With the release of their second album, 1994’s Crooked Rain, Crooked Rain, Pavement seemed poised to become the next Nirvana—or at least a cooler, funnier, unrulier R.E.M. They conceded to releasing videos that could actually get played on MTV and lollygagged their way through a “Tonight Show” appearance, but their ambivalence to join the raging alt-rock revolution was made plain by album highlight “Range Life.” It used the most uncool sound at the time (throwback ’70s country rock) as a platform to take shots at the biggest bands at the time (Smashing Pumpkins, Stone Temple Pilots). To fans, “Range Life” was a form of quiet, casual protest against the increasingly homogenized world of post-Nirvana alt-rock; to detractors, it was proof of indie rock’s inherently elitist disdain toward the tastes of common people.

In a SPIN interview from April 1994, lead singer Stephen Malkmus revealed that, actually, both sides had it wrong. “‘Range Life’ is supposed to be a person from the ’80s country-rock era, like Lone Justice or Dream Syndicate, not being able to keep up with what’s going on today,” he said. “It’s not a really a diss on [Smashing Pumpkins and Stone Temple Pilots]. It’s more like, ‘I don’t understand this MTV world.’ Like Brian Wilson’s ‘I Just Wasn’t Made For These Times.’”

Here was Malkmus, at the very peak of his hype, forging a spiritual kinship with an obscure subgenre of a previous generation that had been deemed unfashionable by the shifting cultural tides. Maybe he knew that it would only be a matter of time before he’d find himself in a similar position.

The next year, Pavement’s infamously difficult Wowee Zowee doubled down on their refusal to conform to the modern-rock marketplace—a possibility that seemingly died for good the moment the alt-bros started hurling mud bombs onstage during one of their Lollapalooza sets that year. But surprisingly enough, the crisp, crystalline follow-up, 1997’s Brighten the Corners, had all the markings of a concerted crossover bid. And where Pavement’s earlier albums spawned a hundred sloppy ’n’ sarcastic indie bands in their misfit-preppie image, by ’97, their influence was impacting the biggest rock acts in Britain.

Blur’s Graham Coxon famously credited Pavement with inspiring his band to ditch Britpop for lo-fi noise on their caustic 1997 self-titled release. Elastica’s Justine Frischmann—then in the process of dismantling her own band’s pop appeal—became Malkmus’ duet partner and London crash-pad host. And though they seemed to exist in a completely different aesthetic universe at the time, Radiohead were professed fans, too. Pavement had gone mainstream, if only by proxy. But the indie culture that they once epitomized and still very much inhabited was rapidly shifting away from their brand of wry, off-kilter fuzz-rock, toward sensitive singer-songwriter expressionism and dramatic post-rock impressionism. The country-rock cosplay fiction of “Range Life” was slowly becoming their reality.

So for a group that always sounded torn between playing ball and throwing the game, Pavement’s fifth album, Terror Twilight, was a suitably conflicted, ambiguous document of a band that wasn’t sure if it was ready to break big or break up. On the one hand, it presents us with a group that still hadn’t completely given up on the idea of expanding their cult—for the first time in their career, Pavement hired a big-time producer to take a more hands-on approach in reining in their stray slack. On the other hand, Pavement hardly resembled a hungry band with their eye on the prize.

From Stockton, California (where Malkmus formed the band with childhood friend Scott “Spiral Stairs” Kannberg) to the University of Virginia (where Malkmus befriended percussionist/band mascot Bob Nastanovich), to New York (where superfan-turned-bassist Mark Ibold and Nastanovich’s old drummer pal Steve West came into the fold), the logistics of Pavement were always a challenge. By the late ’90s, all five members were living in different states spread across the country; the simple act of getting a practice together often required calling a travel agent. At a certain point, Malkmus wondered if all the frequent-flyer miles were worth it.

Following a long Brighten the Corners PR campaign that left him “pretty fried,” Malkmus told Rolling Stone that maybe it was time for the band members to lay down some roots, sparking whispers of a breakup. After settling in Portland, he debuted a clutch of new songs at a couple of local acoustic shows in 1998, an uncharacteristic move that suggested if there were to be another Pavement album, it would be a Pavement album in name only. Nastanovich later admitted as much: "Pavement music at this stage is Stephen Malkmus," he said in a 1999 interview. "He’s the main songwriter, and the other four guys in the band are trying to make his songs as good as possible.”

But for Malkmus, that process wasn’t happening nearly fast enough. As detailed in Rob Jovanovic’s 2004 Pavement bio, Perfect Sound Forever, Malkmus was growing increasingly tired of the band’s long-distance-relationship status and, once they were finally in the same room together, he’d get frustrated with the time it took to bring everyone up to speed. “I think he realized that we were at one pace, and he was at another pace,” West recounted, “He didn’t really want to have the patience to coax us along in music creativity.” With their time together at a premium, the band opted to focus on Malkmus’ readymade batch of songs, at the expense of developing ideas brought forth by Kannberg (who, despite bringing his power-pop A-game to the band’s most recent releases, would get no spotlight turns on the finished album).

After a by-all-accounts dispiriting attempt to get the album off the ground in Portland, the band decided they needed a professional second opinion. Through their UK label head, Laurence Bell of Domino Records, they learned that another high-profile Brit had joined the Pavement fan club: producer Nigel Godrich, fresh off the consoles for Radiohead’s game-changing OK Computer and Beck’s celebrated space-folk detour Mutations. At the recommendation of the latter, Pavement hired Godrich over the phone without so much as a face-to-face meeting. But once the two parties got down to business, it soon became clear that Pavement’s haphazard work ethic didn’t so easily adapt to the producer’s discipline.

Being a big fan of the band—and recognizing they didn’t exactly have a Radiohead-level budget to work with—Godrich offered Pavement the starving-artist’s special, forgoing his usual fee for future royalties and crashing on friends’ floors to keep expenses in check. But Godrich still had technical standards that were far more elevated than what Pavement were used to working with. After scrapping the band’s initial plan to record at Sonic Youth’s rehearsal room studio in Manhattan, Godrich moved operations to a proper 24-track facility nearby and then over to London’s famed RAK Studios for overdubs.

Where the band previously used the studio as a sandbox, often emerging with a whole extra album’s worth of outtakes, Godrich had them focus on 12 songs, which were whipped into shape through a militaristic, blister-inducing regimen of repeated takes. (Only one, an instrumental freakout dubbed “Shagbag,” didn’t make the final cut.) And with the producer naturally conferring with Malkmus on most creative decisions, other band members started to feel disconnected from the process. (As Nastanovich claims in Perfect Sound Forever, over a week into the sessions, “I went to talk to Nigel and it was pretty clear that he didn’t know what my name was.”) In the end, Pavement were no longer the sort of band that left the mistakes in, even if it meant taking certain members’ contributions out: During the overdub sessions, West’s drum tracks on three songs were re-recorded by High Llamas drummer Dominic Murcott (ironic, since West was initially brought on to be the rhythmic anchor after the 1993 departure of wild-card original drummer Gary Young).

On an album-by-album basis, Pavement tended to alternate between clamor and clarity. Terror Twilight, however, wound up pulling them in both directions at once. Depending on your vantage, it is either the band’s most polished, pop-friendly album or their darkest, most volatile one—laid-back in the classic West-coast Pavement style, yet atypically on edge at the same time. But Terror Twilight is the sort of counterintuitive album where the most melodically intricate songs feel so effortless, yet the slapdash irreverence that once came so naturally to Pavement feels more forced.

The superior tracks further refined the eloquent songwriting Malkmus had introduced on the 1996 stop-gap single “Give It a Day,” where his signature, Velvet Underground-schooled drawl starting to give way to a more byzantine, classically British melodicism. “Spit on a Stranger” and “Ann Don’t Cry” also chipped away at the popular caricature of Malkmus as the aloof, inscrutable slacker, foregrounding the romanticism that’s always been lurking beneath the sardonic surface, where phrases that are difficult to understand allow him to access emotions that are difficult to express. (“My heart is not a wide open thing,” he sings knowingly on the latter track, a rare moment of candor where he fesses up to his aversion to candor.) If Malkmus had sung the line “bring on the major leagues” back in 1994, it would’ve been interpreted as a withering comment on moving up the corporate-rock ladder, but on Terror Twilight’s wistful serenade “Major Leagues,” it sounds like he’s bracing for the familial responsibilities that lay ahead in middle age. Godrich’s trademark atmospheric production finds its most natural fit with these more serene songs, casting them in a moonlit, magic-realist glow and letting the guitars sparkle.

When they weren’t supporting Malkmus’ improved pop craftsmanship, the Pavement of the late ’90s were gradually turning into the world’s wooliest jam band. It’s a side of the band that really came to light on the Brighten the Corners tour, where songs like “Type Slowly” would get substantially stretched out and beefed up. They also frequently test-drove a new track called “And Then” that took the Slint-like mid-sections of songs like “Stop Breathin’” and “Transport Is Arranged” and invested them with a more ominous intensity. “And Then” would find a home deep into Terror Twilight’s second side, where it appeared with new lyrics and a new title, “The Hexx.” The Terror Twilight recording dials back the nasty psychedelic fuzz of the ’97-era live versions for more of a trembling chill, with Malkmus dropping creepy couplets (“Epileptic surgeons with their eyes X-ed out/Attend to the torn up kid/Salivate and reckon with all the sick things that you did”) as if entering a two-sentence horror-story challenge.

“The Hexx” made a convincing case that Pavement’s future lay in weightier guitar workouts. However, the band’s other attempts to flex their rock muscle on Terror Twilight felt a bit like they were puffing out their chests. “Platform Blues” might have made more sense stitched into Wowee Zowee’s unwieldy sprawl, but feels too scattered to fill the role of centerpiece track—its spastic rave-ups (powered by guest harmonica-honkin’ from Radiohead’s Jonny Greenwood) come off like bar-band blooze delivered with air quotes. “Billie” disrupts one of Malkmus’ prettiest verses with an ugly sore-thumb of a chorus. And while “Speak, See, Remember” follows the same loose-intro/motorik-rock-out template as Wowee Zowee highlight “Half a Canyon,” it’s executed with half the focus and intensity. Compared to the unabashedly posh, big-ticket indie rock albums being released by their peers in 1999—like the Flaming Lips’ The Soft Bulletin and Guided by Voices’ Ric Ocasek-tweaked Do the Collapse—Terror Twilight’s willful oddness meant Pavement remained an island unto themselves.

Despite the break-up murmurs, Terror Twilight was received by critics not as an assumed swan song, but a genuine next-level move. The A.V. Club opined that “the time and effort invested in the new Terror Twilight seems to indicate that the group has no intention of throwing in the towel.” And for a while there, that seemed to be the case. Asked about his lack of songwriting contributions on the album, Kannberg told Rolling Stone there just wasn’t enough studio time to hash out his ideas before optimistically speculating he’d “just have more songs for the next record.” In Lance Bangs’ 2002 Pavement documentary Slow Century, we even see the band workshopping a new song during rehearsals for the Terror Twilight tour.

That song, “Discretion Grove,” would soon see the light of day, but not on a Pavement album. It was the lead single from Malkmus’ self-titled 2001 solo debut, the first in a series of consistently enjoyable if far less-hyped albums with his current band, the Jicks (who he’s now fronted for nearly twice as long as Pavement—I guess there is something to be said for living in the same city as your bandmates). That first Malkmus record surfaced 14 months after Pavement played their final shows together in November 1999 at London’s Brixton Academy, at the end of a six-month promotional campaign where Malkmus reportedly turned more insular and unhappy over the course of the tour. Shortly thereafter, Domino announced the band would be “retiring for the foreseeable future”—a somewhat vague communique that further muddied the waters between those who wanted a proper break-up (Malkmus) and those who were anticipating a hiatus (everyone else). Ever since, it’s been hard to listen to Terror Twilight without sensing the 1000-point-font writing on the wall. After a decade of playfully confounding listeners with his elusive wordplay, Malkmus opened “Ann Don’t Cry” with a line so frank and literal, it essentially became Pavement’s epitaph: “The damage has been done/I am not having fun anymore.”

Even now that he’s several years removed from the difficult circumstances that spawned the album, Malkmus’ estimation of Terror Twilight hasn’t exactly improved. Tellingly, it’s the one Pavement album that never received a deluxe 10th-anniversary reissue, a circumstance that can’t help but feel like an implicit judgment of the record. In a 2015 interview with Pitchfork, Malkmus half-jokingly called it “the accidental child of the Pavement catalog,” and in a 2017 Talkhouse podcast interview that detoured into an extended tangent on the album’s recording process, he quipped, “No one really cares about this album that much.” That’s not entirely true, of course: Kannberg holds a much more positive opinion of the record. And there’s evidence to suggest that Terror Twilight’s overtures toward pop accessibility didn’t fall completely on deaf ears—Grammy-winning bluegrass outfit Nickel Creek’s mandolin-tinged cover of “Spit on a Stranger” helped propel their 2002 album, This Side, into the Billboard Top 20.

But if Terror Twilight was by no means a perfect album, it stands today as a perfectly emblematic one—of the band's demise, yes, but also the demise of the very underground/underdog idealism that Pavement represented. In its aesthetic tug-of-war between hi-fi futurism and contrarian weirdness, Terror Twilight portended an indie-rock landscape on the brink a dramatic sea change—a brand new era where Apple commercial syncs and selfie-sticked festival culture dictate that advertising looks and chops are indeed a must. Also, in their own oblique way, the album’s dark undercurrents and convulsive outbursts seemed to be subliminally preparing us for the more unsettled, chaotic world that awaited us on the other side of the new millennium. So maybe Terror Twilight is not merely the flawed, premature final act of an often brilliant band, but more like a savvy act of planned obsolescence from a group smart enough to sense the times were a-changin’, and honest enough to admit that they just weren’t made for them anymore.