A man works his whole adult life and finds himself exhausted, disillusioned. He looks for comfort in his community and feels trapped. He changes his clothes, his hair, his face—it only makes him feel more lost. Marriage isn’t what he thought it’d be, and neither is the money or stability he’d always dreamed about. The things that seemed so important, well, now he’s not so sure. In 1987, a sharp-dressed man stands beside a Cadillac Coupe De Ville on the side of the road. Eight years later, he wanders the deserts of California wearing a large brimmed hat.

Bruce Springsteen’s output between 1987 and 1996—remastered and collected in this new vinyl box set—tells a story of lost faith and self-doubt. If Springsteen were simply the one telling the story and not also the flailing protagonist tangled up in it, there’d be some catharsis, or at the very least a saxophone solo. While the previous box set in this series chronicled his steady rise to fame through 1984’s commercial peak Born in the U.S.A., the tension throughout the music here stems from his abstinence of those things that had endeared him to the public. It’s a darker, messier portrait.

For many fans, this period can be categorized as a time of “Others.” There was the “Other Band”: the cutting if inevitable name given to the group of Los Angeles studio musicians Springsteen assembled after breaking up his beloved E Street Band in 1988. This “Other Band,” who aspired to harden his sound and add a more soulful sensibility, can be heard on three of these seven records: 1992’s dual studio releases Human Touch and Lucky Town and the following year’s sprightly but inessential In Concert/MTV Plugged. With this band, Springsteen played some excellent shows and added a few new classics to his repertoire (“Living Proof,” “If I Should Fall Behind,” “My Beautiful Reward”), but they never quite inspired him like his most trusted collaborators. There’s a reason why they never outgrew their nickname.

Beyond his accompanists, Springsteen spent this era in search of other characters, other places. With his forties on the horizon, he left New Jersey to settle in New York City and later L.A. He recorded his most understated music (on 1995’s solo album The Ghost of Tom Joad) and his most straightforward rock songs (in the murky barroom fog of Human Touch). In the lyrics, he went as deep into character as he’d ever allow himself (in Tom Joad’s thoroughly researched immigrant ballads) and the closest to autobiography he’d ever come. On some of these records, he even sings from the perspective of a wealthy, aging rockstar, one who draws analogies about “eating caviar and dirt” and finds humor in the garish caricatures of himself he finds hanging in North Jersey pawn shops. Sometimes he dresses like a cowboy; sometimes he dresses like a pirate cowboy. If you weren’t specifically looking for him, you might pass him by.

Accordingly, these are often remembered as Springsteen’s other albums. As in, there’s the Bruce we all know and love, and then there’s this stuff. Some of this music is so tangential to his career that it feels almost like parody: 1996’s Blood Brothers EP, now on vinyl for the first time, is a collection of outtakes from the bonus tracks on his Greatest Hits set. Human Touch is an album cobbled together over several languid years during which Springsteen aimed to compose admittedly “generic” music to pad his upcoming live shows. In 1992, a Rolling Stone journalist asked if he considered scrapping that record once he wrote its more inspired companion release, Lucky Town—a fair question for an artist who famously left some of his finest songs on the cutting room floor, who considered shelving even Born to Run because it didn’t measure up to his standards.

“Yeah,” Springsteen responded. “Except that every time I listened to it, I liked it.”

If there’s a revelation to be found during this era, that’s it. There’s a calmness to this music, a breeziness that counters the intensive self-inquiry in the lyrics. “These days I’m feeling alright/Except I can’t tell my courage from my desperation,” he sings in Lucky Town’s “Local Hero,” a distinction that would have hardly been worth mentioning on previous records. For so much of Springsteen's career, desperation and courage came packaged together: That’s precisely what placed so many of his characters on the road, hurtling toward whatever promised land they dreamed up on the other side. Now, everything seemed to have a price. In an era of so much abandonment, the thing that’s really missing on these records is that sense of blinding, reckless optimism, of transcendence somehow within his grasp. In its place is acceptance, hard-won and subdued, the kind of remove that comes when you find something more important in your life than work. The victory is costlier; the wisdom is quieter.

Take, for example, “Straight Time,” a gorgeous, fingerpicked folk song from The Ghost of Tom Joad. Here, Springsteen gives us a quintessential character in his songbook: a factory worker returning to his family after serving an extended prison sentence. On Nebraska, we might have heard the gritty rundown of his crimes. On Born to Run, we’d witness the epic homecoming celebration. In “Straight Time,” Springsteen barely rises above a ghostly, defeated grumble, narrating the unspoken anxiety guiding his character’s every move. “Seems you can’t get any more than half free,” he sighs.

It’s a lesson that Springsteen learned throughout the ’90s. In retrospect, it’s easy to hear this music as a brief detour before he returned to the past he’d been avoiding: moving his bandmate and wife Patti Scialfa and their children back to New Jersey; relaunching the E Street Band; finding new inspiration in their “a-one-two-three-four” rock’n’roll momentum. The band’s reunion, kickstarted in 1999 and more-or-less chuggin’ along to this day, leaves these records in a peculiar place. The remasters are welcome, even if sound quality is rarely the issue on Springsteen LPs. Not to mention, a compilation of this era isn’t quite definitive without his 1990 solo shows, or non-album cuts like the Oscar-winning “Streets of Philadelphia,” or the mini E Street reunion included at the end of 1995’s Greatest Hits. Instead, this collection provides a fascinating if incomplete dive into an uncelebrated era: a map of the places Bruce Springsteen burrowed away while he was presumed to be lost.

The set kicks off with 1987’s Tunnel of Love, his high point as a writer and one of his truly essential releases. Springsteen has said he designed the album to be like a well, something people can return to “for fun, or sustenance, or some faith, or some companionship.” Like Nebraska, it seems designed for solitary listening. Some of Springsteen’s records build and explode; Tunnel of Love sighs and soothes and, even in its darkness, brings a sense of peace.

The ghost of country music glides through Tunnel of Love, as if it came in through the open window in the garage studio where he recorded the album between the hours of 1 and 6 p.m. over the span of three weeks. Exploring a genre that often inspired him thematically more than formally, Springsteen is rumored to have considered making an old-school country record to follow-up the arena rock blockbuster Born in the U.S.A., enlisting virtuoso harmonica and fiddle players in place of his E Street bandmates. Somewhere along the way, he decided to work by himself, mostly on acoustic guitar and a new state-of-the-art synthesizer. The result is a haunted solo collection with a few notable appearances—Nils Lofgren’s slithering, metallic guitar solo in the title track, Patti Scialfa’s affirming vocal accompaniment in “One Step Up.” The mood throughout is isolation, working through the same questions and hoping to summon new wisdom.

In the video for first single “Brilliant Disguise,” Springsteen lets us in on a convincing recreation of that process. Performing alone at the kitchen table, he stares into the camera as it zooms deeper and deeper into his eyes, increasingly focused and intense. “God have mercy on the man who doubts what he’s sure of,” he sings before it fades to black. Those words, and the ensuing fade, form the emotional core of Tunnel of Love: an album that lingers and gleams like the moment ahead of a revelation. “Usually right before I put a record out, I have a lot of conflict,” he said calmly around the time of its release. “This record, it was like… Stuff came very naturally.”

He continued following his intuition. After tossing around the idea of supporting the album with his first-ever solo tour, Springsteen invited the E Street Band along for a brief run of dates with a horn section. Four highlights from those shows, including an acoustic take on “Born to Run” that sounds like some old lullaby unearthed, were released on 1988’s Chimes of Freedom EP. Once the tour wrapped up, Bruce sent the band their pink slips. Around that time, he also divorced his wife of four years, actress Julianne Phillips. In the liner notes of Tunnel of Love—his album obsessed with what happens at the end of our adult relationships—he included a small shout-out to her: “Thanks Juli.”

For a collection of songs about love, there is very little actual intimacy on Tunnel of Love. Its couples are illustrated instead by the spaces between them. “The lights go out and it’s just the three of us,” Springsteen sings in the title track: “You, me, and all that stuff we’re so scared of.” In “Walk Like a Man,” he thinks back to his wedding day but can only seem to remember that troubling look in his father’s eyes when he gazed at him from the altar. The music is lush and warm, but the things that are missing dominate the frame.

Tunnel of Love—and with it, Bruce Springsteen’s imperial run in the ’80s—closes with “Valentine’s Day,” a ballad so slow and serene that it’s almost dirge-like. To a droning waltz, he narrates from the driver’s seat, with “one hand steady on the wheel, one hand trembling over my heart.” A rush of images flashes before him: the dreary, familiar highways of New Jersey; his own mortality; a friend’s new baby; a partner he’s leaving behind, maybe for good this time. In some Springsteen songs, the journey is the point. At any moment on Tunnel of Love, it’s difficult to imagine what lies ahead. How far do you have to travel before you feel free of yourself? What do you expect to find? Where do you even go?