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When Either/Or originally came out at a time when grunge was still big, Sugar Ray and Smashmouth were hitting the charts alongside the Spice Girls and the Notorious BIG, but Smith created a subtly devastating album using nothing but pretty guitar chords, carefully crafted chamber-pop arrangements and intimate lyrics. The album has made a lasting impression on musicians and music fans across all genres – even Frank Ocean mentioned Smith’s influence in the liner notes to Blonde – and his fanbase continues to grow. Real, perhaps, because it was so deeply rooted. Born Steven Smith into a family from the Community Of Christ church, a Mormon denomination, he was only six months old when his parents split. His mother married an insurance salesman named Charlie Welch, whom Smith would claim first beat him on their wedding day, aged three. His memories of his childhood had always been hazy, but at 14 he left his mother’s home in Texas to live with his father in Portland. “I didn’t sleep at all for about the first six months I lived there,” he told Under the Radar. “I was very worried about my mother.” In another interview, he elaborated: “I couldn’t stay in the same house as my stepfather.”

Smith soon left Portland for Brooklyn, characteristically low. His New York roommate Dorien Garry told Spin: “He always talked about suicide… He made me promise that I wouldn’t be mad at him. He just talked about it as if it were going to happen.” Cannon – and many, many other people – feel like Smith’s music spoke to him directly, like a secret that was for his ears only. “Because of the way he talks about things that are going on, and because of who he is, you feel like you know him through his music,” said Cannon.It's kind of hard for me to believe this album is 20 years old, because in a lot of ways it still sounds very fresh. Do you think it would find an audience if a record like this were released today? Totally — maybe even more than XO , this is the record of his that I associate with inventive production choices just as much as I do great songwriting. From a production standpoint, are there elements on this record that have inspired your own music directly? Shortly after the release of his fifth studio album, Figure 8 — the last record he'd finish in his lifetime — Elliott Smith told a Boston Herald writer why he was so drawn to that titular image. "I liked the idea of a self-contained, endless pursuit of perfection," he said. "But I have a problem with perfection. I don't think perfection is very artful. But there's something I liked about the image of a skater going in a twisted circle that doesn't have any real endpoint. So the object is not to stop or arrive anywhere; it's just to make this thing as beautiful as they can."

That's perhaps the greatest comparison Smith could have received. His adoration of the Fab Four bookended his life and career: He once claimed that the first record to ignite his desire to be a musician, when he was just 5 years old, was the ambitious and playfully eclectic White Album. ("It was pretty much my inspiration, that and AC/DC," he said in an interview the month before Figure 8 was released.) Much later, in those troubled days of 2003, the final song he ever played live was a cover of the haunting White Album cut "Long, Long, Long." That a young talent like Bridgers would call him her hero — and mention him in the same breath as his heroes — evokes that Autumn de Wilde image on the cover of his magnificent 2000 album. Maybe he never got to see that colorful continuum of music that snakes out behind him. But plenty of us can still hear it. In the wake of the Oscars, Smith signed with DreamWorks Records, but Schnapf feels the press and radio “game” that ensued played further on Smith’s insecurities. “It’s a double-edged sword of wanting to do what’s being asked of you and really hating what’s being asked of you and not being good at it, in that he’s real, he’s not a bulls*** artist.” Dreams and grievances, biography and metaphor, truth and fiction—it all swirled together in Smith’s music until every throwaway line seemed like a secret. Smith fans were spooked into lifelong identification because of the purity of that voice, its unmistakable sadness, its seeming simplicity. But the deeper you peered into Smith’s music the more elusive and diaphanous the portrait of “Elliott Smith” became. Behind “Elliott” was, always and forever, Steven Paul Smith, the guy behind the guy behind the guy who had been working out his childhood songwriting visions for a lifetime and arrived at a point in which his ambitions and his talent synced up in one tall, clean line. The “Elliott Smith” of Smith’s solo records was not a person; it was a project. And XO was a testament to how far that project could go. Up until then, Smith was known for playing music so quiet it almost died away before it reached your ears. He made most of his first three albums in friends and loved ones’ bedrooms, and it was his 1993 debut Roman Candle, which he recorded in then-girlfriend JJ Gonson’s basement by pressing his guitar strings against a low-quality microphone, that transfixed Luke Wood, DreamWorks’ A&R. The thought of Smith singing over a full orchestra might’ve seemed as unlikely in that moment as collaborating with Metallica.

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While he has clearly influenced music supervisors, it’s hard to underestimate the extent of Smith’s influence on musicians themselves. Smith’s music continues to affect people and shape musicians’ output. “I’m still surprised when I hear post-Elliott Smith things, like wow he really influenced a lot of people,” said Tony Lash, a high school friend and former bandmate of Smith’s. “What makes Elliott’s music so interesting is its attention to detail – in the lyrics, in the composition and in the production,” says Sadie Dupuis, from Speedy Ortiz and Sad13. “He had an uncanny ability to pepper introspective emotional observations with visual, evocative props.” Seemed like he went pretty all-in,” Schnapf sighs, sadly. “Up until then he didn’t smoke weed, he didn’t do drugs. A lot of Figure 8 was very positive. It just started to slowly unwind… Towards the end of the process there was skittish behaviour, not looking you in the eye kinda stuff. It seems like everybody hits this point in your late twenties or early thirties where however you’ve been dealing with shit stops working. Either you start to get your shit together or go heavily down the other way. He hit that fork and went the other direction.”