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10 of Tom Waits’ greatest songs of all time

“I like beautiful melodies telling me terrible things”  – Tom Waits

Tom Waits’ gravelly timbre has transported people in a pensive and meditative state, his is a pen so mighty that it engraved words in people’s heart and minds and a spirit that gushed out like an overflowing river breaking the boundaries as well as its banks, gave us exactly what it says in the above quote. Simply put, it sums up Tom Waits’ fierce personality and unrivalled contribution.

The so-called “anti-hero” of folk music, paved his own path and glided through it with inspiring confidence, even when the music scene in America was not ready to appreciate his work. But he did not get stuck in a one-way route. He traversed other lanes and created by-lanes that carried the essence of different musical genres that he was experimenting with.

The spotlight, however, shines on his writing most permanently and it’s a style which was predominantly inspired by the Beat poets. Waits once said, “I’ve always been a word guy, I like weird words and I like American slang and all that and words that are no longer being used… I like to drag them out of the box and wave them around… this is an interesting one, it’s amazing how in addition to punctuation just a little pause in the wrong place can just completely transform the meaning of something.”

A task of choosing only ten songs from a legend’s career leaves one confused. It is a constant cycle of jotting down and scratching out options in a page of the diary and then rewriting them. The ten songs listed here are just a few examples of his milestone creations. We would be delighted if you jump on the bandwagon and tell us your favourites in the comment section below.

10 best songs by Tom Waits:

‘(Looking For) The Heart of Saturday Night’

After the initial vain attempt to make a mark with his debut album Closing Time in 1973, it was Waits’ second album The Heart of the Night in 1974 that established his distinct style and turned some heads. The jazz flavour is enhanced by a neat soundtrack with just an acoustic guitar, upright bass, and one of Waits’ most unaffected vocal performances.

It is a loving ode to Saturday nights, the only day that matters after long and weary hours of work throughout the week. The song, told from the perspective of a drinker, also lays the foundation of Waits’ relationship with his bottle, a theme that he would build up in later songs.

‘Tom Traubert’s Blues (Four Sheets to the Wind in Copenhagen)’

The 1976 album was a game-changer as it offered the audience a fresh take on Waits. Yet again he proved to be a deft songwriter, one who doesn’t let the reins loose and makes sure he is always in control, even during the chaos.

The thirsty man motif continues unabated here. Written in London, it recounts a stroll around the Danish capital with a girl called Matilda. The incorporation of the Australian folk song ‘Waltzing Matilda’ in the chorus part takes the song to another level. With a magnificent string section, the song is definitely one of Waits’ finest.

‘The Piano has been Drinking’

Waits’ signature absurdist lyrics are on full display in this song. Waits imitates a drunkard who is spouting nonsense phrases recalling a “somewhat abused, slightly-out-of-tune piano that one would expect to find in the corner of a bar left out in the rain.”

The songs full title ‘The Piano Has Been Drinking (Not Me) (An evening with Pete King)’ refers to the director of London’s famous jazz club Ronnie Scott’s in Soho. Waits wrote the song after completing a stint in this venue and all of the smoky-jazz tones that emanate from it can be traced back to the legendary club.

‘Christmas Card from a Hooker in Minneapolis’

This 1976 song has a strong jazz seasoning that lingers even after the song ends. The bittersweet melody of the song immediately reminds one of Ray Charles song ‘Georgia on My Mind.’

The self-explanatory lyrics narrate a letter written by a prostitute to a man named Charlie. She lies through and through telling him how happy she is until the writer persona interferes and tells Charlie that all of it is untrue and that she is will be eligible for parole in Valentine’s Day.

The lyrics which have been described as “laconic first-person sketch” are sure to tear one up yet leaving a faint smile at the corner of the lips. It’s the perfect combination of what makes Waits’ such an enticing figure in music.

‘Heartattack and Vine’

Compared to the bunch of heart-wrenching songs given above, the title track of the 1980 album of the same name is a bit of a bruiser. It witnesses Waits’ new area of interest, whiskey-soaked jams and sees the singer revel and excel in the blues just as Picasso had done before him.

The track gained a new fanbase with its use in various advertisement and TV shows. For example, in 2002 on the iconic TV show The Wire and introduced Waits to a brand new audience. However, Waits had an issue with companies using his song and filed a lawsuit.

He once said, “It’s no wonder a corporation would want to hitch a ride on the spell these songs cast and encourage you to buy soft drinks, underwear or automobiles while you’re in the trance…” One of Waits’ finest numbers should never be attached to such advertisements they should be played loudly and without a care in the world.

‘Johnsburg, Illinois’

Waits’ career can be divided into two halves: pre-Swordfishtrombones and post-Swordfishtrombones. The 1983 album was a crucial moment for his career. The music moved away from the piano and string orchestra arrangement of the 1970s and the tempo pattern also changed.

The track is a tribute to Waits’ wife Kathleen Brennan. The song is about his wife’s hometown and indulges in a nostalgic and heartwarming recollection of the golden days of yore. Though the lines “She’s my only true love / She’s all that I think of….look here in my wallet, that’s her” may seem like Tom publicly declaring his love for Brennan, in reality, he was a very private person who maintained a strict line between personal and public life.

There’s no doubt that this track reigns as one of Waits’ finest.

‘Rain Dogs’

Elvis Costello told Patrick Humphries in his book The Many Lives of Tom Waits, “I think I was envious of his ability to rewrite himself out of the corner he’d appeared to have backed himself into.”  This what exactly happened in Rain Dogs, the 1985 album. Waits shined brighter than in Swordfishtrombones.

While ‘Cemetery Polka’, ‘Hang Down Your Head’, ‘Time’, ‘Downtown Train’ and ‘Singapore’ are all classics, it is the Side Two opener and the titular track that stands out as one of his best.

The song was inspired by Martin Bell’s Streetwise, a documentary about nine homeless youngsters in Seattle. It curated the term Waitsian sound which is described as “hoarse, gravelly vocals, discordant sounds, and the use of unusual instruments” in the Collins dictionary.


The 1987 album has Latin tinges that were deeply ingrained in Waits’ music since he grew up in California taking frequent trips to Mexico. The song’s slowly percolating rhythms and broken-jukebox horns all add to one of the best vocal performances Waits has ever turned in.

What makes the album special is the way he uses his voice. He moves away from the raw and hoarse vocal style to a more controlled and smooth one. He uses falsetto, which he refers to as his “Prince voice” and its simply delightful as the perfect refrain from Waits’ otherwise non-royal tones.

‘Hoist That Rag’

On 2004 Waits made yet another smooth transition adapting the hip hop style. He mainly used the beats of hip hop along with beatboxing to back up his unique vocals and turn this into one of the singer’s more modern classics.

The track acts as a dystopian anthem and reflects the bold spirit that Waits embodies. With each repetition of the phrase, it becomes more and more free-spirited. The lyrics see a more direct and political approach compared to his previous songs.

‘Hell Broke Luce’

Taking its title from a piece of graffiti carved into the walls of Alcatraz during a prison break, ‘Hell Broke Luce’ from the 2011 album, witnesses Waits agitating on behalf of the beleaguered Army grunt. ‘Day After Tomorrow on Real Gone’, ‘Road to Peace on Orphans’ and ‘Hell Broke Luce’ are a bunch of protest songs written by Waits on the Iraq War and he doesn’t hold back.

The song evokes the traumatising feeling of being at war and is the angriest and noisiest among the three. It is an apocalyptic field chant that conjures visions of a dusty, demoralized desert.

Waits criticises the government and hurl the lines: “How is the only ones responsible for making this mess / Got their sorry asses stapled to a goddamn desk?” at them. It’s one of the singer’s most potent affairs.

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