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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.” 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."

Not really. I mean, I hear it's an old folk tale, the idea that someone could sell out. It's such a goofy stance. There's so much less money in music [today] that sometimes getting a car commercial is the only way that you're gonna make money. People don't make nearly as much money as they did in the '90s, so I think it was way more prevalent then. But also, who wants someone to just be lonely and be making records in their basement instead of collaborating with a band and touring and making sounds? I feel that way about it. It's lonely to make records by yourself. I hear a joy in the more jammy songs on this album.I think I'm one of those people you're describing: That's not a record that I've spent much time with, and maybe I was just too upset. It can be intense to go down certain rabbit holes with him. But Figure 8 is a record I don't consider as dark — it has its moments, but by and large it feels more like an exploration of his pop sensibility. When did you first encounter that one, and how did you make sense of it within the rest of his catalog?

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.

Lindsay Zoladz: I'm 33 now, so I was in high school when Elliott Smith died. I have a pretty vivid memory of it — I definitely wrote a really bummed LiveJournal entry that day. Since you got into his music after he was already gone, I'm curious about your earliest memories of listening to him, and what record you started with. Honestly, because I had an iPod, I pretty much shuffled everything, so all those records kind of blended together at first. But then, I got really into vinyl. I got all his records on vinyl and that's how I would listen for a long time; they each have a specific vibe and mood. The song " Son of Sam" I really loved right out the gates, because I've always been super fascinated with serial killers. I was like, "Oh my God — you can write about that?"