“I dreamed about killing you again last night, and it felt alright to me.” That’s a hell of a way to begin a song, and a hellish way. Just when the sleepy acoustic guitar chords out front of “Via Chicago” have lulled you into a stupor, Jeff Tweedy arrives to announce his shrugging approval toward the prospect of murdering someone he loves.

Eventually the Wilco frontman moves on to increasingly abstract imagery, from “I painted my name on the back of a leaf/ And I watched it float away” to “And crawling is screw faster lash/ I blow it with kisses.” The song builds from those initial chords into a vast soundscape that encapsulates Wilco at their best — that unparalleled ability to pile layers of beauty onto a simple folk song and then artfully rip it to shreds. At climactic moments, Tweedy launches into a slipshod guitar melody like Stephen Malkmus soloing over a disintegrating memory. Following it through to the finish is thrilling, but to get there you have to endure a whole verse of bloody, explosive details. It’s no wonder Tweedy writes in his new memoir Let’s Go (So We Can Get Back) that the album containing “Via Chicago” is “the record that’s hardest for my wife to listen to.”

Summerteeth, released 20 years ago this Saturday, is Wilco’s contribution to a common trope in pop music history: The prettiest songs are often about the ugliest subjects. It comes up sometimes when discussing the work of Elliott Smith. Eva Hendricks from Charly Bliss has invoked it during the rollout for the band’s upcoming Young Enough. “Hey Ya,” “Semi-Charmed Life,” “99 Luftballoons” — three infectious bops about a breakup, drug addiction, and nuclear war respectively. Summerteeth exists as part of that lineage. It’s the most gorgeously ornate album Wilco ever made, and also the most disturbing.

Tweedy wrote the songs that became Summerteeth at what should have been the happiest time in his life. Rather than sabotaging his music career, the breakup of Uncle Tupelo — his massively influential country-punk partnership with childhood friend Jay Farrar — had liberated him to pursue a vision entirely his own. He’d married his longtime girlfriend, Sue Miller, the owner of Chicago music venue Lounge Ax, and together they were raising a young son. The 1996 double-LP Being There had established Wilco as arguably the most talented and ambitious band in alt-country and helped Tweedy escape his reputation as Farrar’s plucky sidekick. His career was on the rise, his family life settling down.

Yet he writes, “I was probably as unhappy as I’d ever been. I was insecure, homesick, and drug-addled.” Even worse, “I had more love in my life that I’d ever had, and I was still lonely.” Furthermore, Tweedy was frustrated that Wilco had been pigeonholed as an alt-country band, a perception reinforced by Mermaid Avenue, a collaborative album with Billy Bragg setting music to unused Woody Guthrie lyrics. Being There had blown open the possibilities of what Wilco could be, but most of the listening public still saw the band a certain way. “People assumed we had this sort of identifiable, philistine range of influences,” Tweedy wrote, “and we, in our heads, knew that wasn’t the case.”

To upend those expectations, Wilco made their idea of a bubblegum record. The rootsy pop-rockers and ballads that populated 1994 debut A.M. were still in the mix, as were the formal and stylistic experiments that made Being There such a leap in terms of breadth and quality. But now Tweedy and sideman Jay Bennett were building these songs into small-scale symphonies: Beach Boys harmonies spilling into every chorus, waves of gorgeous orchestration surging in and out of the frame. By this point they were more chamber-pop than cowpunk or whatever term the readership of No Depression favored that week. One of the leading lights of this gritty, doggedly authentic movement had crafted a hyperreal fantasia, albeit one tinged by the dreariness of regret. Or as Tweedy sang on “A Shot In The Arm”: “What you once were isn’t what you wanna be anymore.”

It was a different record born from a different process. In many ways Summerteeth was a dry run for Yankee Hotel Foxtrot and its accompanying saga, be it Tweedy’s embrace of abstract, impressionistic lyrics, the introduction of extensive studio tinkering to tear apart the songs, or the tearing apart of the band that came along with it. Drummer Ken Coomer and bassist John Stirratt were largely excluded from the sessions while Tweedy and Bennett popped pills and piled on the overdubs. As Coomer complained to Greg Kot in his Wilco biography Learning How To Die, “There wasn’t really a band, just two guys losing their minds in the studio.”

It’s hard to dispute the results — Summerteeth continued a run of masterpieces that began with Being There and continued well into the next decade — but Reprise Records did anyway. That’s another way the album presaged Yankee Hotel Foxtrot: The label asked Wilco to go back and record more accessible music to promote to radio. In this case the band played along, leading to a rare instance of label meddling that worked out really well. The glorious guitar-pop onslaught “Can’t Stand It” is a phenomenal album opener and a frankly underrated entry in the Wilco canon. Still, although you can see why the label didn’t want Summerteeth to begin with the drowsy, depressive, dysfunctional “She’s A Jar,” it’s tough to understand why they couldn’t find a single anywhere else on the tracklist — especially when they had one readily available just one track beyond “She’s A Jar.”

On one hand, there’s nothing quite like “A Shot In The Arm” in Wilco’s discography. On the other hand, it’s a great case study for what Wilco were doing on Summerteeth: one of the most beautiful and exhilarating pop songs they’ve ever recorded, and also one of the bleakest. Bennett’s cascading piano ripples, a rock-steady Coomer backbeat, and a Stirratt bass line worthy of Este Haim’s “bass face” propel it breathlessly forward while an arsenal of squealing synths collide in the sky like fireworks. All the while, Tweedy alludes to strained relations with his wife and seemingly considers whether a heroin habit might jolt him out of his doldrums. It begins and ends in flicker of synthesizers.

He hints at those tensions again on “Pieholden Suite,” a lush multi-part sequence that really earns that “suite” designation: “There’s a whisper I would like to breathe into your ear, but I’m too scared to get that close to you right now.” And again on “We’re Just Friends,” with its zen koan lament, “If love’s so easy, why’s it hard?” And again on the heartbreaking “How To Fight Loneliness,” a lounge-ready acoustic slow-drift that concludes the best strategy for battling alienation is “just smile all the time.” Punchy rock tracks “I’m Always In Love,” “Nothing’severgonnastandinmyway (Again),” and “ELT” course with stress and frustration beneath their cheery veneers. “Can’t Stand It” toggles between strutting Stones-lite verses with a carefree party vibe and a euphoric chorus smothered in keyboards and church bells, yet Tweedy spends the song lashing out at the randomness of both God’s love and his own. Yet again, he evokes a personal life that’s falling apart: “You know it’s all beginning to feel like it’s ending.”

Not everything on the album is so dark. Summerteeth concludes with a stretch of music that feels like a redemption arc. There’s real tenderness in the lullaby “My Darling” and the lazy back porch reverie “When You Wake Up Feeling Old.” The title track finds some kind of resolution as it breezes from snappy twang to sighing rhapsody, though even the apparent reconciliation is oblique enough to keep listeners guessing. And on gentle closing track “In A Future Age,” Tweedy buys into the possibility of change, bookending his album-opening cries that “Your prayers will never be answered again!” with a call to “turn our prayers to outrageous dares.” Yet despite things generally looking up at the end, the album remains a document of Tweedy at one of his lowest moments.

He writes in his memoir that the darkness explored on Summerteeth, while very real, was not autobiographical in the strictest sense. He discusses writing “Via Chicago” and other songs from the era in a fragmented style he compares to mosaic and collage. “When I write in this mode, I write for myself first, pretending that the audience isn’t even there, and will never be there,” he explains. “I can get things off of my chest, I can invent versions of myself that are better than I believe I am … or worse, are even downright awful and murderous. I can expose shadow selves that I believe I should keep my eye on. I can admit things about myself without really having to take ownership of anything.”

In other words, when “She’s A Jar” reaches its twist ending and Tweedy declares, “She begs me not to hit her,” he’s not actually confessing to domestic violence. He’s singing about a fictionalized version of himself, or maybe as a different character entirely, as a way to air out the more disquieting corners of his psyche. Which is not to say it’s wrong to be repulsed by these images or to wish that Tweedy, as the album’s ostensible protagonist, had not verbalized them. There are parts of Summerteeth that practically require a trigger warning. Tweedy almost certainly wants you to recoil, and maybe to reckon with the part of yourself that identifies with the grisly impulses. As a teenager who discovered the album after obsessing over Yankee Hotel Foxtrot and working backwards, I don’t think I sensed the gravity of those words. Returning to them as an adult is sobering, even as someone for whom this album is basically scripture. You live some life, and a song can level you all over again for entirely new reasons.

In some ways, the grotesque self-reflections on Summerteeth are not dissimilar from the ultraviolent fantasies Eminem was spinning around the same time or the “I thought about killing you” monologue that opens Kanye West’s Ye. Except Eminem was attempting to shock and provoke, and Kanye seems to believe any thought that emerges from his brain is a good thought, no matter how deranged. (“Just say it out loud to see how it feels.”) Unlike those guys, Tweedy wasn’t glorifying that part of himself, and to call it exploitation feels like a stretch. He never seemed to relish revealing his dark side, like a kid who’s getting away with something. It was more like he had to articulate his potential for evil as a means of accountability. It strikes me as significantly different, a form of radical vulnerability that accurately reflects our broken human condition. Still, in the harsh light of 2019, if your reaction to these lyrics is, “Ugh, another man singing about hurting women,” who could blame you?

For that reason and many others, Summerteeth occupies a weird space in Wilco’s history. It stands alone among their output, a product of personal crises and creative friction that would have ended the band if they’d carried on forever. There are people who’ll (wrongly, but earnestly) tell you that actually, this is the best album Wilco ever made. Others see it as the beginning of the end of the band they once loved, or a rough draft for future glories. Whatever you make of Summerteeth, I can attest from experience that the album helped Wilco to become for a generation of listeners what the Clash and the Minutemen had been for Tweedy. Immaculate yet messy, tragic yet hopeful, it was a doorway to possibility for others who, like Tweedy, were fumbling toward some greater version of themselves.