Technically, Yo La Tengo existed for almost a decade before Painful. But the Yo La Tengo we know and love begins here, with the record that turns 20 years old tomorrow. It was the first to feature the lineup that continues on today, matching married founding members Ira Kaplan and Georgia Hubley with most excellent third wheel James McNew. It was the first to be produced by Roger Moutenot, who would oversee every subsequent Yo La Tengo album up until this year’s Fade. And it was the first truly great collection of work from a group that would become one of the definitive bands of its genre. As Kaplan explained during a live interview I attended last month at Ohio University — and then demonstrated during a concert later that night — the band still draws heavily from Painful for its live sets, whereas the prior albums have been cast off to obscurity. And that makes sense. Painful was a gigantic step forward, the sound of a budding indie institution coming into its own. “Anyone who ever said they liked our older records more than Painful,” Kaplan said, “I just told them they’re wrong.”

Before Painful, Yo La Tengo’s records were all produced by Gene Holder of the dBs, a pal from the New York and New Jersey music scene Yo La Tengo came up in. Someone at Matador suggested the band try to work with a producer from outside their social circle, which they agreed with to a point. For security, they brought along another friend, Fred Brockman, to co-produce Painful alongside Moutenot. As it turned out, such self-protective measures weren’t necessary. Moutenot had a diverse track record (as Kaplan explained in that interview, “Roger, he had worked with Lou Reed and the Village People”), which suited Yo La Tengo’s penchant for plucking sounds from all over their seasoned record collections. He was willing to go along with stunts like sampling the air conditioner or recording a toilet flush and running it through various processors for “Big Day Coming,” and he helped to craft the reverb-drenched romantic dreamworld that has characterized every Yo La Tengo album since. The chemistry they happened upon here resulted in a fantastic record, but it also laid the groundwork for even greater triumphs down the road. As the Bracys put it in their typically incisive Countdown on YLT, “This is a landmark release that sets the table for a great band’s most impressive achievements.”

How many Yo La Tengo archetypes were crystallized here? “From A Motel 6″ and “Double Dare” are the kind of noise-pop burners that would be refined down the road with “Tom Courtenay” and “Sugarcube,” the sort of songs where Kaplan’s feedback-seared guitar heroics are wrangled into concise structures, their explosiveness harnessed as rocket fuel. He’s allowed to roam free on “I Heard You Looking”; it’s one of Yo La Tengo’s patented guitar pile-ons, a churning web of overdriven chords and solos morphing and crackling against the rhythm section’s steady backbeat. Hubley’s “Nowhere Near” and Kaplan’s “A Worrying Thing” are hushed ballads worthy of 2000’s near-perfect album-length sigh And Then Nothing Turned Itself Inside-Out. “Sudden Organ” nurtures the percussive accessorizing that would become one of YLT’s tricks in a deep, deep bag of them. A wobbling twee cover of the Only Ones’ “The Whole Of The Law” set the stage for plenty of doe-eyed duets and killer covers to come. And with the quiet and loud versions of “Big Day Coming,” we get the dualistic interpretations that would become one of Yo La Tengo’s signature maneuvers.

Perhaps most importantly, Painful affirmed the template of Yo La Tengo album as record-nerd mosaic. There are so many peaks and valleys to be traversed, though you’d never call an album this cool and assured a “thrill ride.” On Painful, Yo La Tengo established that it would be defined by familiar voices and a consistent point of view, not any one style or structure. It’s not as dense or sprawling as some of the masterworks that followed, but it ended up becoming a sort of Constitution that governed one of rock music’s most magnificent discographies. It portended that, yes, a big day was coming for this humble trio from Hoboken — lots of big days, even. That would be reason enough to celebrate Painful even if it wasn’t such a marvelous accomplishment in and of itself.

So: What’s your favorite song on Painful? What memories does it dredge up for you, and are they in fact painful? Where does it stack up among Yo La Tengo’s impressive pile of LPs? Sound off below.