In the early months of 1990, it seemed like a serial killer, a restaurant with unusual menu items, and a toy scuba diver might change the face of movies for good—the boundaries of what movies could and could not do were on the verge of collapsing. A series of controversial films forced a conversation about what was permissible, as well as a reexamination of a ratings system that had been in place for the past 22 years. On one side: the MPAA, whose ratings board worked in secret and drew no distinction between films that didn’t meet the guidelines for an R rating and smut, lumping artistic but explicit filmmaking into the category of pornography. On the other: those trying to carve out a space for films aimed squarely at adults without the stain of the X rating. And for a while, it looked like one side would prevail thanks to some too-extreme-for-younger-viewers films that forced the MPAA to reconsider its system. Those in favor of freedom of expression capped a decade in the trenches of the culture wars with a victory. But that didn’t last.

The 1980s saw one heated cultural debate follow another, the results of cultural divisions that had deepened since the 1960s and helped give rise to a religious right eager to protest whatever they felt to be an affront to their values. They didn’t lack targets and, in fairness, those targets felt closer at hand thanks to neighborhood video stores with curtained “adults only” sections and scandalous music videos just a click away on cable. Music became one high-profile battleground thanks to Senate hearings spurred by the Parents Music Resource Center, but movies became another front. Though ultimately more talked about than seen, Jean-Luc Godard’s 1985 film Hail Mary—featuring a modern day retelling of the nativity story—earned protests and the condemnation of Pope John Paul II. But that was a mere prelude to what greeted Martin Scorsese’s The Last Temptation of Christ in 1988.

More often, however, the MPAA ratings system served as the barometer for what the culture at large could tolerate and what needed to be placed out of reach. An X rating meant many theaters wouldn’t play a film and many TV stations and newspapers wouldn’t accept advertising for it, but an R-rated film could play anywhere and, thanks to generally lax enforcement of age restrictions, be seen by virtually anyone (if not in theaters, then not long after on home video or cable). This most often affected horror films, some of which opted for self-policing warnings rather than ratings. The ads for George Romero’s 1985 film Day of the Dead, for instance, featured the warning: “Due to scenes of violence which may be considered shocking, no one under 17 admitted.” The Texas Chainsaw Massacre 2 chose a similar approach the following year after multiple failed attempts to make the edits needed to earn an R. But this approach had problems of its own: Films without an MPAA rating had some of the same trouble placing ads and finding theaters as X-rated films; in practical terms, they were essentially X-rated, except in name.

Many more filmmakers, though, kept cutting and cutting until their work fit within the MPAA’s parameters of an R. Sometimes that process turned into contentious clashes that spilled out into the press. And sometimes the controversy doubled as publicity, as with Alan Parker’s 1987 film Angel Heart, which drew extensive prerelease press thanks to the MPAA’s objection to a graphic sex scene featuring Mickey Rourke and Lisa Bonet. The controversy ultimately didn’t help the film commercially. But maybe a better managed controversy could. In his 2004 book Down and Dirty Pictures, Peter Biskind draws a direct line between the unintended scandal around Angel Heart and Miramax’s planned run-in with the MPAA with the 1989 film Scandal. Harvey Weinstein pushed British producers Steve Woolley and Nik Powell to deliver an X-rated film, then made the most of the ensuing controversy. (In February 2020, Weinstein was convicted on charges for first-degree criminal sexual act and third-degree rape.) Ultimately, the scandal around Scandal would look like table-setting for the events of 1990, a year when a handful of films threatened to foment a full-scale revolt that would carve out a space for films that fell outside the vague but impermeable boundaries of the R rating.

The rumblings started the previous fall thanks in large part to a low-budget film made years earlier. John McNaughton’s Henry: Portrait of a Serial Killer was shot in Chicago in 1985 and 1986, and had mostly sat on the shelf ever since. A no-frills, analytical depiction of a serial killer in action starring a then-unknown Michael Rooker, Henry had picked up a reputation as a great but unreleasable film, its potential distributors scared off by the inevitable X rating. In the fall of 1989, however, its reputation started to prove too strong to deny, particularly after a successful screening—at the invitation of Errol Morris—at the Telluride Film Festival, where McNaughton publicly fretted it might be “too arty for the blood crowd and too bloody for the art crowd.”

McNaughton also talked to Chicago Sun-Times critic Roger Ebert about his struggles with the MPAA, who’d “told McNaughton his film’s very tone was X-rated, and that it could not suggest specific cuts that would win an R rating.” In January 1990, however, Henry started a limited run with no rating at all, becoming a cause célèbre as it made the rounds. Ebert and Chicago Tribune critic Gene Siskel took up the fight on an April episode of their TV series Siskel & Ebert. “We’re absolutely the only country on earth that doesn’t believe there’s such a thing as an adults-only movie, a movie that is unsuitable for people under 17,” Ebert argued, then taking the opportunity to revive a proposal for an “A rating,” a category for movies that fell between the R and the X and featured material for and only for grown-ups.

By the time the episode aired, there were even more examples to call upon as the MPAA brush-ups continued. Some had predictable outcomes: Unlike Cannon Films, the distributors of The Texas Chainsaw Massacre 2, New Line cut several minutes from Leatherface: The Texas Chainsaw Massacre III to secure an R. Others proved more contentious: Reviewed in the same Siskel & Ebert episode as Henry, Peter Greenaway’s The Cook, the Thief, His Wife & Her Lover became an art house hit despite being released without an MPAA rating. Arguably, it became a hit because of that rating.

Greenaway is a maker of dense, formally complex films often filled with graphic sex and violence, and he was an unlikely director to break through to the mainstream. An allegory for the destructive politics of the Thatcher Era arranged in compositions inspired by a Flemish painting, The Cook, the Thief, His Wife & Her Lover demands of viewers both patience and a strong stomach, opening with a man being forcibly covered in dog excrement then launching into the first of many long, unbroken horizontal journeys through the busy French restaurant that serves as its primary setting. (You could make a drinking game out of the film’s close-ups and come away unable to operate heavy machinery.)

Greenaway is always divisive—the film split critics and prompted walkouts at TIFF the previous fall—and this is the sort of movie that might struggle to draw crowds without controversy. And, again, the controversy wasn’t entirely accidental. Miramax purchased the film and, in a rare instance of Weinstein digging in to protect a director’s vision, refused to cut it to earn an R rating. (It’s darkly ironic that Michael Gambon’s character, the thief of the title, resembles Weinstein: an abuser of women and a bellowing vulgarian who fancies himself a man of refined taste.) The promise of sex and violence beyond the R rating helped draw crowds, as the movie earned more than $7.5 million in North America. But more importantly, it also provided fodder for the argument against the X rating. The Cook, the Thief is undeniably too extreme to fit under the R-rated banner—costars Helen Mirren and Alan Howard spend a good portion of the film’s second half completely nude, and the film’s infamous climax is stomach-churning in ways Leatherface could only dream of being—but it was also an unmistakable work of art worthy of a grown-up audience, one that couldn’t be altered without changing its essence. Its very existence highlighted a flaw in a ratings system incapable of categorizing it.

It didn’t take long for Miramax to clash with the MPAA again, this time over Tie Me Up! Tie Me Down!, Pedro Almodóvar’s follow-up to his breakout hit Women on the Verge of a Nervous Breakdown. A provocation, the film makes a love story of a deranged fan (Antonio Banderas) imprisoning a film star (Victoria Abril) who’s become an object of obsession. But the MPAA seemed to object not to its themes but its content, particularly a noisy sex scene and a memorable shot of a bathtub toy. Released without a rating on May 4, it went on to earn more than $4 million at the North American box office.

But should it have earned more? And could Henry: Portrait of a Serial Killer also have found a wider audience? Their distributors attempted to find out in court. On May 14, Henry’s Maljack Productions filed suit against the MPAA in federal court, arguing that the promise of an X rating had impeded its commercial potential. Nine days later, Miramax did the same in the New York Supreme Court on behalf of Almodóvar’s film. And though Miramax lost the latter case, it would prove instrumental in changing the ratings system—if not necessarily for the better.

Judge Charles Ramos argued that Miramax had failed to show that “the X rating afforded Tie Me Up! was without a rational basis or arbitrary and capricious,” going on to suggest that “this proceeding may be just publicity.” But he also said that “the manner in which the MPAA rates all films, not just Tie Me Up! Tie Me Down!, causes this Court to question the integrity of the present rating system” and that “the rating system censors serious films by the force of economic pressure.”

MPAA president Jack Valenti thought otherwise. He implemented the rating system in 1968, shortly after assuming control of the organization, which he would continue to head until 2004. He’d changed the system only once, introducing the PG-13 rating in 1984 after controversies greeted the graphic content of the PG-rated Gremlins and Indiana Jones and the Temple of Doom. But the cumulative effect of the controversy around the X rating made some kind of adjustment seem unavoidable.

Call for change mounted over the summer: In a full-page editorial published in the Los Angeles Times on June 17, critic Charles Champlin joined Siskel, Ebert, and others in arguing for an end to the X rating. But he inadvertently pointed to another problem. When suggesting that a new rating could be applied to “tough films of undeniable artistic intent,” he argued that the rating system should remain quantitative, not qualitative. In other words, that there shouldn’t be a separate rating for tough films without artistic merit and that in fact, it wasn’t the MPAA’s job to define artistic merit. So what would take its place? Per Champlin, the problem came from the X itself and the implications it had picked up by its pornographic associations. Replace the X and you solve the problem.

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As this debate raged on, Life Is Cheap … but Toilet Paper Is Expensive started a smaller dustup. Wayne Wang’s now largely forgotten film follows an unnamed American man (Spencer Nakasako) to Hong Kong on a mission to deliver a suitcase to a local crime boss. The fragmented movie features a memorably endless on-foot chase scene through the streets of Hong Kong but also: footage of a man defecating; long, bloody, all-too-real scenes of ducks being killed for restaurant use; and a glimpse inside a pregnancy fetish magazine called Poppin’ Mamas. Given an X rating, its distributor instead opted to self-apply a rating of “A” (for “adults only”) for its release. The already released horror comedy Frankenhooker then began using the same rating. A movement was beginning—if the MPAA wouldn’t create an A rating, it seemed filmmakers would have to create it for them, and thus carve out a space safe for adult material of non-pornographic nature (the occasional appearance of Poppin’ Mamas aside).

But the MPAA chose another option, one that echoed Champlin’s suggestion. On September 26, it dropped the X rating and replaced it with a new denomination: the NC-17 rating. “We are going back to the original intent of the ratings system,” Valenti announced. “It takes us back to the days, hopefully, of Midnight Cowboy, Last Tango in Paris, and A Clockwork Orange,” he continued, noting three of the small handful of non-pornographic films to be released with an X rating. At first it seemed to work. The first NC-17 film, Philip Kaufman’s Henry & June, was released to a handful of theaters in October, then eventually expanded to mainstream theaters and placed ads in newspapers and on television. It performed respectably at the box office.

But who wants to merely perform respectably? The promise of the NC-17 rating faded not long after its introduction. While NC-17 might have sounded more respectable, it still limited a film’s audience and cut into its post-theatrical life. A true, enforced adults-only rating cut off all the under-18 viewers who could take advantage of theaters turning a blind eye to those buying tickets to R-rated movies, and it didn’t solve the problem of Blockbuster Video, which still refused to carry any movies above an R rating. (To please Blockbuster, Miramax cut almost 30 minutes from The Cook, the Thief to create an R-rated version.) The list of films from the early days that kept the rating is short and mostly includes titles like the Andrew Dice Clay stand-up movie Dice Rules. The list of films reedited to earn an R is much longer.

Two 1992 films capture the divide: Abel Ferrara’s Bad Lieutenant played the art houses it would play anyway with an NC-17 rating; Paul Verhoeven’s Basic Instinct played widely after making just enough cuts to somehow squeak by with an R. Domestically, the former made $2 million; the latter made $117 million (and even more internationally). By the decade’s end, the promise of a new era of films filled with mature content went unfulfilled, despite the occasional outlier like David Cronenberg’s Crash; more tellingly, the NC-17-rated Showgirls had to wait until home video to pick up its cult following. Those types of movies were allowed to shed the unwarranted connection to porn, but still carried a stigma of being “worse than R;” any sense of actual change was nonexistent, aside from the swapping of a couple of letters and numbers.

In the summer of 1999, inspired by the digital censoring of nude bodies added to Stanley Kubrick’s Eyes Wide Shut to dodge an NC-17 rating (and similar clashes around Summer of Sam, Casino, and Natural Born Killers), Ebert published an impassioned editorial. Its subject: the need for an A rating. It felt like 1989 all over again. And 30 years after a brief, loud attempt to overturn the system by way of scenes of cannibalistic cuisine and impassioned moans, it still does.

Keith Phipps is a writer and editor specializing in film and TV. Formerly: Uproxx, The Dissolve, and The A.V. Club.