Nineties indie rock was the sound of '80s hardcore kids growing up. And for many get-in-the-van vets, it was a transition that necessitated a clean-slate reboot, whether it was Lou Barlow channeling Dinosaur Jr.’s roar into Sebadoh’s trembling whispers, Jon Spencer reshaping Pussy Galore’s skronk into the Blues Explosion’s funk, or Davids Yow and Sims harnessing Scratch Acid’s strangulated squeals into the Jesus Lizard’s militaristic might. But for Yo La Tengo co-founders/cohabitants Ira Kaplan and Georgia Hubley, the ascent to the Amerindie frontlines was a more gradual, unceremonious process, one that involved downsizing their band from a quartet to a trio, jumping from label to label, and a chronic inability to hold onto a bassist for more than one album at a time. Where they began as a prototypical college-rock outfit in the Velvets-via-Feelies mould (with an unabashed soft spot for '60s-pop covers), Yo La Tengo would go on to define '90s indie—and its evermore sophisticated post-millenial permutations—not by refining their sound, but by blowing it wide open. Painful was the moment of detonation.

The importance of Painful to the Yo La Tengo narrative can be gauged as such: This year marks the band’s 30th anniversary, and they’re celebrating it by reissuing their sixth album, released nearly a decade into their career. Painful marked a couple of significant firsts for Yo La Tengo: it was their first album made with eventual long-time producer Roger Moutenot, and their first to be issued through Matador Records, whose post-Pavement popularity (and resultant Atlantic Records parternship) afforded the band their widest distribution yet. And though Painful was actually the second Yo La Tengo album to feature bassist James McNew, it was the first to fully enmesh his sensibilities with Kaplan and Hubley’s, shirking the typical new-guy/third-wheel dynamic for a more polyamorous professional relationship that continues to this day.

As recently as 1992’s May I Sing With Me (McNew’s debut with the band), Yo La Tengo albums tended to slide back and forth between narcotic noise-pop and hushed folky balladry, producing music that was unerringly charming and consistent if not exactly transcendental. But with the introductory organ hum of the prophetically titled "Big Day Coming", Yo La Tengo’s musical universe instantly turned three-dimensional, projecting a vastness their previous records never really approached; by the time they kick into the dizzying tremoloed groove of the following "From a Motel 6", you can already hear their hearts beating as one. Remarkably, Painful thoroughly expanded Yo La Tengo’s sound by emphasizing two basic ingredients: a little shaker here, and a lot of Ace Tone there (a development so notable, it even earns its own celebratory rock-out in "Sudden Organ"). But taken together, they temper the band’s once-scrappy vigor into hypnotic motorik motions and droning reverberations, while casting Hubley’s plainspoken vocals in a dreamy haze, and inspiring Kaplan to drop the bratty insolence of old for a more congenially conversational drawl.

The cardigan-cozy sound of the record effectively established Yo La Tengo as indie rock’s great romantics. Though musical-cum-matrimonial partnerships weren’t exactly a novelty at the time (see: Kim Gordon and Thurston Moore, Neil Hagerty and Jennifer Herrema, Jon Spencer and Cristina Martinez), Kaplan and Hubley were the rare pair to use their songs to openly address matters of the heart. But while Kaplan and Hubley’s exchanges on Painful can resemble scenes from a marriage, it’s not necessarily their own; rather, a hazy-headed ballad like "Nowhere Near" conveys both an intimacy and non-specificity that make it applicable to any long-distance relationship spent waiting for the phone to ring. And the album’s most tender moment—with Kaplan crooning "baby, I’m in love with you" like a lonesome doo-wop singer abandoned by his crew on some moonlit corner—comes through a to-die-for cover of UK power-popsters the Only Ones’ "The Whole of the Law" (yet another sterling example of Yo La Tengo acting out their record collection). Even Painful’s most blown-out moments are infused with an unspeakable tenderness—Yo La Tengo were no strangers to extended, feedback-screeching jams at this point, but never before had they pulled one off that could actually make you weep ("I Heard You Looking").

What makes Painful so eminently approachable after all these years is that it manages to sound like a fully realized, band-defining statement yet unpretentiously off-the-cuff at the same time. It’s a feeling reinforced by the overflow of material available on this reissue, appropriately retitled Extra Painful on account of its enlarged 2xCD girth (not to mention an additional album’s worth of download-only odds and ends even more revelatory than the bonus disc proper). More so than any other band in recent memory, Yo La Tengo’s body of work hinges on the notion that no song is ever a completely finished, end-state product; what we hear on any given album is seemingly a function of what mood they were in the day it was recorded, what the weather was like on the day of mixing, or how much studio time was left before the budget was blown. There is no such thing as a permanent record; songs have many lives before they’re officially documented and continue to evolve long thereafter.

It’s a concept that Yo La Tengo had hinted at before with the two oppositional treatments of "The Evil That Men Do" on 1989’s President Yo La Tengo and the double, duelling dose of "Upside-Down" on the 1992 EP of the same name. Painful continued the conversation with dramatically different versions of Kaplan’s "Big Day Coming"—the gauzy, weightless opener and the penultimate, fuzzed-out chugger—but Extra Painful ups the ante with three more wildly varying live mutations: a laid-back acoustic take sung by Hubley, a revved-up rendition that’s almost twice as fast as the second Painful one, and a mammoth 19-minute distention that fills in the canyon-like divide between Yo La’s soothing/squalling extremes. Likewise, a percussion- and fuzz-free CBGB performance of "Double Dare" foregrounds the pent-up longing that gets washed over by the original’s shoegazey drive, while an Ace Tone-free demo of the same underscores just how important the organ was in achieving it. And it speaks volumes about Painful’s superior quality—and the band’s surging creative energies at the time—that the steely, Stooges-inspired stomper "Shaker" could be earmarked for a non-album single, while the spectacular slow-dissolve ballad "Slow Learner" would be shelved altogether.

From this point on, Yo La Tengo could no longer be described as mere Velvet Underground wannabes (unless, of course, they were playing them in a movie), and within just a few years, you’d be hard-pressed to even call them a rock band anymore. But then, such a free-ranging future seemed almost predestined when, after a decade of playing the rock'n'roll classicist, Kaplan opened up Painful by declaring, "let’s be undecided." As Yo La Tengo’s post-Painful path would prove, indecision has never sounded so assured.