Tom Waits is a musician, composer, songwriter, and storyteller that often focuses on the outsiders of society in his work. He almost always delivers lines in a deep, gravelly voice and has transitioned through genres as the years rolled by, shifting from jazz to rock and hip hop to experimental work.
You won’t find him in a list of the most commercially successful singers, but that’s part of his charm. In this article, we’ll go over the 21 best songs Tom Waits ever produced.
1. (Looking For) The Heart of Saturday Night
(Looking For) The Heart Of Saturday Night mirrors the final track of Waits’ album of the same name, seeing him driving around in search of the heart of the night. The “heart” in the song is basically just the essence or source of the energy that accompanies the weekend for younger working people.
The whole track really serves as an illustration of real life, nothing crazy happens, but that’s kind of the point. The more profound point of the song—depending on how you read into it—is that the quest outlined in the track can become both endless and pointless if you aren’t careful about it.
2. Tom Traubert’s Blues (Four Sheets to the Wind in Copenhagen)
This song, which can also go by Tom Traubert’s Blues or Waltzing Matilda, was the opening track for Waits’ fourth studio album, Small Change. It was one of his signature songs and one of the tracks that best showed off his skills as a songwriter. Numerous artists have covered the Australian folk-inspired song over the years, and it’s so mysterious and relatable.
A man finds himself stranded in a foreign land without a dollar to his name, but he isn’t a sympathetic character. He puts himself in the crap situation he’s in and spends all his money on booze. Overall, the track charted well in Europe, popping up to number six on the UK Singles chart and number three in the Netherlands.
3. Christmas Card From a Hooker in Minneapolis
Even if this track wasn’t nearly as good as it actually is, you’d still have to admit that this is one of the best song titles of all time. Christmas Card From A Hooker In Minneapolis is a blunt and funny track that describes a letter written by a prostitute to a man named Charlie. She tells him she is pregnant and married, having gotten clean from drugs and alcohol.
All of it turns out to be a lie though, as she admits she’s sitting in jail but tells him she’ll be out in time for Valentine’s Day. Though it came from his seemingly obscure Blue Valentine album, the song has been covered numerous times and is a major favorite for fans of Waits.
4. Hang on St. Christopher
Hang On St. Christopher is as quintessential Tom Waits as you’re going to find. It just rocks with its superb combination of percussion, horns, and guitar. It also features his vocals that sound like they’ve been put through a megaphone, and there’s no mistaking the intent behind the track.
While it didn’t chart—that I can find—it was named one of The Songs That Shaped Rock by the Rock and Roll Hall of Fame in 2004 and made it onto the UK list of The Best Songs from the 500 Best Albums Ever in 2000.
5. Heartattack and Vine
Heartattack And Vine was the title track of Waits’ 1980 album, taking its name from the famous Hollywood and Vine intersection in Los Angeles. The entire song refers to different transportation methods and directions around the city as well.
It gained most of its fame from being covered by Screamin’ Jay Hawkins for a Levi’s commercial, something Waits did not like. He sued over his music being used and won in a European court, getting an official apology from the brand that appeared in the 1993 issue of Billboard Magazine.
6. Gun Street Girl
Gun Street Girl is the prime example of Waits’ brilliance when he strips down a track and becomes a minimalist. His singsong, chanted lyrics tell the story of a fugitive, a woman, and the wacky events along the way. In the end, it’s a catchy track that delivers a story the way you’d expect from him and keeps you invested in everyone he brings up.
7. Step Right Up
In Step Right Up, Waits’ takes on the persona of a carnival announcer, barking out to potential customers to lure crowds into the attractions. Unfortunately, those guys almost always promise something amazing but those promises are empty and you leave disappointed.
In this song, the narrator is selling a one size fits all product and is generally making fun of the commercials and ads he refuses to allow his music to be used in. That kind of anti-pop star image is one of the things that made him so great in the first place.
Temptation stands out in Waits’ career both for the vocal performance he turned in on this one and the Latin rhythms he used here that were common in his songs but took center stage on this track. Instead of his almost hoarse vocal style, he used a delightful smooth tone that served as both a refreshing change from his typical work and a standard-setting song that showcased his true talents as a vocalist.
9. The Piano Has Been Drinking
Waits’ was always known for including some absurd and hilarious lyrics and there might not be a better song to use as an example of that talent than The Piano Has Been Drinking. As the singer, he imitates a very drunk man, spewing out incoherent phrases and gibberish with an out-of-tune piano playing in the background. It was originally written after he spent an evening playing at Ronnie Scott’s in Soho.
10. Johnsburg, Illinois
Johnsburg, Illinois was a turning point for Waits’ career, the dividing line between what he called “pre-Swordfishtrombones” and “post-Swordfishtrombones.” He shifted from orchestral instruments to writing a song as a tribute to his wife and her hometown, full of nostalgia and the feelings of the glory days of youth.
Easily one of his best tracks and a markedly important song in his great career.
11. Rain Dogs
The whole point of Rain Dogs is to liken lost humans that are in pain to dogs who run away from home but get lost because the rain washes away all the scent markers that would tell them which way to go.
It’s a great metaphor and a sad one, making the song an ode to all the people who sleep in doorways and don’t have a place to call home or feel like they belong. It was inspired by a documentary titled Streetwise, detailing the lives of nine homeless young adults in Seattle.
12. What’s He Building?
Waits wrote What’s He Building? about nosy neighbors that don’t mind their own business. In the song, the listener is meant to be on the side of the guy inside the house, regardless of what he’s building, having contempt for the nosy guy outside.
The track was inspired by Ken Nordine, described by Waits as a great storyteller, and one of those stories was the foundation of “What’s He Building?”
13. Warm Beer and Cold Women
Life can really suck when you get the opposite of what you really want. I mean, if you have a beer and a woman, you’d think you’d be happy, but not if the beer is warm and the woman isn’t into you.
Waits’ took on being an outsider with Warm Beer And Cold Women, which is incidentally the one song on this list that could probably fit in the country genre. I do want to know where the last-ditch attempt saloon is though, it sounds great.
Recommended: Songs about beer
14. Hell Broke Luce
The title of Hell Broke Luce comes from some graffiti found inside Alcatraz during a prison break. Alongside Day After Tomorrow and Road To Peace, this is one of Waits’ protest songs, specifically directed at the Iraq War and one of the times he truly holds nothing back.
A venomous criticism of the government, surrounded by apocalyptic desert scenes that deal with the resulting trauma that comes along with war makes this one of his most potent songs.
15. Jockey Full of Bourbon
Another amazing song from Rain Dogs, Jockey Full Of Bourbon was released as the first single to come from that album. It would go on to be featured in the 1986 film Down By Law and the 1995 film Things To Do In Denver When You’re Dead.
Several artists and bands have released cover versions of the track, with some of the most notable including John P. Hammond, The Blue Hawaiians, and Joe Bonamassa.
16. Goin’ Out West
Goin’ Out West has a spooky feel to it, but that takes nothing away from how funny the song actually is. It’s widely considered a standout track on Waits’ Bone Machine album.
The band just keeps chugging away in this song, and it perfectly juxtaposes a lot of the funny line deliveries to make the track truly something special with a touch of genius.
17. Hoist That Rag
Waits transitioned to and took on the hip hop genre with Hoist That Rag, effortlessly backing up his unique vocal style with beats and beatboxing to create one of his best modern songs. He gets more and more energetic as the track goes on, with each repeated phrase of “Hoist That Rag” going harder and harder and becoming more free-spirited and wild.
It’s also a bit of a turning point for him, as the song is undeniably more directly political than any of his work that came before it.
18. Downtown Train
Downtown Train is a vastly underrated song from Waits’ Rain Dogs album, released in 1985 but not coming out as a single. Jake LaMotta, a famous boxer, was featured in the promo video for the track that was also directed by Jean-Baptiste Mondino.
Later, Rod Stewart would record a cover version of the song that peaked at number three on the Billboard Hot 100 and earned a Grammy Nomination for Best Male Pop Vocal Performance. A later cover by Patty Smyth peaked at 95 on the Hot 100 in 1987 as well.
Recommended: Songs about trains
19. Just the Right Bullets
There was something a bit diabolical going on with Waits on his album The Black Rider. Just The Right Bullets details a peg-legged devil, aptly named Peg-Leg, offering the protagonist some blessed—rather, cursed—bullets that eventually lead to the hero’s downfall.
The lyrics are utter genius, full of half-truths you’d expect from a cursed-object salesman, and delivered just as a salesman would say them. In the end, the promises are empty, and our hero fails in his mission.
20. Anywhere I Lay My Head
A common thing at New Orleans’ funerals is to have a brass band play on the march to the cemetery to lay your loved one to rest. Anywhere I Lay My Head took those elements and builds as it goes on, transitioning from something emotional and raw to beautiful and hopeful.
It would later be covered by Scarlett Johansson on her debut studio album, one that was made almost entirely of Waits’ songs save one original composition.
21. 16 Shells From a Thirty-Ought Six
Some songs work just as well as stories as they do as songs. The track 16 Shells From A Thirty-Ought Six is the tale of a long trip that involves a crow trapped in a guitar, a mule traveling buddy, and an unnamed wilderness that mirrors Waits’ obsession with prison chain gangs.
None of the travelers can get away from each other, and the exchanges begin to get more and more heated throughout the song.
As a contributing writer for Music Grotto, Dakotah writes and produces professional music/media content. He works closely with editorial staff to meet editorial standards and create
quality content for the Music Grotto website. Dakotah is passionate about music in a wide variety of genres, from hip-hop to country and lo-fi to metal, and he enjoys creating music pieces for Music Grotto.