The defining image of Tom Waits’ early career is a photograph taken by Mitchell Rose for Rolling Stone at the Tropicana Motel in West Hollywood in 1977. The singer-songwriter had been renting a room there for a few years by that point, but the photo looks like he’d moved in an hour ago. Beer bottles litter the coffee table in front of him; a guitar case rests atop an oversized cardboard box. Waits leans forward, hands folded, looking skeptical, maybe a little put-out, but certainly not embarrassed by the shabby condition of his domicile. He’s sitting in a folding lawn chair that hasn’t seen a ray of sunshine since the Nixon administration.

The next year, Waits put out his sixth LP on the Asylum label, Blue Valentine. The imprint, started by David Geffen and Elliot Roberts in 1971, was a showcase for the Southern California talent that was defining the post-Woodstock singer-songwriter landscape. Judee Sill’s debut album was its inaugural release, Jackson Browne’s with his first record a few months later, and by the time Joni Mitchell issued For the Roses on Asylum in the fall of 1972, Asylum sat near the center of a scene that was becoming a movement.

Waits knew some of these people from shared bills and the scene revolving around the Los Angeles club the Troubadour, where he’d been discovered by manager Herb Cohen. But he didn’t quite fit in. The prevailing mode of the early singer-songwriters was personal expression—you were supposed to draw from your life for your material, dotting your lyrics with references to friends and lovers and changing the details just enough to maintain plausible deniability. Waits wasn’t interested in this kind of sharing. Instead, he turned the whole idea on its head and based his life on his songs.

Like so many in his cohort, his early encounters with Bob Dylan blew his mind. Where many of his peers came up playing in garage bands, learning how to play Beatles tunes and “Louie Louie,” he fashioned himself as a solo songwriter from the beginning, and Dylan was his North Star. In the 2009 biography Lowside of the Road, writer Barney Hoskyns describes Waits’ earliest performances at a local folk society’s hootenannies as little more than impersonations, where “he was so in thrall to the staple Dylan persona that he wore a harmonica around his neck without ever putting his lips to it.” But where others copped the style and tried to write lyrics that could be considered poetry, Waits channeled the elder artist’s drive for reinvention. By the time he was making a name for himself at San Diego folk hoots, his middle-class suburban upbringing in Whittier, California, suddenly became irrelevant: Music was a good way to become someone else.

Waits got a record deal and, inspired by the Beats and associated countercultural figures like Charles Bukowski, he wrote about down-and-out characters and ragged street life, delivering his songs in the guise of a shabbily dressed nightclub hipster. “The Tropicana became a kind of stage,” Hoskyns observed, “a backdrop to Waits’ twenty-four-hours-a-day performance.” As the ’70s wound down, the songwriter worried that he’d painted himself into a corner. His work had certainly evolved between 1973’s Closing Time and Blue Valentine growing bluesier and rougher as his smoked-scorched voice deepened. But he felt stuck and worried that he was repeating himself.

His search for a new sound was set aside when Francis Ford Coppola tapped him to write and perform songs for One From the Heart. The film’s music would be central to the film’s story and Coppola had fallen in love with the boozy after-hours milieu the songwriter rendered so well, so Waits sat at the piano and got to work, clocking in at the filmmaker’s office like a Tin Pan Alley tunesmith. While composing, he reconnected with Kathleen Brennan, a script supervisor he’d bumped into a couple of times, and they fell for each other hard. Within a week, they were engaged, and from that point forward, his creative output would be split into “Before Kathleen” and “After Kathleen.” Her greatest contribution may have been the way she bolstered his confidence. If Waits feared letting go of the persona that had defined his recording career, Brennan convinced him that something better was within his grasp. She also expanded his musical palette, schooling him on the work of avant-garde artists that would be important in his next phase—Captain Beefheart, Harry Partch, Gavin Bryars.

While continuing work on the soundtrack, Waits knocked out one last album for Asylum with his longtime producer Bones Howe: Heartattack and Vine hit stores in fall 1980. It’s a strong record on which he pushed his voice further and added thick and mean guitar. But it wasn’t a radical departure from what came before. The chrysalis-like transformation would have to wait until the next record: With his contract up and a new family to support, Waits fired Cohen, split with Howe, signed with Island, and released 1983’s Swordfishtrombones.

Producing himself for the first time, Waits raided the musical junk shop and returned with wheezing accordion, fragile glass harmonica, thwacking talking drums, bubbling marimba, and too many miscellaneous percussion instruments to list. His previous work was informed by theater and cinema, but the songs on Swordfishtrombones were uncannily visual, the colors and textures of the sound framing his newly sharp narratives. Characters included a sailor on shore leave, a fugitive on the run from the law, and a homicidal office-furniture salesman who sets fire to the family home. If earlier songs sometimes felt like a slurring drunk telling you a story in a bar; now, they felt vivid and alive. Swordfishtrombones was recorded in California with local players; it would take a move east to New York City just after the record’s release to complete his metamorphosis.

Waits found a creative community almost instantly. In recent years, the city’s experimental downtown music scene had gone overground, and Waits felt a kinship with some of its players. He befriended saxophonist and composer John Lurie, whose band the Lounge Lizards had, in its early days, deconstructed jazz, celebrating the genre while undercutting it with amateurism in a way that fit with Waits’ own playful reverence. Through Lurie, he met jazz guitarist Marc Ribot. Hal Willner, who was the musical director of Saturday Night Live, gave Waits an education on the carnivalesque music of Kurt Weill and invited him to contribute to Lost in the Stars, a tribute to the German composer.

Waits summoned drummer Stephen Hodges and bassist Larry Taylor from California, both of whom had worked on Swordfishtrombones, and Hodges was astonished by how quickly and thoroughly a cabal had formed around the songwriter. “He seemed like the frigging Pope of New York,” he told Hoskyns. “He was taking care of business. He was all over the place.” The degree to which Waits was feeling his oats can be measured by the fact that he asked Keith Richards to play on his record, and the living legend agreed—after years of telling guitarists he was looking for a Stonesy feel, Waits had the self-assurance to ask the man himself.

And he knew how to get what he wanted in the studio. “He really has a good ear, not just for this note or that note, but for understanding how the sound is framing the lyric,” Ribot said in a later interview. “What decade is it, what continent is it on, what kind of room is it in?” Rain Dogs has much in common with Swordfishtrombones—antiquated instruments, metal-on-metal percussion, stomping cabaret numbers alternating with wispy instrumentals. But it has a grungier and more scuffed-up aesthetic that puts guitar, both by Waits himself and Ribot, out front. The latter’s style takes in Cuban syncopation, Southwestern twang, free-jazz skronk, and bluesy rock, but above all it forces you to confront the elemental materials of his instrument, with its electrified hum, heavy wood, and vibrating steel. To hear Ribot play is to understand that a guitar is a machine.

Rain Dogs is more of a band record than its predecessor—it sounds like people playing together in a room, and you notice their interplay at least as much as the arrangements. And everything revolves around the drums. After signing to Island, Waits became one of a few artists in the period—see Peter Gabriel and Robert Fripp of King Crimson—who experimented with a drum setup with few or no cymbals. Even if indirectly, some of this tendency came from the rapidly expanding interest in “world music” in the U.S. and UK in the 1980s, which made work from percussion-heavy traditions more accessible. And some can be traced to earlier strands of experimental rock, specifically the stand-up bashing of Maureen Tucker and the angular rhythms of Captain Beefheart.

For an artist with roots in jazz and rock, deemphasizing cymbals changes the recording’s character. The hi-hat and ride reinforce perception of the rhythm’s grid, allowing the ear to hear the precise meter more clearly, serving as an aural version of dot-and-dash notation on paper. A kit where cymbals are used sparingly can sound heavier, looser, and more rhythmically free—the drums on Rain Dogs roll, tumble, and lurch rather than simply marking time. “Tom always wanted orchestra accuracy with back-alley blues—it had to be loose, and had to be accurate,” said Hodges in a podcast interview. Amplifying the low-end was his use of a 32-inch bass drum better suited for a marching band, the rumble and quake of its diaphragm lending darkness and drama.

In the opening section of Rain Dogs, the ear goes first to the texture of the arrangements and the band’s interactions. “Singapore” is a demented cabaret number that stomps on the 2 and 4, “Clap Hands” has Waits singing with an insectile buzz in the middle of what sounds like a gamelan orchestra, “Jockey Full of Bourbon” is a slinky rumba something like “Ghost Riders in the Sky” as played by Professor Longhair, and both “Cemetery Polka” and “Tango Till They’re Sore” frame their titular movement forms as dances of death.

Throughout the album, guitar and marimba compete for attention. The latter instrument allows percussion to carry rhythm, chords, and melody all at once, while the use of space between mallet strikes means that some pieces unfold with a bare minimum of harmonic information. On “Black Mariah,” Richards plays his instrument like a drum, cozying up to the beat while Waits sings what could be an ancient work song. The title track begins with a sinister accordion that sounds like it’s trying to raise Lon Chaney’s ghost, and Ribot’s guitar rides the marimba as it percolates low in the mix. “Union Square” has a horn section that seems irritated and a percussionist wailing on a brake drum who would probably rather be smashing windows.

For all its sonic pleasures, the lyrics on Rain Dogs might be the best of Waits’ career. New York City is the backdrop for much of the action, but it’s the city as Waits imagines it, a claustrophobic port town filled with transients and desperate characters barely surviving on the margins. “They say if you get far enough away/You’ll be on your way back home,” he sings on the lovely country weeper “Blind Love.” We hear about the weather often, and as you might expect, it ain’t very good. On the gorgeous ballad “Time,” he praises a woman who “said she’d stick around until the bandages came off” and measures the passing hours by watching as “the dish outside the window fills with rain.”

And then there’s one wonderful number that Waits wrote because he could. He survived as long as he did in the business because he wrote songs his peers wanted to sing. That included Closing Time’s “Ol’ 55,” an ode the life on the road that Eagles would record for their 1974 LP On the Border, and “Martha,” on Tim Buckley’s Sefronia, and “Shiver Me Timbers” from The Heart of Saturday Night, which Bette Midler included on a medley on her 1976 record Songs for the New Depression. With “Downtown Train,” he seemed to know exactly what he was doing, creating a copyright that would keep him howling and banging on trash cans into his old age. “I tried to make [it] sound like a pop song,” he told writer Bill Flanagan about the tune, and Hodges noted he tried it first with the core Rain Dogs band but wound up bringing in industry pros, including guitarist G.E. Smith and bassist Tony Levin.

It’s a beautiful piece of work that offers a brief respite from the darkness of the album surrounding it, and it’s the perfect vehicle for a gruff-voiced singer to turn into a hit. Rod Stewart and Bob Seger would record it at almost the same time later in the decade, and Stewart would take his version to No. 3 on the Hot 100 in 1989 and heavy rotation in CVS forevermore.

Revisiting Rain Dogs, one particular verse in Waits’ biggest song leapt out at me: “The downtown trains are full/With all those Brooklyn girls/They try so hard to break out of their little worlds.” One, the idea of “Brooklyn girls” as a category is amusing—it’s not something you often hear in casual conversation, since we’re talking about a borough of two million people whose families come from all over the globe. Perhaps Waits, in love with his new town, was thinking of “Brooklyn girls” of Carole King’s ilk, outsiders who commuted into the city to fulfill their dreams and knew intimately the terrain from their neighborhoods, from rooftop to boardwalk. “Downtown Train” was in that sense Waits’ attempt to channel the wonder of a King co-write with Gerry Goffin, where fantasy is grounded in clear and specific reality.

And then there’s “They try so hard to break out of their little worlds,” a line that could, at first, seem condescending. But if you understand where Waits had been, you know he was feeling every syllable of that line. Since childhood, he’d used music to try to escape his own little world, and after a while, that struggle was eating him up. Until finally, he met someone who believed in him without reservation and finally figured out how to create records like Rain Dogs and make those dreams come true.