In 1996, Dan Bejar was just a dude from Vancouver with a dollar store guitar and a voice wrecked by nickel shot night at the local dive. His debut as Destroyer from that year, We’ll Build Them A Golden Bridge, is a self-recorded bedroom LP of 16 tracks, avant-garde witticisms delivered by a golden-tongued prophet of 90s lo-fi anti-heroes. Golden Bridge is a silly record, and its title, an allusion to Tolstoy’s War and Peace, is the first hint that Bejar would make a career out of dousing his fairy-tale indie folk in high literary references and layers of intellectual fodder.

But it wasn’t until his next LP, City of Daughters—which turns 20 this week—that Bejar would begin to hone the intimacy, free-association wordplay, and bold instrumentation that would set a roadmap for his career as one of indie rock’s most clever architects and poignant social commentators. These themes would ripple beyond his own 12 albums, and alter the shape of the genre as it moved into the internet age.

“Oh to shy away from days of opulence / Of fake kings and false starts,” Bejar begins despondently on City of Daughters’ first track, “Comments on the World as Will.” It’s a thesis for the work he’s doing here: Although City of Daughters is the first Destroyer album to feature a backing band, a producer, a studio, Bejar sounds lonelier than ever, wailing and whining against rain sounds that are almost too spot on as a metaphor for the way he plays with increasingly slippery and brilliant wordplay.

City of Daughters is a love record, professing love mostly for Bejar’s own relationship with language and connection. It’s about all the different metaphors he can deploy to explore simple topics—love, loss, war, and politics—and the many different, increasingly clever ways Bejar can say the same thing. Mainly: Isn’t love beautiful? Isn’t love awful? Isn’t love grand?

“Think globally / Act nobly / The ties that bind us blind us / I know that’s what they told you / And you know that that’s not true,” he follows on “No Cease Fires!,” a song about ruthlessly pursuing desire. Campfire guitars serve as the lone accompaniment to Bejar’s bare, gruff voice, before bass, drums, and a synthesizer bolster the sound without letting it grow any more overwrought. This is the first appearance of what would become one of Bejar’s most reliable tricks, layering his songs with unlikely combinations of instruments—both acoustic and electric—to amplify the density of his compositions without muddying them up. But it’s his vague circlings around the specific themes of his work, vacillating between the abstractly poetic and on-the-nose elevated realism, that have been the appeal of the Destroyer project for its 22 year existence.

On album highlight “You Were So Cruel,” for example, Bejar recounts a tale of abuse. It’s intentionally vague, more of an etch than a literal account, but his harrowing delivery evokes all the feeling we need to connect with it. He doubles his voice, distorting it in and out of sync with itself: “You were so cruel / And it was her house,” he sings, the second voice fading into the quiet of the home he describes. The song hits not because of its details, but because of the space and distance it grants the listener to inhabit them.

Destroyer is often discussed as a contemporary of acts like Pavement, Silver Jews, and The Microphones—the biggest oddball indie acts of the 90s. Each of these artists helped redefine indie as a sound and ethos, rather than a label association, by harnessing the tension between sloppily performed, loosely arranged instrumentals, and piercing, sardonic lyrics to highlight the density of their thoughts. These artists were unanimously adored in college dorms and amongst the early Pitchfork set because they turned not giving a shit into an artform, a poetry of slack that stood in direct opposition to American idealism in the early 90s. But there was something peculiar about Bejar’s project that always kept him in contrast to these acts.

If bands like Pavement and Silver Jews had the aesthetic of art school dropouts, a little too smart to be unassuming, and a little too disenchanted to ever fully embrace their mission of becoming major acts, then Bejar was the Ph.D candidate focusing on 19th century poetry or something. He’s wholly aware of just how smart he is, yet still expends sizeable energy trying to prove to everybody, but mostly himself, that his brilliance is true, honest, and good.

“I am a tastemaker and I kill things / I am not a tastemaker and I kill things / Albeit acquitted on the first four counts / The compilation released by the nation I founded for you,” he wryly sings on “School, and the Girls Who Go There,” a recollection of collegiate romance. It’s a uniquely human characteristic, to want to show your genius and have people envy and appreciate it. But Bejar never pushes himself all the way there, instead recoiling when he cares too much, drenching himself in a layer of irony or sardonic wit.

City of Daughters is oftentimes too smart for its own good, but when Bejar tones down the vision of himself as poet laureate, his words are beautiful and simple while still retaining the air of fablistic morality that has been his calling card. “I’ve traced your every move then erased them / With a cartographer’s drunken haste / You’ll be new at what you do a long time / Still, victory isn’t mine,” he laments on “Melanie and Jennifer and Melanie.” In that sense, Destroyer’s tales operate more like impressionistic poems than narrative songs—it’s not the specifics that resonate, but rather the common emotion evoked by his bald, often vague, prose and the visceral orchestration that accompanies it.

Destroyer is a warped-pond reflection of Bejar’s rawest emotions; in its density, you can’t help but see yourself in the work, because there’s no one else around. This dichotomy is the potion that Bejar would pour into his life’s work, beginning with City of Daughters. Destroyer is a map that’s been replicated ad nauseum in indie rock, forging a path for songwriting that projects personal shortcomings onto the world to become common practice. The album’s style of folk farce foreshadows the self-conscious stylings of crossover stars like Sufjan Stevens, The Decemberists, and Father John Misty—music that is both winking and shockingly serious, levity paired with searing social commentary and blended into a cocktail that makes the differentiating line indecipherable. It’s Sufjan promising to make 50 albums and getting through two. It’s Father John Misty’s own persona eating him alive.

Bejar never took it to such an extreme, but his constant tinkering between the serious and the fake, truth and lies, laughter and tears, is what City of Daughters, and Destroyer’s outputs to follow, ultimately stand on. That’s why, when he went full yacht rock on 2011’s Kaputt, it didn’t reek of irony or come off as a stunt. After 2006’s Destroyer’s Rubies, perhaps his most successful release to date, it was all but assured that Bejar would begin to tweak his sound yet again.