a linguistic playfulness, a delight in choppy syntax and warped juxtapositions,” wrote Maddy Costa in The Guardian’s review.
12. Heartattack and Vine (1980)
While Swordfishtrombones is widely credited as the Kathleen Brennan-inspired turning point in Waits’ career, he’d already met her while recording Heartattack and Vine, writing “Jersey Girl” about his future wife. As a transitional work, his last proper album with longtime producer Bones Howe features piano ballads like “Saving All My Love for You” which resemble his ‘70s work, and scuzzy guitar-driven songs like the title track which foreshadow the albums to follow. Within a year, Bruce Springsteen recorded “Jersey Girl” as a b-side and even invited Waits to join him onstage at one concert, an early sign that some big names were paying attention to this eccentric troubadour who’d never scored a hit.
11. Bone Machine (1992)
After Waits won his first Grammy for Bone Machine in the fairly new Best Alternative Music Album category, his famous response, according to Jim Jarmusch, was “Alternative to WHAT?” By that point, though, Waits’s long, uncompromising career had earned him many admirers in punk and alt-rock circles. He appeared on Primus’ single “Tommy the Cat” in 1991, and in turn, the band’s bassist Les Claypool played on Bone Machine. Another track on the album, “I Don’t Wanna Grow Up,” would become a rock radio hit for the Ramones a few years later. The craggy lo-fi thump of Bone Machine is anything but a timely pivot to Lollapalooza-friendly grunge, however – as usual, he broadened his fanbase by doubling down on the things only he could do. “It’s Bone Machine’s preoccupation with death that brings these songs to life,” Rob O’Connor wrote in the Rolling Stone review.
10. Real Gone (2004)
Waits going hip-hop is a strange idea on paper. Real Gone, however, features some DJ scratching by his son Casey on a couple tracks and even beatboxing by the elder Waits, incorporating rap influences in unique and organic ways (don’t worry — the song “Make It Rain” is not a Fat Joe cover). As if you could feel him breathe on you, Waits’ vocals are right in your ear for the duration of Real Gone, making it one of his most vivid and visceral Waits/Brennan productions. The 10-minute “Sins of My Father” is the longest song in his entire catalog, a simmering groove that never quits with six verses full of grim biblical imagery. “Waits relishes his vocal tics and impossibly gnarled pipes, shamelessly savoring his homemade racket, building more and more momentum with each new bark,” wrote Amanda Petrusich in the Pitchfork review.
9. Franks Wild Years (1987)
The Swordfishtrombones spoken word interlude “Frank’s Wild Years” introduced the Waits character/alter ego Frank O’Brien in 1983. Waits would revisit and expand on the character over the next few years, playing Frank in a musical play for a three-month theatrical run in Chicago in 1986, and turning those songs into an album in 1987. The late Ralph Carney’s best work as a Waits sideman is all over Franks Wild Years, with distinctively moody horn arrangements on “Hang on St. Cristopher” and the future theme song of HBO’s The Wire, “Way Down in the Hole.”
8. Nighthawks at the Diner (1975)
One of the reasons fans have clamored for tickets to increasingly rare Waits tours for decades is the singer’s gift of gab, and the unpredictable jokes, stories, and tangents in which he often indulges between songs. His two more conventional live albums capture a bit of that famous stage patter, but it’s nearly the star attraction on Nighthawks at the Diner. Waits and producer Bones Howe dressed up a studio at the Record Plant in Los Angeles as a jazz club with a bar, and invited an audience in to watch Waits and his jazzy backing quartet run through a set of new songs, each with its own hilarious introductory monologue. There are some sturdy songs like “Better Off Without a Wife” which would’ve worked as straightforward studio tracks, but the looser material is elevated by the electric energy of the live-in-the-studio experiment. The standout “Eggs and Sausage (In A Cadillac with Susan Michelson)” is the only song Waits has ever performed on Saturday Night Live, during a 1977 episode two years after the album’s release.
7. Orphans: Brawlers, Bawlers & Bastards (2006)
Orphans is a three-disc set with more than 50 songs — some rarities or compilation tracks and some completely new — divided into groups of rockers, ballads, and genre-defying oddities. In its sheer size and variety, the set manages to feel like one of Waits’ greatest achievements, rather than a clearinghouse of minor work. These different moods and modes all jostle up against each other on his proper albums, but whichever kind of Waits you prefer is on offer as an all-you-can-eat buffet on Orphans.
6. Closing Time (1973)
Sometimes it seems like Waits simply sprang forth into the world as a wizened and worldly middle-aged man. His debut album, released when he was just 23 years old, doesn’t really contradict that notion, even if his voice is a little less raspy, his ballads a little sweeter. David Geffen saw Waits perform “Grapefruit Moon” during the young singer’s Monday residency at the Troubadour in West Hollywood, and signed Waits to his burgeoning new label Asylum Records. “Ol’ 55” became the first of many Waits songs to be covered by more commercial artists when Asylum’s marquee act the Eagles included it on 1974’s On the Border. “I Hope That I Don’t Fall In Love With You” is the song that really became a standard, as it has been covered by everyone from 10,000 Maniacs to Jon Bon Jovi and is by far Waits’s top streaming track in 2023.
5. Mule Variations (1999)
Epitaph Records was founded by Bad Religion’s Brett Gurewitz in 1980, and helped drive the ‘90s commercial explosion of West Coast punk with bands like the Offspring and Rancid. That may not sound like a natural home for Waits, but after fulfilling his Island contract, he became the flagship artist of Epitaph’s more musically diverse sister label Anti-, declaring “Epitaph is a label run by and for artists musicians, where it feels much more like a partnership than a plantation.” His first album in six years, Mule Variations was his highest charting release at the time, and arguably one of the best albums ever made by an artist more than 25 years into their recording career. “Picture in a Frame,” “Hold On,” and “House Where Nobody Lives” are deeply moving ballads, but “Eyeball Kid” and the creepy spoken word of “What’s He Building?” affirm that Waits wasn’t going to mellow out or tone down his stranger instincts as he approached 50. In the SPIN review, Sarah Vowell wrote, “He is most believable – and most lovable – telling sad, slow stories; see the gorgeous ‘Georgia Lee,’ an ode to a dead girl in which he asks hoarsely, ‘Why wasn’t God watching? Why wasn’t God listening?’”
4. Small Change (1976)
Small Change was Waits’ most successful album in the 1970s, reaching No. 89 on the Billboard 200 — his highest chart peak for 22 years. Recorded amidst a stretch of hard touring and hard-drinking, it may be Waits’ booziest album, from the drunken Danish escapades of his signature ballad “Tom Traubert’s Blues (Four Sheets to the Wind in Copenhagen)” to the comically slurred “The Piano Has Been Drinking (Not Me).” The single “Step Right Up” crystallized Waits’ fast-talking ‘carnival barker’ mode, a signature of many subsequent tracks. The song was parodied by a Waits soundalike in a 1988 Doritos ad, for which Waits successfully sued the Frito-Lay company for “voice misappropriation and false endorsement” and was awarded more than two million dollars.
3. Swordfishtrombones (1983)
Swordfishtrombones is Waits’ first self-produced album and a departure point where his musical world seemed to rapidly expand. New wife Kathleen Brennan introduced him to more esoteric influences such as Captain Beefheart and Harry Partch, and soon he had a new manager and a new label as well. Swordfishtrombones bursts forth with a dizzying array of instruments never previously heard on a Waits album, including marimba, harmonium, bagpipes, and African and Indonesian percussion, creating a surreal circus of sounds matching the seedy narratives and unpredictable twists of the songs. “Swordfishtrombones was a bombshell to say the least,” wrote Nick Cave and the Bad Seeds’ Jim Sclavunos in a recent piece about Waits’ ‘80s work for the Guardian.
2. Blue Valentine (1978)
It’s to Waits’ credit that he could sing famous songs in his wildly unique voice like a parlor trick, but he’s fairly selective with covers, particularly on his proper albums. The cover of “Somewhere” from West Side Story which opens Blue Valentine is one of those judiciously chosen moments, as he unleashes his growl on a full-on Broadway ballad as an effective contrast to the dusky noir of the rest of the album. The stranger, more vivid Waits of the ‘80s starts to come into view on “Red Shoes by the Drugstore” and “A Sweet Little Bullet From a Pretty Blue Gun,” while “Christmas Card From a Hooker in Minneapolis” is one of his finest comic character sketches. Waits’ then-unknown girlfriend Rickie Lee Jones appears on the back cover of Blue Valentine, a year before the release of her debut album and its improbable pop hit “Chuck E’s in Love.”
1. Rain Dogs (1985)
Keith Richards joined Waits’ growing ensemble of collaborators in 1985. The fact that the Rolling Stones icon is not really the guitarist people discuss when they talk about Rain Dogs, however, is a testament to just how distinctive and inspired Marc Ribot’s performances on the album are. Whether adding piercing exclamation points to the marimba groove of “Clap Hands” or pecking out staccato melodies on “Diamonds and Gold,” Ribot is the rare sideman who can stand out even next to Waits’ voice. Regularly near the top of any list of the best albums of the ‘80s, Rain Dogs was a sleeper hit that took 23 years to go gold (Mule Variations and the Orphans boxed are his only other releases to do so). “Downtown Train” would eventually become the most famous Waits composition thanks to covers by Rod Stewart and Bob Seger, but the fact those rock stars wanted a piece of his talent and cachet was a testament to the unique kind of anti-stardom Waits cultivated in the ‘80s. “By pigging out on a nineteen track LP that goes on for fifty-four minutes without a bad cut, Waits demonstrates how fully he’s outgrown the bleary self-indulgences – booze, bathos, beatnik-ism – that bogged down his ‘70s,” Robert Christgau wrote in Village Voice.