At the time of its release in July 1995, Elliott Smith’s second solo LP was at odds with the world as Nirvana had left it: In a crowd of loud, abrasive alt-rock bands—like his own, Heatmiser—there was something radical about sitting alone with an acoustic guitar, whispering when everyone else chose to scream. That Smith felt compelled to do it despite Heatmiser’s ongoing ascent—and despite a fear that his “head would be chopped off” by audiences so attuned to grunge, as he put it in a late interview—speaks to the conviction you hear throughout Elliott Smith. This wasn’t the sound of a side project or an experiment—it was the future. Heatmiser would break up the following year. More considered than 1994’s Roman Candle but more fragile than 1997’s Either/Or—his masterpiece—Elliott Smith is the late singer-songwriter’s first fully realized statement as a solo artist, and what he eventually deemed his darkest outing. Self-recorded on an eight-track tape machine, in the homes of friends in Portland, it’s often little more than guitar and Smith’s voice, but its melodies and song structures contain multitudes. At once beautiful and brutally, inescapably, unrelentingly sad, it’s an album that touches on themes and characters that would appear in Smith’s songbook up until his death in 2003—from child abuse (the venomous “Christian Brothers”) to isolation (“St. Ides Heaven,” which features a rare second vocal from The Spinanes’ Rebecca Gates) to suicide (“The Biggest Lie”) and addiction (“The White Lady Loves You More”). On the lone single “Needle in the Hay”—which famously soundtracked a suicide attempt in 2001’s The Royal Tenenbaums—Smith sketches a portrait of a junkie, at one point mimicking the hiss of heroin as it cooks. “I can’t be myself and I don’t want to talk,” he seethes. “I’m taking the cure so I can be quiet wherever I want.” Though it would receive more notice from fellow artists—Beastie Boys, Fugazi, and Sebadoh among them—than anyone else outside of Oregon, it became an important mile marker in a stretch that culminated with Smith onstage at the Oscars just three years later, in a white suit, playing Good Will Hunting’s “Miss Misery” to an audience of millions.