How a Portland songwriter’s existential album bridged the gap between lo-fi and pop stardom

Ideas & Philosophy · Published 3 October 2026 Swipe more like this →

In short: Elliott Smith’s third album, Either/Or, remains his best-selling release despite never charting. Named after a Kierkegaard philosophical text, the 1997 record captured a pivotal transition in Smith’s sound, eventually propelling him toward an Academy Award nomination and a major label deal after catching the ear of director Gus Van Sant.

Recorded between 1995 and 1996 across various Portland locations—including Smith’s own home and the Heatmiser House—Either/Or serves as a stylistic bridge. Critics often describe it as the midpoint between the stark, lo-fi intimacy of Smith’s earlier work and the polished studio sheen of his later records, XO and Figure 8. While the album features the songwriter’s signature acoustic-guitar confessionals, it also introduces a newfound brightness and pop sensibility that marked a thematic shift in his career.

The album’s title is a direct nod to Søren Kierkegaard’s philosophical treatise on the tension between subjective aesthetic experience and objective ethical being. This intellectual framing reflects Smith’s academic background at Hampshire College. Though the title track was recorded during the sessions, it was omitted from the final release, only appearing years later on the posthumous compilation New Moon. The lyrics themselves are deeply rooted in Smith’s surroundings, frequently referencing specific Portland landmarks like the Alameda neighborhood and the local Rose Festival.

Though the album failed to chart upon its February 1997 release on the Kill Rock Stars label, its cultural footprint grew significantly. Director Gus Van Sant incorporated three tracks—"Between the Bars," "Angeles," and "Say Yes"—into the Good Will Hunting soundtrack. This exposure, combined with Smith’s performance of the standalone single "Miss Misery" at the 1998 Academy Awards, pushed him into the international spotlight. By March 2017, the album had sold 429,000 copies in the United States.

Retrospective consensus has cemented the album’s status as a classic. Publications ranging from Pitchfork to NME have consistently ranked it among the greatest albums of the 1990s and beyond. While some contemporary critics like Robert Christgau found Smith’s work "tuneful if depressive," others, such as those at Tiny Mix Tapes, have argued that the songs on Either/Or represent the absolute peak of his songwriting craft.

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