By the time Letting Off the Happiness was released in 1998, then-18-year-old Conor Oberst had already been writing and recording music for five years. A mainstay of the Omaha scene that produced the majority of the early Saddle Creek roster, he had spent time in The Faint, Commander Venus and other short-lived groups throughout the mid-‘90s. In 1995, he began what would become his longest-running, best-known project. Over the next two years, he would begin working under the solo guise of Bright Eyes, writing and recording his literally-titled first album, A Collection of Songs Written and Recorded 1995-1997. Released in January of 1998, it was followed quickly in November by Letting Off the Happiness, the album that truly launched the Bright Eyes brand.

Tapping the tight-knit Omaha music community, Oberst fleshed out the style established on his debut, bringing in a revolving cast of players to create a more fully-realized sound. Recorded in his family’s basement, Letting Off the Happiness was very much of its time, capturing the lo-fi aesthetic so thoroughly permeating the underground in scenes across the country. Tellingly, it features like-minded collaborators from Neutral Milk Hotel—who also had a major year in 1998 with the February release of In the Aeroplane Over the Sea—and of Montreal, still years away from their discofied glam period. Letting Off the Happiness could well be viewed as the epitome of what the indie scene would look and sound like over the next decade, grunge’s detachment having given way to something more emotionally raw, personal and intense in its intimacy.

I give myself three days to feel better/ Or else I swear I’ll drive right off a fucking cliff/ Cause if I can’t learn to make myself feel better/ How can I expect anyone else to give a shit?,” he sings in his fractured warble, the sound of barely contained emotional instability. It’s as good an opening statement as he’d ever manage over the ensuing decades, laying bare the essence of the Bright Eyes aesthetic. He would become more polished and refined over the years, but the raw intensity of Letting Off the Happiness proved most effective and influential, bridging the gap between lo-fi singer-songwriters, emo navel-gazers and literate outsiders. Here he sounds like the new voice of a disaffected generation caught between Gen X slackers and the soon-to-be-christened self-involved millennials.

It’s a role that screams “new Dylan,” but Oberst was something different in his unflinching approach to analyzing himself and those around him, his work coming across as the manic scribblings of a young mind struggling to make sense of the world. “Contrast and Compare” could well have been cribbed from any number of teenage diaries. He sings, “Weeks are slow, days drag on/ Even practice and parties seem long/ But I found myself going/ I guess there’s nothing to do” In the context of an instrumental arrangement that wildly vacillates between sensitive acoustic guitar strumming, pedal steel and almost twee boy/girl vocals and interstitial, heavily distorted guitar chords that eventually give way to a brief explosion of sound, the electric guitars no longer able to be penned in.

Throughout the album, Oberst and company meld acoustic singer-songwriter fare with the sound of underground rock, filtering it through a lens of Americana delivered in a series of rambling narratives. “June on the West Coast” is the album’s most traditional track, sounding every bit like a young Dylan transported to the late-‘90s, Oberst’s reams of lyrics and relatively simplistic chord progression creating a cinematic portrait of a life spent traveling and searching for a greater sense of self and true love. “I thought about my true love, the one I really need/ With eyes that burn so bright, they make me pure” – think of it as his “Sad-Eyed Lady of the Lowlands.”

Oberst continued to evolve, but this album would cast a long shadow, virtually defining his group’s public perception. Fidelity improved over subsequent releases, but the youthful intensity and sincerity rarely reached the same levels of immediacy. To hear the pure essence of Bright Eyes, listeners need look no further than here, with everything you could ever want or need from the band is contained within its 10 tracks. For an album that is now older than its creator at the time of its original release, Letting Off the Happiness carries a world-weariness that feels as relevant now as it did 20 years ago.

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