Welcome to 1999 Music Week, a celebration of one of the most interesting, vivid, varied music years ever. Join us as we count down the best singles and albums of the year, remember the days of scrubs and the girls who wear Abercrombie & Fitch, and argue about which albums stood above the rest.

In 1994 Stephen Malkmus declared: “Good night to the rock ’n’ roll era.” And he was right, of course, but he didn’t factor in the death throes. It would take a final handful of hospice years filled with spasms and Strokes for the genre to finally succumb fully to demographic destiny and terminal stasis. Quite accidentally or quite by design, Wilco was one of the few bands that clambered aboard the genre’s final chopper out, just as the curtain dramatically fell on rock’s imperial phase.

The Ringer’s 40 Best Singles and Albums of 1999 1999 was one of the most interesting music years ever. We’re celebrating that by definitively ranking its top songs and albums, 20 years later.

Jeff Tweedy’s new band Wilco signed to Reprise Records in 1994 following the dissolution of the great, fractious cowpunk outfit Uncle Tupelo. Wilco started out as offhand and irreverent as they would later become detail-oriented and disciplined. Their initial release, A.M., came out in 1995 to cheerful reviews and underwhelming sales. It was ramshackle, charming, and a low-stakes hangout record on the order of Bob Dylan’s New Morning. It’s aged well, but the contemporaneous lack of public enthusiasm made the band an uncertain prospect for their major-label overlords. Tweedy had often been perceived as second among equals next to his rival and former Uncle Tupelo bandmate Jay Farrar, and when Trace, Farrar’s first solo outing as Son Volt, yielded wild acclaim and even a minor hit single, “Drown,” it further deepened the impression of Wilco as a likely industry also-ran.

Wilco responded to the disappointment with the energetic industriousness of the Midwest unionists they are and forged 1996’s unstoppable double LP tour de force Being There, which stretched the band’s musical muscles from Dwight Twilley–worthy power pop to Workingman’s Dead–style cosmic ruminations. Being There massively outperformed expectations, sold nearly twice as many copies as A.M., and made Wilco a minted commodity with a rabid following.

Then they got gloriously weird. Wilco’s third LP, Summerteeth, is a dense and disturbing record, a metaphysical and emotional bloodletting with a palpable menace lurking just beneath its confectionary surface. Lushly recorded at Willie Nelson’s studio in Spicewood, Texas, its tales of debauchery and betrayal are carried along by swooping synths and candy-colored harmonies.

Gone are the country and Creedence Clearwater Revival references which had characterized Tweedy’s work for a decade, replaced by panoramic, Phil Spector–ish flourishes. Indeed, one of the few records in the tradition that serves as precedent for Summerteeth is Leonard Cohen’s oddball 1977 classic Death of a Ladies’ Man, which wed the songwriter’s fatalistic musings to Spector’s maximalist production to phenomenally bizarre effect. On Summerteeth’s indelibly bouncy opening track and initial single “Can’t Stand It,” bells chime and keyboards soar as Tweedy spirals into a full-fledged existential panic: “No love’s as random / as God’s love!” The surfeit of hooks seem somehow to mock his terror and misery.

Another of Summerteeth’s obvious antecedents is Big Star’s Sister Lovers, the haunted 1978 sign-off from the legendary outré icons. That masterpiece of moody dolor and vaulting melody hangs heavily over the creeping hellscape of Tweedy ballads like “She’s a Jar” and “Via Chicago,” two tracks whose chillingly offhand references to emotional and possibly literal violence are among the most disturbing to ever appear on a rock album.

If Tweedy sounded unhinged, it was hardly an act. Weary from touring, and increasingly in the grips of a severe opioid addiction, his deteriorating state mirrored the extreme boomerang between tracks like the addled-but-life-affirming “Nothing’severgonnastandinmyway (Again)” and the distraught-hotel-room-suicide-note-doo-wop of “Pieholden Suite.” He was not well, and neither was his chief collaborator, the multi-instrumentalist Jay Bennett who would serve as Wilco’s second-in-command during their classic three-album run of Being There, Summerteeth, and Yankee Hotel Foxtrot. Mutual enablers in the best and worst sense, Tweedy and Bennett bonded over drugs and dramatic soundscapes to beautiful but unsustainable effect. The partnership would run its course by 2001 and Tweedy would eventually get sober. Bennett would not, and he suffered a fatal overdose at the age of 45 in 2009.

In the late 1990s, a vogue for ’60s nostalgia permeated rock music’s hipper circles, ranging from Elliott Smith’s heart-on-sleeve McCartney-isms to the Flaming Lips’ acid-drenched psych-redux to the historical recreationist lo-fi of groups like Olivia Tremor Control. While Summerteeth’s throwback aesthetics positioned it as a part of that wave, perhaps the album’s finest virtue was the integration of nostalgic reference points with modernist and avant touches, signaling a working knowledge of the canon and a willingness to alchemize its elements into something daring and novel.

Here, the wheezing synths and Krautrock chug of “I’m Always in Love” suggests the Beach Boys (by way of Wire’s) “Ex Lion Tamer.” The woozy tropicalia of “How to Fight Loneliness” is like a narcotized Os Mutantes fronting Raymond Carver, and the winsome-until-you-read-the-lyrics title track is a sunbaked ditty about domestic bliss that turns into a literal and figurative nightmare: Loudon Wainwright III backed by the Wrecking Crew. Tweedy, always an exemplary vocalist, has never sung better. He buttresses the supple swing of “When You Wake Up Feeling Old” with a light touch reminiscent of Van Morrison circa His Band and the Street Choir while “ELT’s” razor-wire riff is elevated to majestic heights by a keening Nick Lowe–like croon. Many other acts of the era were pulling from similar influences, but Summerteeth does far more than rearrange the cultural furniture. It remodels the whole house into something beautiful and scary.

In this regard I have always found Summerteeth to be the overlooked predecessor to 2002’s much-obsessed-over Yankee Hotel Foxtrot—the Revolver to YHF’s Sgt. Pepper’s as it were. While the latter release would be immediately (and justifiably) lionized for its operatic sweep and zeitgeisty air of post-9/11 paranoia, it was more of a refinement of Summerteeth’s wild innovations than a groundbreaking development on its own terms. Summerteeth is something different entirely: unwieldy and unsparingly catchy, futuristic and familiar, a spiritual knife fight held in a circus fun house. Wilco has gone on to make great records for decades, cementing Jeff Tweedy’s well-earned reputation as one of our finest and most indispensable songwriters. But they never made a better one than Summerteeth, the best record of 1999.

Elizabeth Nelson is a Washington, D.C.–based journalist, television writer, and singer-songwriter in the garage-punk band the Paranoid Style.