What’s most remarkable about Tom Waits’s 1973 debut album, Closing Time, is just how unremarkable it is. There are some great songs, sure: the instrumental title track, and Martha, which could be a Neil Diamond tune performed by Willie Nelson, as well as Ol ’55 – covered by Asylum labelmates the Eagles – about whom Waits was publicly sniffy, biting the hand that fed him. The strength of the San Diego troubadour’s songs was never in question, but as an artist lacking identity, he was considered two-a-penny among a myriad of folksy singer/songwriters competing for the public’s affections. By the time he released The Heart of Saturday Night in 1974, he’d forged a clearer direction, as demonstrated by the cloth cap and loose tie worn with dilapidated swagger on the cover – a style contrary to the longhaired, bell-bottomed country rockers fashionable at the time. (Looking For) The Heart of Saturday Night is set from the woozy perspective of the wide-eyed fledgling drinker, a loving ode to Saturday nights on the lash. Over the course of 16 studio albums, Waits would chart the doomed romanticism of the maudlin drunk, as well as documenting his ever-changing relationship with the bottle himself, in varying states of inebriation (The Piano Has Been Drinking is a wonderful example). This track perfectly traces the build-up to the hour of power, identifies the transient moment one has worked all week for and finished off with the “magic of the melancholy tear in your eye”. It’s sentimental and immediately nostalgic for the only day of the week that apparently matters, which implicitly adds to the sense of pathos.

Broadly speaking, Waits’s career is categorised as falling into two stark phases: before Swordfishtrombones and after Swordfishtrombones. Yet, the truth, as ever, is more complex, and the trajectory of his artistic development is a far more nuanced journey than the Road to Damascus epiphany of conventional wisdom. For instance, what a game changer the opener on Small Change must have been when people first heard it in 1976, with the now familiar gadabout narrator emerging fully frazzled and fabulously furry around the edges. Tom Traubert’s Blues is a dauntless display of bravura, a songwriter in complete control, showing off his plumage. Many have commented on the seismic shift undertaken when Waits left Asylum for Island Records later down the line, but the barfly in our midst in 1976 was a world away from the folk-inflected pupa two albums earlier. The thirsty man motif continues unabated here, with a string section to melt even the coldest heart. It has an international flavour, too; bastardising the de facto Australian national anthem in the chorus, it was written in London and recounts an intoxicated crawl around the Danish capital with a girl called Matilda. Tom Traubert’s Blues has attained cult-classic status and may well be his best-loved song. Tom Waits had found his voice, and that voice would be seriously growly from now on.

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3 Step Right Up

Like a scenario from the pages of Bukowski’s Factotum, at the end of the 1960s Tom Waits was living out of his car and working on the door of an LA nightclub called The Heritage. There, he was able to bide his time, reading endless Kerouac and scribbling down the jive-ass phraseology of characters frequenting the nightspot, charged up on endless coffee and cigarettes. “I was sitting there incognito in the inner sanctum of this club – hobnobbing, doing some low-level social climbing,” he said later. Waits had taken the job because he intended to eventually play there himself, which he did, giving himself valuable stage time to hone his craft. His love of the Beats and his meticulous note-taking came together to devastating effect on 1976’s Step Right Up, where he spits a series of skittering slogans and one-liners over a roving jazz bassline, selling an unspecified product with pitches from the sublime (“It mows your lawn and it picks up the kids from school / It gets rid of unwanted facial hair”) to the ridiculous (“Change your life / Change into a nine-year-old Hindu boy, get rid of your wife”). Step Right Up is a hilariously badass proto-rap classic that alludes to the singer’s cynicism towards advertising. This antipathy was obviously lost on the agency working for crisp manufacturer Frito Lay, whose advert used an approximation of the song that was so convincing even Waits thought the person singing it was himself. After a protracted legal battle, the courts ruled his voice was his own property.

4 Christmas Card from a Hooker in Minneapolis

The plinky playfulness and positive chord progression at the outset of Christmas Card from a Hooker in Minneapolis instantly calls to mind the heartwarming energy of Ray Charles’s Georgia on My Mind, though once both songs get underway, the only thing they really share in common are titular US place names 1,000 miles apart. The content of the song is fairly self-explanatory; Waits sings verbatim the imaginary epistle a prostitute writes to the fictional character Charlie about her attempts to make a go of it with a trombonist “who works out at the track” in a new metropolis. She’s clean, sober and pregnant, according to the letter. This hooker with a heart of gold narrative is certainly less patronising than most, a darkly funny scenario that also stirs in us a sense of pity. There’s a twist in the tale, naturally, from one of music’s great raconteurs. The song might have Christmas in the title, but it’s no Christmas song, though full of humour and humanity, it’s the gift that keeps on giving.

5 Heartattack and Vine

His wife Kathleen Brennan once said Waits’s songs fall into two categories, “grim reapers” and “grand weepers”, while the man himself whittled it down to three categories when he released his album Orphans: Brawlers, Bawlers & Bastards in 2006. If we’ve had mostly bawlers so far, then Heartattack and Vine (from the 1980 album of the same name) is probably a brawler, and a bit of a bastard, too. Waits’s bluesy Way Down in the Hole introduced him to a wider audience when it was used as the theme to The Wire in 2002, as Heartattack and Vine had when Levis used Screamin’ Jay Hawkins’ version for a campaign nine years earlier. The singer had no objections to the cop show; he did, however, take umbrage with Levis, forcing the brand to make a grovelling apology in Billboard magazine after he took them through the European courts. Car manufacturers Audi in Spain and Opel in Scandinavia have also found themselves embroiled in costly litigation over the use of his music. “Songs carry emotional information and some transport us back to a poignant time, place or event in our lives,” he said after the aforementioned Frito Lay judgement. “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.” After the Opel judgement, he likened adverts carrying his songs to having an udder sewn to his face. It’s “painful and humiliating”, he said.

Tom Waits – 10 of the best

If Swordfishtrombones is meant to be some kind of artistic year zero, then the love song Johnsburg, Illinois – named after Brennan’s hometown – is a throwback to the tipsy ivory tinkler of yore. Elsewhere, brutal blues bangers such as 16 Shells From a Thirty-Ought-Six stomp harder than ever before, while noirish tales about Bloody Marys and chihuahuas (Frank’s Wild Years) and the cuban funk of the title track, demonstrate Dadaist/Beefheart experimentation and unfettered eclecticism. Johnsburg, Illinois has no intention of reinventing the wheel, however, and what a treat it is, one so tantalisingly short that you want to put it on again and again. “She’s my only true love / She’s all that I think of,” sings Tom sweetly, “look here in my wallet, that’s her.” While the lyric of the song suggests he wanted to show off his new wife to all and sundry, the pair, in reality, have maintained an intensely private relationship away from the media, only adding to their mystique.

7 Rain Dogs

The critical reception accorded to Swordfishtrombones included much profound astonishment, and Waits’s songwriting peers sitting up and taking notice, too. 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.” If Swordfishtrombones had been audacious, then Rain Dogs was more creatively ingenious still, and probably carries more classics per pound than any other Waits record: Cemetery Polka, Hang Down Your Head, Time, Downtown Train, Singapore … every one’s a classic. Best of all, perhaps, is the title track, inspired by Martin Bell’s Streetwise, a documentary about nine homeless youngsters in Seattle to which Waits had contributed music. Commencing with a Gallic accordion flourish, it tangos along with the pinched staccato guitar notes of longtime collaborator Marc Ribot, perhaps best exemplifying that Waitsian sound. If you’re curious to know what Waitsian actually means, then the Collins dictionary defines it as: “hoarse, gravelly vocals, discordant sounds, and the use of unusual instruments”. Rain Dogs is also catchy as hell, in a stealthy kind of a way.

Facebook Twitter Pinterest Hail hail … Tom Waits on stage in 2004. Photograph: MARKUS SCHREIBER/AP

Once in a while, Waits throws up a peculiar, avant garde spoken-word track laced with ambient noises, field-recorded sounds and creepy backing, such as The Ocean Doesn’t Want Me on Bone Machine. Perhaps the most effective of those is What’s He Building? from Mule Variations. “What’s he building in there?” Waits keeps asking, his curtain twitching, his conjecture becoming ever more preposterous as the backing frequencies oscillate, the static becoming yet more deranged. “He never waves as he goes by,” he sneers, “he’s hiding something from the rest of us …” The instruments clatter and the tools continue to clink. “I tell you one thing … he’s not building a playhouse for the children.” The track beautifully captures the suburban paranoia of middle America, and while it was intended to be largely comical on its release in 1999, it has come to seem more sinister as surveillance has become more pervasive post-9/11. “We seem to be compelled to perceive our neighbours through the keyhole,” Waits told the writer Barney Hoskyns. “He has chickens in the backyard and doesn’t get home til 3am, and he says he’s from Florida but the license plate says Indiana … so, you know, I don’t trust him”.

9 Hoist That Rag

Where Bone Machine and Mule Variations explored the American blues, Real Gone was the album where Tom Waits truly embraced hip-hop and beatboxing, with his hacking rhythms apparently recorded in the great man’s own bathroom. Best on that album is Hoist That Rag, described by Alexis Petridis in the Guardian as a “sort of Afrobeat Sea Shanty”, which also featured one of Marc Ribot’s most quietly effective sliding hooks in years. There’s a beautiful simplicity to the song, with the heart only skipping a little faster when Waits delivers the title of the song with a throat-clearing roar. Each repetition of that phrase is a purging act of release. In Hoist That Rag, he seems to attack flat-earthers, and war is never far from his lips, either, while it wouldn’t take too much of a stretch to imagine the rag in question might be the American flag. Suddenly, in 2004, he was becoming more bellicose, more lyrically direct and more overtly political, too.

10 Hell Broke Luce

You suspect that after he quit drinking in the mid-80s, the Tom Waits caricature became ever more grotesque, a kind of inverse and publicly decaying Dorian Gray, while the contented family man got to bring up his children and continue romancing his wife. The repartee, the tall tales and the sophistry are all surely to deflect attention from the person behind this carnival of madness. Cracks began to appear in the façade when Waits was unable to contain his temper over the Iraq war. Where lyrically he had often been deliberately obtuse, the ongoing conflict saw him pen an unofficial triumvirate of protest songs – Day After Tomorrow on Real Gone, Road to Peace on Orphans … and, finally, Hell Broke Luce on Bad As Me. All three were unusually to the point and angry. Hell Broke Luce is the noisiest of the bunch, evoking the feeling of being at war, where you can smell the morning napalm and you want to take cover from the falling bombs and the deafening yell of the NCOs. Aside from the lung-busting menace of Hell Broke Luce, Waits had settled into a familiar groove by 2011’s Bad As Me, though the furrow he’d ploughed to get to that place had been anything but conventional. Working in an industry that until recently was obsessed with youth, Waits is one of those rare artists who is improved the more wizened he becomes, and the more he resembles an old baseball glove.