About two minutes into Either/Or opener “Speed Trials,” Elliott Smith’s seamlessly double-tracked lead vocal splits into a two-part harmony. It’s a very subtle gesture, and only lasts for a few seconds—but contrasted with the tight, hushed unison of Smith’s prior solo output, it feels as dramatic as The Wizard of Oz shifting from sepia to technicolor. This moment plays out like a microcosm of Either/Or at large, the sound of Smith conjuring something far bigger than himself and coming into his own as a songwriter, arranger, and performer. The final album in Smith’s catalog before the major label-backed XO and Figure 8, Either/Or marks the last time Smith’s instincts would outpace the studio resources to execute them. It's extraordinary how he embodies a magical, alchemical mix of intimacy and bombast.

By the time Either/Or was released in 1997, Smith was no stranger to the cynical machinations of the post-grunge major label gold rush. A year prior, his former band Heatmiser had been put through that very ringer, an experience captured in Either/Or standouts “Pictures of Me” and “Angeles.” Either/Or sounds like the work of somebody who has zero interest in either conforming to or directly transgressing the “commercial” sounds of the day. It’s too ambitious to read as “lo-fi” and too gritty to read as straightforward pop classicism. Thankfully, this 20th anniversary remaster doesn't smooth out too many of those rough edges—if anything, it brings the unique sound of the record into even clearer focus.

The sounds and words of Either/Or often conjure very specific images, textures, and situations. And yet, Smith—as with many truly great songwriters—used this specificity as a way to explore emotional themes that resonate both deeply and broadly. Nowhere is this clearer than “Between the Bars,” the closest thing to a modern-day standard Smith ever wrote and covered by everyone from Metric to Madonna. It’s not a love song, exactly, and it’s not a song about addiction, exactly. “Between the Bars” is about the ways in which protecting somebody you love turns into the need to control that person. The fact that Smith was able to build this much emotional complexity into a song that sounds at home in a stadium or at a Starbucks speaks to his irreplaceable gift as a songwriter.

Elsewhere, Smith amplifies his well-honed songwriting chops with more fleshed-out arrangements. “Ballad of Big Nothing” propels itself forward with bubbly McCartney-esque bass lines and background vocals that sound like they might have been string arrangements if there were an orchestra handy. “Angeles” and “Cupid’s Trick” provide a back-to-back study in Smith’s versatility as a guitarist, going from intricate fingerpicked pattern to lopey electric riffs. By the time album closer “Say Yes” rolls around, it’s clear that the solo acoustic approach is a specific and purposeful choice, and no longer Smith’s default mode.

This reissue is framed as an “expanded” edition, and the bonus materials included fit the bill nicely. Rather than aiming for comprehensiveness or definitiveness, the bonus tracks provide interesting glimpses into Smith’s growing strength as a live solo performer (some excellent live recordings of album and non-album cuts), sense of humor (a sketch of New Moon track “New Monkey” that sounds like it was played on a baseball organ), and where he would go with his next record (a formative version of XO cut “Bottle Up and Explode!” that shows just how much thoughtful editing and revision went into the final version). And then there’s “I Figured You Out,” a longtime fan favorite that Smith gave to his friend Mary Lou Lord to record because it “sounds like the fuckin’ Eagles.” “I Figured You Out” would have been the most straightforward and polished song on Either/Or, and its omission speaks volumes about how determined Smith was to find his own voice and chart his own path.

In the years that followed the release of Either/Or, Smith managed to do just that, performing “Miss Misery” at the Academy Awards and releasing an uncompromising major label debut. For some of his fans, Either/Or marked the end of Smith’s career as a direct and intimate folk singer-songwriter. For others, Either/Or marked the beginning of Smith’s career as a one-man classic pop band. In truth, Either/Or marks the one moment in Smith’s career when he was truly both.