After the modest but surprising interest in Elliott Smith’s solo debut, 1994’s Roman Candle, the musical life of the 25-year-old singer-songwriter became evermore bifurcated. He’d spent much of the decade in Heatmiser, a rock band swept by the colossal wave of grunge to major-label heights. But as tension increased inside the band, and Smith drifted away from Heatmiser’s storming material, he increasingly focused on his own intricate and delicate tunes: Acoustic transmissions of addiction, ostracization, and emotional upheaval that were every bit as gorgeous as they were pained. In the throes of obsessive productivity, Smith was suddenly in the midst of a rare and remarkable outbursts of songs—the kind of creative streak that Bob Dylan had experienced in the 1960s, and that Joni Mitchell had found during the 1970s. The fruits of Smith’s songwriting blitz are on full display on his self-titled sophomore album, released in 1995. Earlier that year, Smith had relocated to the home of his friend Leslie Uppinghouse, setting up in front of an 8-track in the small room with high ceilings that doubled as her office and studio. Smith was nervous about Heatmiser’s contract negotiations, and how it might affect his own solo work, but he got to work anyway. He already had one song in the can—“Needle in the Hay,” which he’d recorded with a friend in 1994. It’s a haunted but graceful examination of codependence, as well as of the ends to which we can go to sate our demons. That song became the template for the new album, in which Smith’s intricate fingerpicking and patient strums—as well as his slightly dissonant tunings—are used to create vulnerable portraits of characters on the fringe: The drunk with nowhere to go but down (“Clementine”); the insomniac enduring endless existential anxiety (“Satellite”); the person who needs chemicals more than validation (“St. Ides Heaven”). These are exquisite and heartbreaking images from the lip of the abyss. There’s also a deep vein of empathy in these songs, as Smith admits his own damage and reckons with the fact that most people are dealing with their own disasters. He sings about his stepfather’s mistreatment on “Christian Brothers” and about his tough childhood in Texas on “Southern Belle”—both songs revealing the rotten architecture of his own current woes. “Everyone is a fucking pro/And they all got answers from trouble they’ve known,” he and Rebecca Gates sing during the final verse of the stunning “St. Ides Heaven.” Give people the space to figure life out for themselves, he asks—or at least give them space to try.