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Six Definitive Songs: The ultimate beginner’s guide to Tom Waits

Tom Waits is often portrayed as the anti-hero of folk. The singer has traversed genre as easily as he moves from the gutter to the stage and has never truly been held back by anything other than himself. Below, we have pulled together a crash course in what makes Tom Waits great.

The six songs below aren’t necessarily his ‘best’ or most famous but they represent a set of six songs that define Tom Waits as an artist and is sure to leave you wanting more. When Waits arrived on the scene, he did so with a bundle of great songs under his arm and a head full of dreams. Once his debut record Closing Time arrived it did so with little fanfare. Things could have looked rough for Waits—but like every other moment in his career, Waits refused to budge.

Instead, he forged his own path, his own persona and his own goal and quickly became the anti-hero of the American songwriting scene. Often referred to as a Crooner, Waits is what you’d get if you made Frank Sinatra hitchhike between shows in Las Vegas and New York. “I like beautiful melodies telling me terrible things,” Waits once said, and it’s a quote that sums up his creative approach perfectly. “The world is a hellish place, and bad writing is destroying the quality of our suffering,” he added.

His voice is full of the dust on Route 66 and his delivery has been bewildering enough to inspire literal super villains.

Below, we’re looking at Tom Waits’ six career-defining songs.

Tom Waits’ Top 6 Songs:

‘(Looking For) The Heart of Saturday Night’ – The Heart of the Night

When Tom Waits dropped his debut album Closing Time the murmurs around the water cooler weren’t exactly disapproving nor where they heaping praise on Waits. In fact, most people didn’t notice his introduction in the myriad of simial singer-songwriters at the time.

It would take Waits’ second album The Heart of the Night to truly establish himself. One such defining moment would see Waits playfully touch on the varying states of inebriation that lead to a perfect Saturday night on the album’s semi-titular track. It would be the beginning of a career spent dancing in the street.

‘The Piano Has Been Drinking’ – Small Change

The full title of the track ‘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 completed a stint in the famous venue in the early part of June 1976, after which he wrote this song.

It sees Waits taken on the idea of absurdist lyrics and sees such gems as “as the bouncer is a sumo wrestler, cream-puff Casper Milktoast” sung without a hint of irony. Somehow, with Waits’ unusual delivery it not only worked but marked Waits out as a free-think and a likely Hall of Famer.

Another notable moment from the same album is ‘Tom Traubert’s Blues’ but if you’re looking for an iconic moment in this passage of Waits’ career then it can only be his signature tune.

‘Heartattack and Vine’ – Heartattack and Vine

The songs we’ve shown so far are a bit of heartwrenching bunch but this track from Waits’ album of the same name ‘Heartattack and Vine’ proved to be a bit of a bruiser. It saw Waits get down and dirty bringing some whiskey-soaked blues to proceedings.

The track was picked up in 2002 on the iconic TV show The Wire and introduced Waits to a brand new audience. The same can be said when Screamin’ Jay Hawkins’ version of the track being used for a Levi’s advert—but Waits had a huge problem with the company using his track and made them issue an apology for doing so.

Waits has also fought car manufacturers Audi and Opel for using his work saying the sanctity of song is not for sale. “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,” he once said.

‘Johnsburg, Illinois’ – Swordfishtrombones

If you ask any real Waits fan they will likely point to his 1983 album Swordfishtrombones as a more than a crucial moment in his career. The album signified not only a change of style and tempo but also of personal outlook as Waits pursued a quieter life following the completion of the record.

Fitting then that one of the most poignant moments on the album is a tribute to Waits’ wife Kathleen Brennan. An ode to his wife’s hometown also acts as a nostalgia party for the tinkling-ivory days of yesteryear. Waits is at his simplest and sweetest, no absurd lyrics or off-beat structure just a simple song with a strong message.

‘Rain Dogs’ – Rain Dogs

Swordfishtrombones may well have been Waits managing to break himself out of his self-imposed shackles but it was on Rain Dogs that he finally felt free. No longer tied to a degrading image of rock and roll revelry, Waits flourished out from under the microscope.

While ‘Cemetery Polka’, ‘Hang Down Your Head’, ‘Time’, ‘Downtown Train’ and ‘Singapore’ are all classics, it is Waits’ Side Two opener, the titular track, that shines brightest on this record. Inspired by the Martin Bell documentary Streetwise the song becomes a distillation of what makes Waits great.

An unusual and arresting sonic backed by a thick travel toned voice, only matched by the uncanny use of nonsensical instruments. AKA bliss.

‘Hoist That Rag’ – Real Gone

On 2004 effort Real Gone Tom Waits made yet another jump and moved into hip-hop. Well, sort of. More clearly he embraced the beats of hip-hop as the perfect backing for his idiosyncratic tone.

Instead, he took the beat-boxing style and using all variations of instruments, musical surgical or otherwise, created a typically Waitsian sound. ‘Hoost That Rag’ acts as the dystopian anthem for the new millennium and quickly turned Waits into a legend among men.

Never afraid to show his true colours, Waits defies law and sets himself out as the voice of America’s past, present and probably future.

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