Release date: October 1985. Label: Island. Running time: 54 minutes. Producer: Tom Waits. Engineer: Robert Musso

When Tom Waits’ tenth album Raindogs was released into the tepid climes of popular music in 1985, it was as if some drooling, horny, horribly deformed circus mutant from Tod Browning’s Freaks had blundered into a power-brokers’ dinner party. Truly this record was the horse with the long neck; a phantasmagorical tour (de force) through a carny of sideshows, blaring almost every conceivable strain of 20th century music; Dixieland jazz, shuckster blues, inbred-idjit rock ’n’ roll, ribald Brechtian balladry and Italian melodrama.

The obsession with found sounds and arcane instrumentation had begun with 1983’s Swordfishtrombones, but here, under the influence of Harry Partch, Agnes Bernelle and his wife Kathleen Brennan, Tom had completed his devolution from gritty Tin Pan Alley piano man into a megaphone-touting dog-and-pony show ringmaster, running riot in a crow-encircled junkyard of sound. The Californian ex-pat’s new musical policy resembled that of some urban bedouin wheeling his trolley through New York City, pillaging skips for knackered ghetto-blasters, wheezing old harmoniums, asthmatic squeezeboxes, planks of wood, trombones, tubas, marimbas and three legged chairs.

Clearly, this orchestra’s conductor had gleefully taken leave of his senses, popping his monocle, brandishing his baton and hopping on one leg like a drunken monkey. "We sail tonight for Singapore", Waits warned on the album’s opening track, "We’re all as mad as hatters here".

But, aside from all this beautiful degenerate noise, Tom could surely turn a phrase. Songs like ‘Cemetery Polka’ exulted in a Fellini-esque familial farce, particularly on routines like, "Uncle Bill will never leave a will/And the tumour is as big as an egg/He has a mistress, she’s Puerto Rican/And I heard she has a wooden leg". And further on in, ‘Gun Street Girl’ co-opted Elmore Leonard’s eye for detail ("He bought a second hand Nova from a Cuban Chinese/And dyed his hair in the bathroom of a Texaco").

Waits had, of course, spun fabulous yarns before, on jazznik outings like Nighthawks At The Diner, but here he was peaking as a wordsmith, effortlessly spewing Chandler-like beat prose on tracks like ‘9th And Hennepin’ ("The steam comes out of the grille like the whole damn town’s ready to blow/ . . . and all the rooms they smell like diesel/And you take on the dreams of the ones who’ve slept there")

Raindogs was recorded in what Waits described as the "oppressive" atmosphere of New York in 1985, when he shared a room in Greenwich Village with actor John Lurie and his brother Evan. Unsurprisingly, it’s an album populated by grotesques, wrecks, leches and malcontents of every rank and kidney. If the artist had already anticipated the burgeoning subterranean bum culture of the rotting Big Apple on ‘Underground’ from Swordfishtrombones, this was the next, hexed generation.

Much of the conceptual action seemed to happen in some dank multi-ethnic quarter of the megapolis, an American Reeperbahn where glum gumshoes guzzle noodles under blue neon moons, suck on gut-rot, blow their last bankrolls in smoky opium dens, and are ministered to by geishas with prosthetic limbs. Raindogs resembled an imaginary anthology of worksongs hymned by 21st century illegal immigrants, all packed "aboard a shipwrecked train", extradited to lands uncharted by cartographers, save for the warning ‘Here Be Monsters’.

But it wasn’t all rum, sodomy and the lash. There were also some of the most utterly gutted man-ballads since Hank croaked his last in the back of a cadillac convertible. At least five of these 19 tunes plumbed the meta-existential despondency of the transient, the contused romanticism of the sot, the crazy despair of what Nietzsche termed "the botched and the bungled".

So, read the whiskeyfied country honk of ‘Blind Love’, the breathtakingly melancholy ‘Downtown Train’ and ‘Time’, and the closing hobo’s lullaby, ‘Anywhere I Lay My Head’, and weep. But most heartrending of all was ‘Hang Down Your Head’, which Tom co-wrote with Kathleen. Revolving around Keith Richards’ ragged telecaster and a rhythm figure too fucked to get out of bed, this has got to be one of the saddest sounds ever emitted by a human in the guise of music. "Hush my love, a train now/But it takes me away from you," Waits laments, and angels reach for the morphine. It doesn’t bleed any harder than this.

For abiding proof of the Raindogs effect, check out the work of Shane MacGowan, Polly Harvey, Nick Cave, Beck, Gomez, and countless other soothsayers in seersucker suits. If you’re talking mavericks, perhaps only Captain Beefheart has ever gone as far out west. Part Dada-ist theatre, part Subterranean Side Story, all heart, the record was so far ahead of its time, we’re all still struggling to catch up with it.

ODD FACT: Rod Stewart had a huge hit with ‘Downtown Train’!

MAGIC MOMENT: Marc Ribot’s dissonant stabs of guitar hectoring Tom’s vocal in the title tune

WHAT HE DID NEXT: Starred with his friends John Lurie and Roberto Benigni in Jim Jarmusch’s Down By Law. Wrote Frank’s Wild Years. In 1987, recorded the live album and film Big Time

CLASSIC LYRIC LINE: "You’re east of east St. Louis/And the wind is making speeches/And the rain sounds like a round of applause" (‘Time’)

STAR TRACK: ‘Hang Down Your Head’

RELATED ALBUMS BY OTHER ARTISTS: Amarcord (Nino Rota), Electric Wolf (Howlin’ Wolf), Let My Children Hear Music (Charles Mingus)