The most important life lesson that a teenage Craig Wedren ever received may have been something that his voice teacher loved to repeat: “Take your bel canto and make it a can-belto!” Wedren, fortunately, was a born belter. A precocious middle-class kid from the Cleveland suburbs, he knew he wanted to be a rock star as soon as he discovered KISS. He sponged up the music his mom played in the car—Elton John, the Doors, Carole King, the Bee Gees—and internalized every lick of it. That knowledge served him well as a young teen: Cover bands were a central feature of middle-school social life in early-’80s Cleveland, and Wedren had both the repertoire and the voice for them.

He honed his falsetto by imitating vocalists like Freddy Mercury, Ozzy Osbourne, and Journey’s Steve Perry—stars who embodied the notoriously high registers of ’70s and ’80s rock radio. Singing into the Shure 58 he’d received for his bar mitzvah, and sharpening his vibrato to cut through the midrange, he learned to make himself heard over his eighth-grade bandmate’s Marshall half stack. They called themselves the Immoral Minority and played at being new wavers—a video shot by Wedren’s childhood friend David Wain, future director of Wet Hot American Summer, captures the 13-year-old singer in all his budding New Romantic splendor—although in Cleveland at the time, there wasn’t really any difference between underground and commercial, cool and uncool. The Bee Gees and the Germs, Def Leppard and Dead Kennedys—they all swirled together in the local teens’ tape decks, their only common denominator the big adolescent feelings they were capable of summoning.

That spirit of openness, combined with his teacher’s technical advice, fatefully shaped young Wedren’s voice and vision, planting the seeds that would yield Shudder to Think, one of the strangest and most distinctive bands ever to emerge from the cauldron of American hardcore punk—creators of the 1994 album Pony Express Record, perhaps the unlikeliest masterpiece of the post-Nevermind major-label alt-rock signing frenzy.

In 1985, when 16-year-old Wedren moved to Washington, D.C. to live with his dad, kids from coast to coast were shaving their heads, shouting choruses, jumping off stages, and figuring out the bare minimum number of chords necessary for a 90-second juggernaut masquerading as a song. A loosely connected network of scenes was coalescing around the nascent American form called hardcore, and the nation’s capital was one of its major hubs, thanks to bands like Minor Threat, the Faith, Void, Government Issue, et al. At the center of the action was Dischord, the staunchly independent, fiercely idealistic record label helmed by Minor Threat’s Ian MacKaye.

Inspired by the example MacKaye and his acolytes set, teenagers assembling at venues like the 9:30 Club and DC Space—not to mention VFW and Grange halls across the region—were realizing that anyone could be in a band; why shouldn’t they? One of those kids was high-schooler Stuart Hill, who taught himself electric bass and cobbled together a group called Stüge. He recruited one bandmate, guitarist Chris Matthews, from Bob’s Famous Ice Cream in Glover Park, where they both worked. (The pipeline from ice-cream scooper to hardcore shredder was a popular career path in ’80s D.C.) Their drummer, Mike Russell, was a university grad with a day job in engineering. When Stüge’s singer left for college, Matthews’ girlfriend suggested that they talk to a new kid from her high school who’d just been kicked out of his band and was desperate to find someone to play with: Craig Wedren.

It was an inauspicious audition. In preparation for the gig, Matthews’ girlfriend had passed Wedren a tape of the band, but Stüge’s approach—Wedren would later describe it as “boom bap boom bap boom bap D.C. hardcore with shouting and vaguely political lyrical content”—couldn’t have been further from his own melodic instincts. “We had Craig come over and we played for him and he totally hated our music,” Hill recalled in a 2015 oral history. But the uneasiness was mutual, he added: “Actually, I didn’t like his vocals at all. He freaked me out when he started singing.” Still, Wedren was bored and lonely, and Stüge apparently didn’t have any better options on the table. “They didn’t like me, I didn’t like them,” recalled Wedren, “but by the end of the rehearsal I was the singer in the band anyways.”

Somehow, something clicked. “There’s just something about putting my vocal style on top of this music that turned it into something else,” Wedren recalled. Constitutionally incapable of shouting out the songs like the band’s old singer, he began finding new ways to attack the lyrics—stranger melodies, odder phrasings, slinkier ways of projecting. In their 1987 demos, you can hear Wedren feeling his way across the contours of the music like a vine seeking purchase on a mottled brick surface: The chugging guitars and double-barreled snare rolls are bog-standard hardcore with a touch of metal thrown in, but instead of barking or screaming, Wedren mercurially pleads, warbles, keens, shrieks, and purrs, theatrical in a way that was unheard of for hardcore frontmen at the time.

Perhaps it was Wedren’s idiosyncratic vocal style that sparked some latent spirit of iconoclasm in his bandmates. As they contemplated their future on a rehearsal commute one day, Russell winced behind the steering wheel: “I shudder to think we’ll be just another boom-bap hardcore band.” For Wedren, it was a eureka moment: They’d been contemplating a name change for their first official gig. Now they had one.

By 1987, the harder-faster-louder ethos of D.C. hardcore had morphed into something more unpredictable, searching, and rhapsodic. Bands like Rites of Spring and Embrace had twisted hardcore’s sturdy steel girders into undulating shapes, eking expressionist forms out of brutalist materials. The nascent Shudder to Think fit loosely into this mold of what was becoming known—with extreme reluctance on the part of the style’s originators—as emotional hardcore, emocore, or simply emo. Their debut 7″, It Was Arson, and LP, Curses, Spells, Voodoo, Mooses—both released in 1988 on Amanda MacKaye and Eli Janney’s Sammich label, a kind of younger sibling to Amanda’s brother Ian’s Dischord—paired hardcore’s muscled churn with yearning bass melodies, lightning-bolt zigs and zags, and Wedren’s garment-rending croon, often multi-tracked and closely harmonized in a way that suggested that all that emotion was too much for the tape to handle.

Shudder to Think joined Dischord proper with 1990’s Ten Spot, an even more ambitiously idiosyncratic showcase of the band’s evolving melodic sensibility and Wedren’s increasingly angelic coo. (Sadly, it was also marred by tinny, two-dimensional production, as though someone had decided to lock all that longing in a lead box.) The band was now officially part of D.C.’s inner circle. But even within a punk scene where individuality was notionally a badge of pride, they felt like misfits.

“People really didn’t like us at first,” Wedren said. “They didn’t get it.” It didn’t help that Shudder to Think were playing opening slots for far more traditional hardcore bands (their first cross-country tour was with Canadian punks SNFU) whose audiences could be knuckleheaded at best. Flying projectiles—bottles, coins, batteries—frequently hurled from the crowd, along with homophobic epithets directed at Wedren, whose style of dressing could be as gender-ambiguous as his voice. (The missiles would continue well into the band’s major-label years; Wedren got hit with a bottle at Lollapalooza 1994, and the meathead crowds when they toured with Foo Fighters could be just as hostile.)

“We were kind of shoehorning ourselves into something we didn’t really fit into,” Hill would later recall. “A lot of people had an expectation with Dischord records, and we just did not fit that mold.”

“At the time, there was this sort of leaden stigma attached to D.C. hardcore,” Wedren said. Especially outside the city, “people’s perception of D.C. hardcore was very narrow and very conservative, and that was difficult for us. We were always trying to shed that and to convince people or prove that we were something else.”

What most set the band apart from its D.C. peers was its apolitical identity. Leftist politics and a communal ethos had become central tenets in the Dischord world. In 1985, a group of D.C. scenesters had staged a “punk percussion protest” at the South African Embassy—the first action in what Fire Party’s Amy Pickering had dubbed Revolution Summer, an attempt to wrest the hardcore scene from the violence and misogyny that was threatening to destroy it, as legions of thrill-seeking male newcomers flooded the pit at shows. That same year, Mark Andersen and Kevin Mattson founded the activist collective Positive Force DC with the intention of redirecting hardcore punk’s creative energies toward social justice and political change. But, aside from Wedren’s tendency to unintentionally draw out the worst in the scene’s most homophobic members, Shudder to Think were largely apolitical. That was especially true of Wedren’s cryptic lyrics.

“That was a straight-up ‘fuck that’ choice on my part,” Wedren told Anti-Matter zine of his lyrical approach in 1995. “Fuck the big messages. Big messages make small music. … I honestly don’t give a fuck about most singers’ opinions about politics. I’m inundated with political information. I don’t need to hear knee-jerk left-wing responses by punk-rock has-beens.”

Wedren’s lyrics were the opposite of knee-jerk—they were head-spinning, running from nonsensical (“The moon bakes all my dough/Who buys it, I don’t know/The bread they make there/Tastes like thin air”) to free-associative (“Cockroaches on the clocks and the cuckoos are all Jewish/I’m naked except for the plaid patch you’re stitching into my groin”) to whatever you’d call the self-indulgent surrealism that closed 1991’s Funeral at the Movies, setting dream-journal spoken-word against the repeated exhortation, “Ride that sexy horse, ride that sexy horse.” While other hardcore singers were focusing their agitprop, Wedren was taking experimental theater courses at NYU, listening to John Coltrane, and reading John Cage, discovering an off-balance world of “delicious discomfort.” (There was also a fair amount of acid involved, he’d later admit.)

By 1992’s Get Your Goat, he and his bandmates were doing everything they could to delight and discomfit in equal measure. The band’s playing on the record is virtuosic, at least by hardcore standards, full of dazzlingly complex time signatures and counterintuitive feints. The songs are colored whirlwinds striking wild poses, like columns of smoke caught beneath strobe lights. Wedren changes forms like a Greek god, shifting on a dime from operatic powerhouse to muttering conspirator to mournful sylph. If Shudder to Think had broken up after 1992, they would likely be remembered today as the authors of one of Dischord’s greatest, most improbable triumphs. But they had bigger things in store.

After three albums for Dischord, they’d lasted longer than most of their peers, and they felt like they were outgrowing D.C. scene politics. Russell and Matthews had both gotten tired of van life and quit the band, replaced by Jawbox drummer Adam Wade and former Swiz bassist Nathan Larson. Wedren and the band didn’t want to be scrappy indie heroes, or big fish in a small, insular pond. “Our aspirations were not to be like Pavement,” he told Pitchfork in 2008; “they were to be like the Cars or Van Halen or Duran Duran.”

There was no time like the early 1990s to try to make that happen; the recent success of Nirvana’s Nevermind had major labels on the prowl for potential crossover jackpots. And Shudder to Think had some powerful fans in their court. One was the Smashing Pumpkins’ James Iha; Shudder opened for the group on a run of dates in 1993. Another was Eddie Vedder, who tipped off Michael Goldstone, the A&R exec who had signed Pearl Jam to Epic. Goldstone knew a thing or two about unconventional, uncompromising alt-rockers, having also signed Rage Against the Machine. He offered Shudder to Think a two-album deal, with the option for up to six more LPs.

Whether you were a day-one fan who’d been following the band since its first releases or a newcomer enticed by Epic’s marketing spend at Tower, the first time you heard Pony Express Record probably came as a cosmic rug-pull. It is bigger and stranger than anything Shudder to Think had yet recorded, by several orders of magnitude. It slips sneakily between known forms and swaggers with cock-rock abandon, an avant-garde behemoth in hair-metal spandex; Gastr del Sol masquerading as Def Leppard, or vice versa—Van Halen getting their rocks off as Slint.

Album opener “Hit Liquor” begins with a rifle-crack snare hit—a favorite trick of Wade’s—before the full band plunges into a loping 12/4 groove, with a dubby undercurrent not a million miles from what MacKaye’s Fugazi were doing in those years. Hill’s bass paces in confused, chromatic circles; the guitars are scabrous and atonal, the vibe nervous, itchy. Wedren begins singing in a deceptively dulcet tone, then almost immediately ratchets up at an odd angle, dangerously close to falling out of key, his vibrato positively seismic. A honeyed falsetto follows, then a plaintive yelp and a basso purr. Within three lines—just 13 meager syllables—he hits four or five different registers. He’s all over the place, prowling, wolflike, almost menacing in his movements.

The song is dripping with sexual portent: “A party of mouths, a finger-fan courtship,” he lilts, with faux innocence; a lasciviously homophonic double entendre lurks inside “liquor.” The lyrics make no literal sense; possible meanings hover over the words like semi-sheer fabric. “Wanna… watch?” taunts Wedren in his gravelliest, most come-hither baritone, and Larson’s guitar explodes into ribbons of liquid distortion. Based purely on the song’s unspoken libidinal energies, Pony Express Record ought to have come slathered in parental advisory stickers. Emo may have developed a reputation for bruised-ego sexlessness, but not Pony Express Record—right from the jump, the album fucks.

Swiz practiced a blunt, unrelenting strain of purist hardcore, but on Pony Express Record, Larson gives free rein to all his rock-god fantasies, unleashing cascade after cascade of squealing harmonics, hammer-ons, pick slides, and incendiary solos. But there’s nothing kitschy or pastiche about the record’s fretwork: He and Wedren contort their fingers around dissonant chords, slash-and-burn soundscapes, changes that make no sense, except by dint of extreme repetition. The contrasts can be laugh-out-loud thrilling—“Gang of $” surgically jabs at a series of ingrown chords, only for “9 Fingers on You” to kick off with a strutting palm-muted stadium-rock riff. Rarely is music this difficult so flat-out fun.

Wade’s drumming is a math-rock fever dream, a patchwork of 17/8 time signatures, 7/4-into-13/8 changeups, trap-door fills, and bridges to nowhere. I’m hardly alone in struggling to parse his timekeeping—yet I’m rarely not toe-tapping to it, if not all-out air-drumming. Without Wade’s rocksteady pulse, the rest of the band would have spun violently out of control, like moons falling out of orbit. Wade’s job, he told Modern Drummer in 2014, was to impose order: “I would find my ‘1’ of the loop. That was the fun thing about these weird riffs—there was no real beginning or ending, so you’d kind of make one…. I’d find the downbeats and accents and the little pockets for the kick drum. My mantra became, ‘The weirder Craig’s going to get with these riffs, the more duh I’m going to play.’” His pulse, accordingly, was a marriage of rocket scientist and caveman. Looking for reliable tentpoles, he turned to classic rock, borrowing patterns from lunkheaded totems like AC/DC’s “Hell’s Bells” and the Stooges’ “Down on the Street.”

Despite the complexity of the music, it’s the opposite of cluttered: Wade leaves vast chasms of empty space for the guitars and vocals to sail through. He makes every fill count, and he obliterates his cues with extreme prejudice. In his targeting, he was assisted by a device that producer Ted Niceley brought to the sessions, called a Russian Dragon—a play on the words, “rushin’, draggin’”—that tracked the timing of his hits by triggering a row of LEDs. “We’d do a take and Ted would watch the machine and go, ‘You’re rushing a bit there, you’re dragging a bit there—do it again,’” he told Modern Drummer. “And maybe if you hit one of the far outside lights it was audible to a normal person. We’re talking milliseconds here. But Ted demanded perfection.” (Ironically, Niceley also produced Jawbox’s For Your Own Special Sweetheart—the year’s other major-label debut by a Dischord defector.)

“We had a lot of unspoken rules for ourselves,” Larson remembered. “You could work in rock riffs, but you had to break it up into parts. Seven of this chord, three of this chord. It was like a broken version of popular music.” Wedren was puzzling out his lyrics on the Amtrak between D.C., where the band was rehearsing, and his home in New York—rehearsal tapes looping on his Walkman, the landscape flashing by as he dreamed up messenger girls riding around on inner tubes, their asses all scraped up; and ape-guy 8x10s; and heaven holding out for high scores. Some of his writing could resemble John Ashbery’s hypnopompic logic in its lateral slide across almost making sense. One song, the prancing “Chakka,” was omitted from the lyric sheet; its free-associative sprawl, Wedren is said to have remarked—“Kiss you can’t vibrate bone/I can get thought of you whe-e-ay-re”—was never meant to scan beyond a purely syllabic level.

If you’ve never heard Pony Express Record, many of Wedren’s lines might look like doggerel, but any fan will recognize them as though they were burned into their brain, branded there with neurosurgical wands. I’ve been listening to the album for 31 years, and a single syllable—picking at random: the saucy way Wedren moans “ooh” in “Earthquakes”—can trigger in me a practically Pavlovian response.

Shudder to Think had their randy moments, but Pony Express Record ventures leaps and bounds beyond their horny early trial balloons, offering the kind of progressive expression of male sexuality that was all too rare in ’90s alternative rock—even in the underground, where ethically minded acts like Fugazi wore the mantle of righteousness, not necessarily pleasure. Shudder to Think offered a glimpse of something else: something liberated and louche, non-traditional, nonbinary, unshackled—unless, of course, handcuffs were your deal, in which case, OK! “It definitely felt like the next step after Get Your Goat, but so much darker,” Wedren said of the album in 2018. “And so much… meaner. And more sexual versus sensual. Get Your Goat is kind of ecstatic and sensual. But Pony Express Record, there’s something kind of midnight black about it. It’s the way the era felt. It was all very nocturnal. Everyone was getting signed to record deals and on tour. There was a lot of heat and a lot of darkness, and I think that trickled into the writing of the record.”

Pony Express Record is steeped in shadow; it’s often as scary as it is sexy. Darkness oozes from the cracks of “Own Me,” a woozy lament (“I’m barely born/Too old for drugs but too young/To know how to not get too high”) that reimagines Lesley Gore’s “You Don’t Own Me” as a blues dirge in the fashion of the Stooges’ “Dirt.” A lone candle seems to illuminate the flickering acoustic introduction to “Trackstar,” a proto-post-rock sprawl influenced by Talk Talk’s Spirit of Eden (itself an album famously recorded in total darkness). After all the rock’n’roll pyrotechnics of the preceding 51 minutes, the album ends with a muffled sob: “I’m drowned/Can’t get far,” mourns Wedren over spiderwebbed acoustic guitars in “Full Body Anchor,” the record’s 110-second finale. “Can’t hear you/Help/Home is where the ground/Can’t come to a well.” The guitar fizzles out like a wick snuffed between licked fingertips.

The album’s centerpiece, arriving smack dab in the middle of the CD, is “X-French Tee Shirt.” The second single, it was also the big hit, at least in relative terms; the video, directed by Pedro Romhanyi—he’d also direct videos for Blur, Suede, Kylie Minogue, and Robbie Williams—fell into rotation in MTV’s Buzz Bin, a promotional gambit deemed to have nearly alchemical powers of turning alt-rock into gold. (“A New Formula: Into the ‘Bin.’ Out Comes a Hit,” marveled a New York Times headline in 1992, noting the successful push given to singles from Temple of the Dog, Alice in Chains, Soundgarden, and Nirvana.)

It’s hard to imagine an unlikelier hit. To begin with, it’s built around one single chord, an eighth-note chug that arcs from end to end like a long, straight road. The only chords that break the monotony, early in the song, sound alarmingly wrong, fistfuls of tritones fished from a wasp’s nest. The song’s introduction thrashes and writhes, torn between the consonance of a gleaming pre-chorus and sudden eruptions of bent and broken metal, shards of rebar thrown down at fucked-up angles. Wedren sings of chewing foil and giving up; you can practically feel the electrical current sizzling through your teeth.

Then, without warning, a hush descends, and over a trim, plucked guitar string, Wedren lights into a lullaby of a chorus, his quavering falsetto barely louder than a whisper: “Hold back the road that goes/So that the others may do/That you let me in just to/Pour me down their mouths.” That’s it; repeat ad infinitum. The lines scroll and tumble, a tangle of weird enjambments and unforeseen pauses, glowing like the bioluminescent mantra of Jeff VanderMeer’s Annihilation.

The melody is a slow-motion roller coaster, a gravity-defying Moebius trip. The chorus loops in 28-beat phrases—the beat regular enough to headbang to, strange enough to buckle your knees. The lyrics float just past the boundary of intelligibility, yet you can feel some kind of meaning trying to break through. “I remember I was thinking vocally about Joni Mitchell—she packs so much challenging and satisfying into her melodic and syllabic flights,” Wedren would later recall. “The lyrics were stream-of-consciousness, but I worked them to a point where the stream was satisfying to me, emotionally and image-wise. So I couldn’t tell you what it’s ‘about’ in the literal sense, but it feels right, and somehow meaningful to me intuitively, like seeing shapes and shadows out of the corner of your eye.”

At some point, you realize that Wedren’s whisper has expanded into a gale-force bellow, hard-panned and all around you. The road that goes just goes and goes, soaring skyward, hammered flat on anvil-sized chords, buoyed by Larson’s screaming harmonics. The fade-out is unambiguous in its implications: This song will never, ever end. It’s still going, way, way out there, like the Voyager spacecraft.

A lot of major-label alt-rock signings didn’t have very happy endings, but all things considered, things could have turned out worse for Shudder to Think. The album sold decently enough—it had moved 60,000 units by 1997. Goldstone, the A&R who signed them, had moved on to Dreamworks by the time they returned to the studio to record a follow-up, 1997’s 50,000 B.C., but he stuck by them, visiting them in the studio to offer his ear, and advice, as a friend.

The album sessions were not without difficulty. In the aftermath of Pony Express Record, by Wedren’s own admission, he went a little crazy—couldn’t sleep at first, then couldn’t stop itching. He was diagnosed with Hodgkin’s lymphoma; he was still in treatment while they were recording 50,000 B.C., in fact. The radiation dried him out terribly, turned his mouth and throat into sandpaper; in between vocal takes, he’d guzzle gallons of water. “I would just go glug glug glug glug, and then sing,” he told Anti-Matter last year. “Glug glug glug glug, and then sing. And then whoever the Pro-Tools engineer was, after we were done recording, would have to go through all my vocal takes and have to remove all the glugs.”

Wedren and Larson’s friendship faltered; each wanted to steer the ship. Where Wedren wanted to take the follow-up in even more extreme directions, the others just wanted to rock. He tried to mollify his bandmates, he says—“write something more soulful, more pop, something that would make Nathan happy and would get the band back in lock step with one another”—but, like so many attempts to save a floundering relationship, it was too little, too late. 50,000 B.C. isn’t a bad album, but it doesn’t have the brilliance of Pony Express Record; it feels like a compromise, like they’re holding back their more esoteric urges—precisely the instincts that made their earlier work so singular.

“I just feel like the point of music is to get sprung,” Wedren said last fall. “To be free of this body, this world, and these rules…. I just want to stay slippery and free.” Shudder to Think’s songs have endured, he theorized, because they’re loose enough, “in this liminal space between meaning and interpretation. I can sing them and have whatever associations I have to the imagery that are relevant to me now, or even revisit where I was and whatever those associations were back then in a more dear and tender way.” He told the interviewer that later that day, he’d be going to rehearsal with his boyhood pal David Wain and some other friends who have a group called Middle Aged Dad Jam Band. They were getting ready for a New Year’s show; at Wain’s urging, he was going to sing some Shudder to Think songs. “Is that going to be strange?” Wedren asked. “No. It’s not going to be strange at all. I love those songs. They’re all very sturdy boats, you know?”

It’s a good metaphor—over the years, those sturdy boats carried Shudder to Think through some choppy waters, and to once unfathomably distant shores. Here’s another one. The one-of-a-kind Pony Express Record is a unicorn, powerful and iridescent and lithe, in shiny black latex. A sexy horse, charging triumphantly into the unknown.