In order to appreciate what a dirty bomb Heathers was when it was originally released 25 years ago, on March 31, 1989, you have to remember what exactly the “high school movie” was back then. The entire sub-genre was basically worked over in Heathers’ wake, with movies like Mean Girls and Jawbreaker and television shows like Buffy the Vampire Slayer depicting high school as a virtual (sometimes literal) hellscape — jaded, cynical, bitter little pills. But the 1980s began with giggly sex comedies like Porky’s and Fast Times, and then John Hughes took over, imbuing high school narratives with an earnest kindness and “be yourself” messaging. And then here came Heathers, a film whose key image is that of a bomb-toting high school student hoisting his middle finger, and getting it shot off.

Even seen this far on, when its faces have become familiar, its catchphrases iconic, its cynicism marketable, and its synthed-up music time-capsule comical, Heathers still pulses with the visceral thrill of getting away with something — both on- and off-screen. It’s the kind of take-no-prisoners picture that could only have been made by first-timers; it was the first solo effort for producer Denise Di Novi, and the feature debuts of director Michael Lehmann and screenwriter Daniel Waters. Waters was an avowed Stanley Kubrick acolyte, and he was convinced that if he could merely get a copy of his high school black comedy script to Kubrick, the master would agree to direct it immediately. Once he got over that fantasy, he reluctantly turned his 265-page opus over to Lehmann, whose student short film Beaver Gets a Boner (an early exploration of many of Heathers’ themes) had caught the attention of producer Di Novi. Waters’ original script was, according to the director, “bordering on incoherent,” but he saw the greatness inside it, and got to work digging it out.

The script’s most immediate quality was (and remains) Waters’ distinctive dialogue style. He’s said that he created his own slang to keep the dialogue from immediately dating itself — the window between shooting and release is about a year, an eternity in slang time, and with a script written on spec with uncertain timelines, the lag was presumably even longer. So expressions like “It’ll be very” and “What’s your damage?” were ahead of their time, rather than of it. But the writer also had an ear for blunt turns of phrase — like “Fuck me gently with a chainsaw,” “They all want me as a friend or a fuck,” or “Quit pullin’ my dick” — which would pack an extra punch when mouthed by the seemingly squeaky-clean likes of Shannen Doherty or perky, blonde Kim Walker.

That kind of subversion, of teen tropes and ‘80s culture, is all over the screenplay. Casual homophobia was the norm in comedies of the era like Revenge of the Nerds and Adventures in Babysitting, but in Heathers, the homophobia of super-jock characters Kurt and Ram is presented as one more thing to hate about them, and the fine line between gay bashing and gay panic is deftly blurred. (It also gives rise to one of the best running gags, the mineral water, as well as one of the most quoted lines: “I love my dead gay son!”) And the juxtaposition of teen romance devices and the murderous narrative is an endless source of laughs; several moments stick out, but my favorite remains Veronica’s perfectly timed “That’s it, we’re breaking up” after J.D. shoots out the radio.

If a Hughes film like The Breakfast Club is noteworthy for painstakingly finding the shared humanity and multiple dimensions that define characters from all backgrounds, Heathers stands apart for its utter cynicism towards everyone. Director Lehmann frames the teachers up close, almost distorted, like some kind of a David Lynch freak show, and the students aren’t treated much better. This is a world where everyone hates themselves, even queen bee Heather Chandler, who (in one of the film’s most fascinating yet least-discussed moments) stares at her own image in the bathroom mirror at the much-desired college party, and spits at it. Her faked suicide note’s assertion that “I die knowing no one knew the real me” is a kind of cruel joke by its composers, but that claim isn’t far removed from the monocled scrawlings of Veronica’s own journal, where she berates herself for selling out her true friend Betty Finn “for a bunch of Swatch dogs and Diet Cokeheads.”

But that’s par for the course for Veronica, who is carefully positioned as simultaneously an insider and outsider, admitted into the tight circle of popularity, yet framed and edited to reveal her distaste for the entire proposition. That discomfort is established immediately, in the first “caf” scene: she chats with Betty, pushes Heather Chandler to include less popular students in the lunchtime poll, and is reluctant to write the note to Martha “Dumptruck.” And she’s seen wincing at that note’s payoff, not just by the camera, but by J.D.

J.D., whose very initials conjure up the ‘50s shorthand for juvenile delinquent, is given a moniker (Jason Dean) that echoes James Dean, and is outfitted with all the rebel teen trappings: a motorcycle, a black wardrobe, and a devil-may-care attitude. But Waters and Lehmann slyly reveal that it’s all image: he’s no better than his peers, the cool coats and motorcycle provided by his capitalist pig father, who seems to have also passed on a healthy dose of mental instability. J.D. may act cool, but he’s also a monster, and it doesn’t take much work for his crass inhumanity to infect Veronica — who finds herself giggling at Kurt and Ram’s funeral, only to be caught by a teary-eyed little sister (in a shot that recalls her own embarrassment in the cafeteria).

That scene — and the entire movie, really — is a delicate tightrope act by Ryder, who was a mere 16 at the time of production and only pulled the role by, in her estimation, “stalking” the filmmakers after their original first choice, Jennifer Connelly, passed on it. (Had she taken it, we’d have seen a very different trajectory for both of their careers.) Ryder claims her then-agent literally begged her not to take the role, so toxic and potentially career-killing was the script. That agent, needless to say, was subsequently fired. It remains one hell of a performance, the actress somehow pulling off the neat trick of making Veronica both sympathetic and a murderess, often within the same breath.

She came to the film with some previous success; the original trailers billed her as “Winona Ryder, from Beetlejuice.” Christian Slater had a handful of TV appearances and a couple of film roles under his belt, but the role of J.D. (which, according to popular lore, was also pursued by Brad Pitt) made him a star — perhaps less for his own sharp comic timing and good looks than for his decision to perform his dialogue in an unabashed Jack Nicholson impression. (It’s clearest in the later sections of the film, particularly the “NAG NAG NAG” scene, which plays like a Shining outtake.) It’s a stunt performance, but a good one, one where the gimmick works; J.D. could presumably adopt the Nicholson inflections in much the same way he uses the motorcycle, as an affectation, a part of his “character” of the teen rebel. Elsewhere in the cast, future tabloid fave Doherty is something of a revelation in her two-part performance as Heather Duke, initially mousy and then utterly ruthless, while Kim Walker is perfection as Heather Chandler. (In a coincidence too grisly for even this movie, the actress — who mouths the line, “Did you have a brain tumor for breakfast?” — died of brain cancer in 2001 at 32.)

Heathers was released by New World Pictures, the bargain-basement outfit started by Roger Corman, shot in only 32 days on a $2 million budget. As such, the look of the film is occasionally crude, but Lehmann’s direction is stylish, capturing a hazy, dreamlike quality that gives the nightmarish narrative a dash of surrealism. Neither he nor Waters would ever match the success of Heathers; they both found themselves attached to the 1991 Bruce Willis mega-flop Hudson Hawk and never fully recovered. (Lehmann, who mostly works in TV, hasn’t directed a film since 2007’s weak mother/daughter comedy Because I Said So.)

But it almost seems appropriate that these filmmakers came from nowhere, exploded this bomb, and disappeared; even today, Heathers still feels like a movie that was made accidentally, when no one was looking. It goes without saying that it couldn’t be made today — aside from the inherent nihilism, there’s the whole post-Columbine discomfort of a film that ends with a bitter loner trying to blow up a high school (an act that he insists will “infect a generation”). The original ending of Waters’ script was even darker, making Veronica the front-steps suicide bomber, succeeding in killing the entire student body, which is then seen finally crossing clique lines to mingle at a prom in heaven. Nervous New World execs made them rewrite that ending, and the bombing itself is softened considerably by a Looney Tunes-style reveal of Veronica, smoking her cigarette while covered in soot.

Those tiny compromises aside, though, Heathers admirably doesn’t pull its punches (the way its many imitators, most of them smothered by their PG-13 ratings, would). It arrived in theaters just a couple of months after the conclusion of the Reagan administration, which painstakingly framed American life as a perpetual optimistic morning where anything is possible, casually ignoring societal woes and widespread inequality to pine for the kind of grinning 1950s sitcom life sent up by J.D.’s dialogue with his dad. As the decade turned, that daydream was over; popular culture in general and independent film in particular would soon reflect grittier, angrier, and more jaded perspectives. Heathers tanked in its initial release, and that’s not surprising — movies like this always do. But audiences discovered it on video in the months and years after, reveling in its darkness and its “fuck you” cynicism, which would color our vision of high school movies forevermore.