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Tom Waits has always been bound to the city of New York. Even in his early days loafing around the nightclubs of Los Angeles, his evolving stage persona belied a fascination with the city’s rich literary heritage – specifically the beat poets and writers who had managed to transfigure this still-young city from an industrial rat-trap into an urban anti-Eden, every apartment and dingy nightclub of which held the possibility of enlightenment or, if not that, a night on the hard liquor.

The city’s musical history also called out to Waits. From his small apartment in Silver Lake, L.A, he cast his rod over the wide bulk of the North American continent, reeling in the folk sound of Greenwich Village greats such as Bob Dylan and Dave Van Rank. At the same time, he found himself increasingly drawn in by the modal jazz sound that had evolved in New York’s subterranean venues, where the likes of Duke Ellington, Miles Davis, John Coltrane, Chet Baker, and Bill Evans had spent years honing their cryptic, tobacco-laced style.

Throughout the 1970s, Waits and New York continued their long-distance romance, with the singer stopping by at regular intervals for tour dates and residencies at the likes of the Reno Sweeney nightclub. It wasn’t until 1984, shortly after the release of Swordfishtrombones, that Waits finally decided to replace the oranges and sunshine of California for the urban sprawl of New York. When asked about why he’d decided to leave the west coast, Waits joked that he’d moved “for the peace and quiet, you know”.

In reality, New York offered little in the way of peace and quiet. What it did offer was an infinite inspiration. For Wait, walking around New York was like running along a never-ending conveyer belt of kaleidoscopic images, all thrown together in a swirl of noise and life and colour. “New York Forces you to be in endless surreal situations,” Waits said in 1988. “Where the gun-metal Mercedes pulls up into the puddle of blood, and out steps the 25- karat, blonde transvestite with the two-dollar wristwatch. It’s always setting you off balance”.

This land of juxtapositions proved to be an incredibly fruitful plain for which Waits to graze on – inspiring him to write some of his most innovative and unusual work. Here, we’ve sorted through this discography to bring you a journey through New York-based on the lyrics of Tom Waits. You can use it as a roadmap if you want, or you can visit the sites at random. So, where to begin…

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