Tom Waits had one of the wildest trajectories of any rock artist in the 1970s—or possibly ever. A regular presence in San Diego’s coffeehouse folk scene in the late 1960s, he was living out of his car when Herb Cohen, the manager for the Mothers of Invention and Linda Ronstadt, discovered him and helped to secure a record deal with the fledgling Asylum Records. David Geffen and Elliot Roberts had just opened the label in 1971, but already it was a home to some of Southern California’s finest singer-songwriters, including Jackson Browne, Judee Sill, Joni Mitchell, and Neil Young. Waits was plugged as a like-minded artist, based on songs like “Martha” (covered by Tim Buckley) and “Ol’ 55” (covered by labelmates the Eagles).

As the decade progressed, Waits grew weirder and woolier, indulging his penchant for weapons-grade schmaltz as well as his fascination with Beat jazz and the seedier byways of Los Angeles. With each album his voice curdled more deeply into a whiskey growl, often sounding like Louis Armstrong after a bender. His songs sprawled into strange recitations about gutter characters: strippers and barflies, hucksters and grifters, vagrants holding up lampposts and waitresses slinging hash. During it all, Waits maintained strict control over his craft—his music rarely seems haphazard—but bent his songs into new shapes to portray characters and convey emotions that didn’t have much of an outlet in pop music at the time. If his peers and labelmates were Laurel Canyon, Waits was the more sordid Tropicana Motel.

Waits’ current label, Anti-, is reissuing his first seven records, first on CD and on LP over the next few months, chronicling his time at Asylum. Newly remastered but without any bonus material, they form something like a road trip through an America that maybe never existed except in Waits’ own head, or perhaps a novel about an artist defining himself against pretty much every major trend. However, just because they show Waits getting comfortable in his own skin and learning how he could present himself to his fans, these albums comprise more than simply a prelude to his remarkable run of records in the 1980s and 1990s. These seven albums constitute the first act of a remarkable career, even as these reissues complicate that trajectory from assembly-line singer-songwriter to eclectic iconoclast.

Let’s back this Cadillac up a bit. While his teenage friends were playing psychedelic rock and protest pop, a young Tom Waits was discovering his parents’ record collection of big bands and crooners. He got more out of Bing Crosby than he did from the heavy guitar rock coming out of California at the time, but when he started performing, he was a folkie by necessity: He couldn’t afford a band, and coffeehouses were the only venues that would offer him a stage. Many of the songs on his 1973 debut Closing Time were written when Waits was making the rounds in San Diego, like “Ol’ 55,” an ode to the car that carries him away from his girlfriend’s bed on an early morning. It’s the only song with any daylight on this otherwise night-owl collection that’s set in bars and walk-ups and incorporating language he heard eavesdropping while working the door at the Heritage, a folk club on San Diego’s Mission Beach.

These are some of Waits’ most composed songs, the ones that hew closest to popular forms and structures. That’s not a criticism; this is just one melodic, highly structured mode that made these songs coverable by folk singers and shitty country-rock bands. They’re also some of his most focused songs: “I Hope That I Don’t Fall in Love With You” is an ode to missed opportunities, Waits never leaving his stool to tell the story of two strangers who never become anything more. Tender in its depiction of the low and the lonesome, the song is his first glimpse of this barroom milieu, which he would explore much more fully on subsequent albums. It might have sold poorly, but Closing Time reveals an artist who was obviously more than just another SoCal singer-songwriter.

Released in late 1974, The Heart of Saturday Night represents a significant step forward, with Waits inching closer to his signature setting and sound. It’s a concept album about the American Saturday Night and the sense of freedom or obligation or possibility contained in those hours. He’s not interested in the sinner-saint/Saturday night-Sunday morning dichotomies; the morals associated with organized religion have very rarely informed his lyrics. Rather, his characters are motivated by something ineffable, unnameable: “Tell me, is it the crack of the pool balls, neon buzzin’?” he asks of no one in particular on the title track. “Is it the barmaid that’s smilin’ from the corner of her eye? Magic of the melancholy tear in your eye?” Everybody wants a little romance, a little drama, a little signal that all these late nights and early mornings, dive bars and cheap beers, desperate glances and furtive hookups might actually add up to something like a worthwhile life.

Waits captures the melancholy but not exactly the excitement that Bruce Springsteen (his elder by two months) was conjuring in his similarly jazzy, relentlessly loquacious compositions around the same time. But the Boss exuded youth and all the promise contained therein; he was an optimist, a believer in the redemptive powers of rock’n’roll. Waits sounded old before his time, his voice deepening into a growl and his characters sloshing in their resignation. He was 25 going on 70 as he sang “San Diego Serenade,” his most bittersweet break-up ballad.

Elsewhere, he just sounds out of time. The Jazz Age saw a brief resurgence in the 1970s, thanks to movies like The Great Gatsby and novels like E.L. Doctorow’s Ragtime, but those works depict America as a font of wealth, luxury, and frivolity. For Waits, jazz conveyed deprivation and poverty, down-and-outers making the most of a few bucks and getting by on gumption and ingenuity. He convened a small band behind him, some sessions musicians who’d played for Ella Fitzgerald and Count Basie, among others. They lend “Diamonds on My Windshield” and “Fumblin’ With the Blues” a rhythmic elasticity, a Spartan quality that reflects the details of Waits’ world as ably and as convincingly as his lyrics do.

Waits took to the road, extending his persona to the stage and refining it in front of often hostile audiences who didn’t know the Tropicana Motel from the Chateau Marmont. His third album, Nighthawks at the Diner, benefits from those experiences even if it doesn’t really reflect them. It’s a live album, but only sort of. Waits and producer Bones Howe assembled a small audience of friends at the Record Plant in L.A., rolled out a piano and a microphone, and let Waits bend their ears for a few hours. It’s not a real nightclub, more like a Hollywood film set. He introduces it as “Raphael’s Silver Cloud Lounge,” then dives into a superlatively loose set that blurs the lines between song and stage banter. Where does his intro end and “Emotional Weather Report” begin? Is the eleven-minute “Nighthawk Postcards (From Easy Street)” a real song or just a long aside to the audience?

Nighthawks offers the best glimpse of Waits’ world so far, and what’s remarkable is the keen detail, the rich observations, and the sly turns of phrase. A street is full of “used car salesmen dressed up in Purina checkerboard slacks and Foster Grant wraparounds.” Eyeballing a smoky barroom he sees, “Stratocasters slung over the Burgermeister beer guts, and the swizzle-stick legs jackknifed over Naugahyde stools.” Few songwriters make such a meal of proper nouns. Waits has a hundred different ways to describe the moon in the night sky and a thousand different ways to describe a taxicab. One is “piss yellow,” another “bastard amber Velveeta yellow.” To see those words on a page is one thing; to hear Waits deliver them in his Satchmo growl—adjusting his cadence with the timing of a stand-up comedian, deploying the word “Velveeta” like a raunchy punchline—is something else entirely. This live/not live album is a pivotal release for Waits, one that demonstrates the depth of his world and the extent of his dedication to evoking it in fine, eccentric clarity.

To distance himself even further from what he perceived to be the popular image of the rock star, Waits traveled from one show to the next in a jalopy, stayed in fleabags instead of luxury hotels. Rather than coke and heroin, he indulged a vice more in fitting with the world he depicted: booze. Even by his own admission, Waits drank a lot—much more than this persona he was adopting demanded. That friction between him and the industry he had reluctantly joined is the theme, sometimes subtle and occasionally not subtle at all, running through his fourth album, Small Change.

The milieu is familiar, but he makes it all sound fantastical. “The Piano Has Been Drinking (Not Me)” is another song that sounds like it was recorded at 3 a.m. in a bar, but what sets it apart is how Waits presents the setting as nearly surreal: “The piano has been drinking, my necktie is asleep,” he observes from his bench. “The telephone’s out of cigarettes, and the balcony is on the make.” It sounds like the world he has carefully crafted on his first three albums is unraveling at its seams. “Pasties and a G-String” de-eroticizes its low-rent burlesque as a phantasmagoria of despair and boredom. Even “Step Right Up,” with Waits playing the carnival barker on some seedy midway, turns advertising slogans into dark magic.

As wiseacre and rambunctious as that particular song may be, Small Change is electrically charged with a pathos that comes across as both false and real, with Waits playing the raconteur masking his very real sadness behind expressions of sadness. “Bad Liver and a Broken Heart” launches a counteroffensive against his congenital sentimentality, as he slyly undercuts his own pieties: “The moon ain’t romantic, it’s intimidating as hell,” he crows. Deeply embedded in the underbelly, Small Change is nevertheless Waits’ most personal, even is most confessional album, somehow refracting the real person through the persona.

It didn’t take much for Small Change to outsell Waits’ previous albums, and it finally established him as an artist who could headline instead of support. Over the next few years, he would tour elaborate productions that occasionally incorporated fake snow and stage props. He used a cash register as percussion for “Step Right Up” (foreshadowing the pots-and-pans percussion on 1983’s Swordfishtrombones). Now that he had established his particular sound, Waits set about exploring it thoroughly over the next three albums, making slight adjustments and tinkering with various sounds and styles. Strings became more and more prominent, especially on 1977’s Foreign Affairs. Waits’ fifth begins with an instrumental called “Cinny’s Waltz,” which acts as a Technicolor overture for the songs that follow.

The tracks are austere, usually just Waits and a piano. Still, these are some of Waits’ most cinematic compositions, both musically and lyrically. “I Never Talk to Strangers,” a duet with Bette Midler, sounds like a rehash of “I Hope That I Don’t Fall in Love With You,” and “A Sight for Sore Eyes” plumbs the same nostalgia as “Martha,” among other songs. But Waits stretches out on the album’s second side, spinning wild yarns about hitmen and hitchhikers.

Waits always borrowed heavily from Hollywood, not only its grandiose soundtracks but also its neglected glamour and noir tableaux. In 1978, he took his first role in Sylvester Stallone’s Paradise Alley, as a piano player named Mumbles. It wasn’t a stretch; the character was based loosely on him to begin with. Later, “I Never Talk to Strangers” would inspire Francis Ford Coppola to write and direct 1981’s One from the Heart. So it’s fitting that Waits opens Blue Valentine with “Somewhere,” from Leonard Bernstein and Stephen Sondheim’s West Side Story. The song, like the musical, began onstage but was soon translated to the big screen, which parallels the trajectory Waits himself was taking. It must have seemed like an odd cover choice at the time, and Waits gives an odd performance by rounding his vowels and flattening the ends of his words into hisses and moans.

On the other hand, “Somewhere” makes perfect sense thematically: His characters may be hard up, but they’re still dreaming about that promised “place for us.” “Christmas Card from a Hooker in Minneapolis,” a minor hit at the time and a fan favorite for decades after, is one of Waits’ most devastating tunes. He sings in the voice of the title character as she describes a happy life to an old friend: She’s married and off the dope, pregnant and hopeful. Someone might have stolen her record player, but “I think I’m happy for the first time since my accident.” The last verse arrives like a punch in the gut, as she admits she’s making it all up before asking to borrow some dough.

That Minnesota sex worker may be Waits’ richest character, a dreamer who spins an elaborate yarn that even she doesn’t have the heart to maintain. If women have stayed at the margins of his world, usually playing strippers and molls and closing-time hook-ups and more generally serving as fuel for his very masculine sentimentality, here Waits gives a woman a starring role and manages to create a deeply complex and contradictory character. His voice might sound low and gruff, but his performance isn’t mannered or distracting. Rather, he’s deeply sympathetic, especially as he reveals her very modest dream: “I wish I had all the money we used to spend on dope,” he muses. “I’d buy me a used car lot and I wouldn’t sell any of ‘em. I’d just drive a different car everyday dependin’ on how I feel.”

In the context of Waits’ nearly fifty-year career, 1980’s Heartattack and Vine is often discussed as a transitional album, a pivot away from the jazzier settings of his Asylum records and toward a much wilder and weirder mode. And certainly there are clear signposts pointing the directions he would head in the new decade. But in the context of this reissue series, Heartattack and Vine sounds less like a transition and more like a goodbye to those back alleys and underbellies, those barrooms and speakeasies that he once inhabited so easily. On subsequent records that setting would be much less prominent, so it’s fitting that “In Shades” is an instrumental, a smooth, organ-led interlude saturated with nightclub chatter and silverware clatter. Waits himself is missing from the milieu, as though he has fled the scene already. And he ends the album with “Ruby’s Arms,” one of his tenderest compositions. It’s his goodbye to a lover he leaves before the sun comes up, something like a prequel to “Ol’ 55” that brings everything full circle. But it’s also a goodbye to every barfly and every hoodlum and every itinerant on some “inebriational travelogue” he’s met along the way. “I will leave behind all of my clothes I wore when I was with you,” he sings. And then he ends the album with a fond farewell as he rides off into the sunrise: “As I say goodbye… I’ll say goodbye.”

Bon voyage, as well, to the grizzled persona he inhabited throughout the 1970s. No longer a cult figure, he had become what you could reasonably call successful, the music industry bending to him rather than him accommodating its demands. But perhaps the most significant change—the one that really took him out of himself—came in 1978, on the set of Paradise Alley, when Waits met screenwriter Kathleen Brennan. In addition to becoming his songwriting partner, she inspired him to sober up and to expand the sound and scope of his music. “I didn’t just marry a beautiful woman,” he told The Guardian in 2006. ”I married a record collection.” He would never again be quite as prolific as he was in the 1970s—seven albums in seven years—but he would never again be truly alone again in a song.