If you want to hear Elliott Smith’s anger, listen to Roman Candle. If you want to hear his eyewitness chronicle of Portland’s music scene at the height of the grunge era, his self-titled sophomore record does the trick. Either/Or is his last indie record, and XO is his first for a major label, with an Oscar nomination somewhere in between securing his strange legacy and providing a little more musical freedom. On those last two, you can hear the most essential aspects of Smith’s oeuvre congealing — specifically, the exorcism of childhood trauma through means both healthy (the act of making music itself) and less so (drug abuse and other self-destructive behavior) and his absolute love for the White Album. But nowhere do they come together to greater effect than on Smith’s fifth album (and final release before his violent demise), Figure 8, released 20 years ago this Saturday.

On its surface, Figure 8 is a placid, accessible listen. Its confident, Beatles-indebted melodies are imbued with the sunshine of Los Angeles, where Smith had recently relocated. But, written as it was during one of the most tumultuous periods of Smith’s too-brief life, there’s darkness at its center. It’s not the calm before the storm — it’s Smith in the eye of the hurricane, making his most brilliant work even as he veered completely off the rails.

At the time of its release, Pitchfork panned it; Ryan Schreiber himself all but called Smith a sellout while begrudgingly giving the album a 6.9. SPIN ran a similarly snarky review, billing him as the harbinger of the death of indie rock while placing him somewhere on a continuum with Frankie Valli, Billy Corgan, and George Harrison. Even more favorable reviews from the LA Times, the Guardian, and NME (which called it his best album to date) tempered their praise with grim caricatures of Smith as the patron saint of wet blankets, as though to admit they’d enjoyed these songs would somehow tank their cooler-than-thou critic clout.

Part of this was because Smith’s music was decidedly out of step with his contemporaries. Smith started out in the era of Kurt Cobain and Kathleen Hanna, when white dudes with acoustic guitars didn’t exactly move units unless they were on MTV Unplugged. As an opener for noisier acts like Sebadoh, Smith often fought to be heard over talkative, disinterested crowds in rock clubs. But when his music clicked with people — like Kill Rock Stars founder Slim Moon, Flaming Lips drummer Steven Drozd, Mike Doughty of Soul Coughing, or even members of Fugazi and the Beastie Boys — their awe was indelible, and many of Smith’s fans in the Portland scene became his closest friends and staunchest advocates.

Ironically, the sad-sack image Smith was saddled with was mostly the creation of mainstream journalists who tuned in just in time for “Miss Misery.” Despite his self-harming behavior — he didn’t really spiral into hard drug use until touring behind Figure 8 but was already drinking heavily, prone to bouts of cutting, talked often of suicide, and had even jumped off a cliff — almost everyone who knew him and is still willing to talk about it has said that he was a bit of a goofball, known to crack jokes or do weird dances for a laugh.

Dorien Garry, who became close to him while working as a publicist at Girlie Action — which handled press for Kill Rock Stars when Smith was at the label — noted that he “had a real thing about clowns” and was “fascinated” and “intrigued” by them. It wouldn’t be surprising if he identified with their ability to entertain, to paint on a face that would obscure whatever pain lurked underneath. But on “Can’t Make A Sound,” he eulogized that aspect of persona: It had been killed by the white-suited “hero” who performed at the Oscars, and he’s left “a ghost in every town” on his tour stop.

Figure 8’s title refers to an infinite loop created by the futile, repetitive pursuit of perfection that typified Smith’s musical ambitions. “That was what the title was supposed to suggest — a self-contained pursuit that potentially could be kind of beautiful and has no destination,” Smith told NME’’s John Mulvey at SXSW in 2000. “Like when figure skaters are skating a figure eight and they’re trying to make it just right. As soon as they stop they’re gonna fuck it up, cos they can’t get out of it without ruining it. I kinda like that.” More often than sadness, perfection — and unadulterated anger — was what fueled Smith to continue creating.

Even so, he was clearly exhausted by the responsibilities of major label album cycle promotion, having signed to Dreamworks Records in 1997 to record XO while simultaneously navigating the spotlight Good Will Hunting had thrust him into. Figure 8 is littered with tracks dissecting his newfound fame. “I heard you found another audience to bore/ A creative thinker who imagined you were more,” he sings on “Easy Way Out” as though chiding himself for his own accidental success. On “Stupidity Tries,” Smith reckons with imposter syndrome, musing “Got a foot in the door/ God knows what for,” waffling between apathy and disappointment. He posits himself as the titular character of “Junk Bond Trader,” marketing his own suffering to the masses.

And yet, the double entendres and metaphors Smith was so fond of using prevent him from sounding totally ungrateful for mainstream recognition. You could listen to any of these songs and relate — even if you weren’t an indie artist navigating major label success — because he built whole worlds around his burning critiques, populated by doctors, serial killers, soldiers, and unlikely saviors. “It’s less about me and more about what might be interesting about my situation,” he told NME. “The songs are like little movies that you can watch if you want, they’re not supposed to make people feel like I do.”

According to an interview with Rob Haynes of Louder Than War, Smith saw Figure 8 as “a dream diary… a record of imaginative situations. The lyrics do have some connection to my reality, or maybe someone’s reality that I know. It’s not meant to be a photograph of myself, a painting of me, but it’s not like total fiction either. It’s sort of in between.”

Smith was purposely dodgy in these interviews, particularly when it came to questions about his personal life. He hated the music industry machine, but his label, known as an advocate for artists, never attempted to stifle him, and he was more than happy to dig around in their deep pockets. He told SPIN in 1999: “I’m not interested in making ‘Elliott Smith records’ over and over again. I’d be really happy if I could write a song as universal and accessible as ‘I Second That Emotion.’ It’s a big game to play, trying to make something that’s mainstream enough and still human.”

Dreamworks head Larry Waronker was enamored of his talent, indulging Smith in his creative whims and helping execute his most grandiose ideas, hiring studio musicians to give both XO and Figure 8 their characteristically lush arrangements. (Smith still recorded the majority of instruments himself, double- and triple-tracking vocals and guitars as he had on previous albums.) Part of Figure 8 was even recorded at Abbey Road. Two interstitial instrumental pieces — “The Roost,” which is tacked to the end of the already indulgent saloon piano ballad “In The Lost And Found,” and the “Happiness” addendum “The Gondola Man” — are the result of friend and producer Rob Schnapf encouraging Smith to mess around with a Boomerang looper just to see what he would do with it.

It wasn’t until later, in a state of crack-induced paranoia, that Smith became convinced the label was spying on him, following him in unmarked white vans, breaking into his home to steal demos from his computer. On Figure 8 that persecution complex is mostly turned inward, its bitterness sharpened by his simple, understandable disdain for being touted as a tortured artist in every tired magazine profile that joked about his downtrodden image.

What Smith was fighting inside was much more insidious. He’d endured devastating childhood abuse at the hands of his stepfather from the time he was three until he was 14, when we went to live in Portland with his biological father; it’s been said that “Everything Reminds Me Of Her” redirects his guilt over leaving his mother Bunny behind in his escape to the Pacific Northwest into a the subtext of failed relationship fodder. His stepdad had recently written a letter of apology for the abuse (arriving suspiciously in the wake of Smith’s Oscar nod), and Smith suddenly found the vitriol of “Roman Candle” diffused and displaced. But he still felt the shame, rejection, and destroyed sense of self-worth so common in victims of the sort of trauma he endured.

As much as “Easy Way Out” seems like Smith reminding himself not to trust his label (“You’ll take advantage ’til you think you’re being used”) the next line is more indicative of the painful memories and attendant grief his success triggered (“Cause without an enemy your anger gets confused”). When he sings “The painting never dries” on “Stupidity Tries,” he hangs on that first syllable — “pain” — before finishing the line. And ultimately, “The silver lining in the corporate cloud” on “Wouldn’t Mama Be Proud?” turns to a cold rain when Smith admits how illusory it all is, that “postcards from the side of the road” are “photographs of moving parts about to implode.”

Much of Smith’s back catalogue reckons with his abusive past, even examining his destructive attempts to numb it. And yet, Figure 8 seems to be the record where, due to outside pressures and newfound attention, every bad feeling and painful memory he still needed to confront boiled to the surface. Album opener “Son Of Sam” isn’t about David Berkowitz; it’s about Smith knowing he’s a sore thumb, about his inability to make relationships work. He turns it around on searing kiss-off “Somebody That I Used To Know,” trying to convince himself he isn’t the damaged one. But “I Better Be Quiet Now” sees Smith burning all of his professional and personal bridges almost compulsively, especially those relationships built around both.

He knew he had a long way to go to heal, but he was constantly fighting the tendency to shut down: “I better be quiet now, I’m tired of wasting my breath/ Carrying on, getting upset/ Maybe I have a problem/ But that’s not what I wanted to say/ I’d prefer to say nothing.” On the track, he swears he’s not lonely — he can play all the parts, and it might sound like he’s got a full band behind him. But at the end of the day, he’s alone in a room, with dark thoughts circling.

And that brings us to the emotional void at the center of this record, “Everything Means Nothing To Me.” According to David McConnell (who recorded a good chunk of the posthumously released From A Basement On A Hill), Smith wrote the song during a psychotic break, with blood streaming down his arm as he sat at the piano, having carved the word “NOW” into his flesh. There’s also a rumor he wrote it while on mushrooms; maybe both things are true, and maybe neither of them are. The song starts out with just piano and a little vocal reverb, cascading piano punching up the dire ambivalence of its central mantra. And then suddenly there’s this clatter of drums and wash of airy strings, as if Smith’s indifference was his only freedom from the pressure of the future, the pain of his past, and the absolute black hole their collision had created in his psyche during the writing, recording, and release of Figure 8.

When it ends, there’s only the opening riffs of “L.A.” Instead of populating it with the sycophants of earlier takes on the City Of Angels like “Angeles” and “Bled White,” Smith finds comfort in, of all things, the nice weather. There’s no hint of irony when he sings “Morning had to come/ I’d be walking in the sun/ Living in the day/ But last night I was about to throw it all away.” He takes a similar approach on “Happiness”: “What I used to be/ Will pass away and then you’ll see/ That all I want now/ Is happiness for you and me.” Smith had a love/hate relationship with LA that informed a lot of Figure 8. “It’s the last place I thought I’d ever live, but that was part of the attraction,” he told NME. “I like to move, and I like being close to the thing I don’t like. It’s good to have something that makes you a little mad and keeps you thinking about something other than yourself. That keeps you focused outwards.”

The now-iconic cover art for Figure 8 forever links Smith to the city where he would perish four years later in an apparent suicide. He stands in front of a graphic mural at 4334 Sunset Boulevard, formerly the home of Sound Solutions Audio. It was taken by Autumn de Wilde, who formed a friendship with Smith in the late ’90s and shot the music video for “Son Of Sam.” She had gone to junior high down the street from said mural, and remembers girls getting beat up in the parking lot of the nearby McDonald’s. The wall, which immediately became a memorial to Smith upon his death, has barely survived the morphing Los Angeles landscape despite calls to preserve it; it’s been graffitied, restored, and partially demolished at this point.

Ten years after Smith’s death, de Wilde told Pitchfork: “My relationship with that Figure 8 wall now is conflicted. Not because I have any grievances about it, but it was my wall that nobody cared about, you know? It’s so awesome that people are repainting it, but it’s burned in my head — this mural from childhood — so I can’t help but think that they painted it wrong. I don’t mean to sound like an asshole. I just mean they didn’t reproduce it exactly the same, so for me it’s like a weird blip, an awkward thing to look at because my eyes are trying to correct it.”

When we look back on Elliott Smith’s life, we all want to correct the vision, wishing things had played out differently. On a longer timeline, he may have achieved some semblance of healing — and of course, there would be more of his music. At the end of his life, he was recording what would become From A Basement On The Hill, and while it offered some comfort, we’ll never know what his fully realized vision of the album sounded like. We do have Figure 8 though, and in my mind, it will always represent Elliott Smith at his most potent. It combines that Roman Candle fury with a seething referendum on the music industry, rails against abusers of all kinds, pays homage to the Beatles, and desperately looks for solace whatever way Smith could find it — letting go, giving up, or simply walking around in the daylight.