1. Requiem For A Dream (2000)

Darren Aronofsky's brutal adaptation of Hubert Selby's novel depicts the horrors of substance abuse in many forms—heroin, pot, caffeine, prescription pills, hope—with such visceral, breathtaking force that shell-shocked audiences were forced to think long and hard about pouring that first cup of coffee the next day. The result is one of the only genuinely effective, non-hysterical anti-drug movies ever made. Dream flirts extensively with delirious camp during its fever dream of a climax, but retains a pummeling power thanks to Aronofsky's unblinking willingness to trawl deep into the bowels of hell alongside his heartbreakingly fragile characters.

2. Dancer In The Dark (2000)

Starting with 1996's Breaking The Waves, writer-director Lars von Trier all but commandeered the genre of fascinating, beautifully wrought movies that are too agonizing to sit through twice. Waves, Dogville, Dancer In The Dark, and even the less successful Manderlay all center on women making well-meaning but disastrous choices, attempting to help other people but winding up meekly agreeing to their own financial, sexual, and emotional exploitation. And when presented with such humble, cooperative victims, the people around them tend to abandon any semblance of morality and decency in order to take full advantage of the sacrifices they've been offered. Dancer In The Dark follows the same pattern as the others, but it's particularly painful thanks to Björk's sweet, nakedly vulnerable performance as a cringing immigrant factory worker who's gradually going blind while trying to save up money so her son can have the operation that will save him from the same fate. Von Trier calculates his plotlines with exacting, inspired sadism, ensuring that her attempts to reach out to others backfire, her kindness is repaid with betrayal, and every seeming spark of hope exists only to better illuminate the miserable darkness. And yet Dancer is a beautiful film, filled with terrific performances and heartbreaking music, performed by Björk in character.

3. The Passion Of Joan Of Arc (1928)

Von Trier owes his entire painful career to his Danish countryman Carl Dreyer, particularly his silent classic The Passion Of Joan Of Arc, which deals with the ultimate case of a woman suffering for her faith. What makes the film difficult to watch isn't so much Joan's persecution at the hands of her ecclesiastical tormentors, or even Maria Falconetti's famously expressive performance, which registers her anguish in every crevice of her face. Its disturbing intensity comes mainly from Dreyer's refusal to play by the rules: Defying the most basic tenets of cinematic grammar, which require filmmakers to establish spatial relationship on a 180-degree plane, Dreyer instead constructs the film as a series of extreme close-ups, with little sense of where the characters are in relation to one another. That disorientation, combined with the feverish emotions whipped up by the trial, places viewers in a grim psychic space.

4. The Seventh Continent (1989)

Just about every film by Michael Haneke—the fiendishly precise Austrian director of Funny Games, The Piano Teacher, and Caché—could have made this list. An unsparing moralist with a peerless talent for getting under viewers' skins, Haneke backs up his schoolmarm-ish theses on violence with a punishing aesthetic that couldn't be further from the escapist frivolity of Hollywood fare. The first entry in a so-called "glaciation trilogy" that continued with Benny's Video and 71 Fragments Of A Chronology Of Chance, Haneke's brilliant debut feature The Seventh Continent watches with chilling dispassion as an average middle-class family sets about destroying itself. Haneke starts by focusing on the mundane, joylessly repetitive details of their life, then follows the drastic measures they take in carefully dismantling it. In the pantheon of Haneke shocks—the "remote control" in Funny Games, the broken glass in The Piano Teacher, Maurice Bénichou's fate in Caché—Continent's fish-tank scene may be the most emotionally wrenching.

5. Winter Light (1962)

Perhaps the grimmest entry in Ingmar Bergman's "Trilogy Of Faith" (also known as the "God's Silence" trilogy, which should be a good indicator of the bleakness standards at play), Winter Light follows a small group of parishioners who have no celestial answers for their anguish. The opening scenes alone constitute one of the sparest expressions of Bergman's dour spirituality: As a rural pastor performs his noon service, a handful of the faithless faithful go through the requisite motions, but with a palpable disconnection from their meaning. Though he offers himself as counselor, the pastor can't comfort them, because he too is in spiritual crisis; after serving in Spain during the civil war, he witnessed so many bloody atrocities that he struggled to reconcile the idea of just loving God with the reality of human cruelty and violence. In the end, apostasy is the only answer.

6. Bad Lieutenant (1992)

The blunt title turns out to be an understatement: The hard-living detective in Abel Ferrara's Bad Lieutenant, played with fearless brio by Harvey Keitel, surely counts as one of film history's most corrupt cops. He's a gambler and an addict, given to pocketing drug seizures for recreational use and planting them when necessary, participating in sleazy sex-and-drug-fueled bacchanals, and flagrantly abusing the public trust. For his part, Ferrara coughs up some suitably repulsive images: a nun getting gang-raped on the altar; a virtual how-to clinic on preparing and shooting up a ball of heroin; a profanity-laced confrontation with Jesus; and most memorably, a scene in which Keitel pulls over two underage girls and agrees to let them go in exchange for sexual favors. As hard as these scenes are to watch, the clincher may be Keitel's performance itself—a display of raw, unvarnished emotion from a character whose slumbering conscience and faith are suddenly reawakened. Witnessing his transformation is like watching a dried-out junkie.

7. Straw Dogs (1971)

A forceful, unrelenting statement on masculinity and violence, Sam Peckinpah's Straw Dogs sounds like a perfectly watchable home-invasion thriller, concluding as it does with the hero standing his ground and beating back his formidable attackers. But like many of the films on this list, it's a case where the moviemaking is skillful enough to make even its simple revenge scenario seem dangerously potent. Critic Pauline Kael described it as a "fascist classic" for casting Dustin Hoffman as a wimpy, bespectacled academic and pacifist whose manhood remains questionable until he's put through a bloody rite of passage. Hoffman's gruesome showdown with a group of crude locals would be shocking enough on its own, but the infamous scene that prefaces it counts as even more disturbing. Left alone in their home in a seemingly quaint Cornish village, Hoffman's wife (Susan George) is raped by her former lover and his crony. Initially horrified, she eventually responds with something close to ecstasy, underlining her husband's weakness in the context of an indefensible rape fantasy.

8. Audition (1999)

"Kiri-kiri-kiri-kiri-kiri!" ("Deeper, deeper, deeper…") J-horror maestro Takashi Miike has plenty of disturbing images to his credit—a man suspended horizontally by hooks and doused with hot oil in Ichi The Killer, the infamous lactation sex scene in Visitor Q—but Audition, his best film in a walk, unsettles because its shocks are character-oriented, in addition to merely being gross. The first half of the film could be mistaken for austere melodrama, as Miike follows a widowed producer who "auditions" a new wife under false pretenses, and finds a quiet, petite young woman who fits the bill. But the woman turns out to have a dark agenda, and she answers his deceptions in a horrifically extended torture sequence involving a very long needle. Her retribution is Miike's sick idea of social critique, addressing the problem of female objectification with unspeakable (and yet weirdly erotic) acts of cruelty.

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9. Sick: The Life And Death Of Bob Flanagan, Supermasochist (1997)

Simply describing the sadomasochistic stunts pulled by Bob Flanagan, a performance artist who died from cystic fibrosis at age 43, is enough to get half the population wincing as if they were sucking on a lemon wedge. But seeing Flanagan's work in Kirby Dick's surprisingly moving and inspiring documentary Sick is another matter. As a way of combating a body that was constantly betraying him, Flanagan tested his astounding pain threshold in shocking ways, most notoriously including a nail pounded into his penis. (In close-up.) It may sound like something no one would want to watch the first time, let alone twice, but Sick is redeemed by Flanagan's wicked sense of humor and courageous defiance in fighting a disease that normally strikes down the afflicted during childhood.


10. Come And See (1985)

Many films use a child's perspective to tell a war story—it's a easy way to chronicle loss of innocence and portray the consequences of violence. Nothing on film drives this point home quite as effectively as Elem Klimov's Come And See, the chronicle of one boy's struggle to defend his Belarusian village from the Nazis in 1943. Aleksei Kravchenko spends the early part of the film eager to join his comrades, finding a damaged rifle of his own and dressing in oversized military clothing, camouflaging his youth before the war actually takes it from him. Kravchenko's face tells the story, as repeated close-ups document his transformation. By the film's end, it's hard to tell whether dried dirt or actual wrinkles are violating his once-youthful visage. The scene where a Nazi officer gleefully pushes Kravchenko to his knees and points a pistol at his temple to pose for a photograph may once have brought to mind Saigon and that notorious execution of a Viet Cong officer. Now, it's hard not to think of Abu Ghraib.

11. In A Year Of 13 Moons (1978)

There's torment enough in Rainer Werner Fassbinder's deeply personal In A Year Of 13 Moons long before it reaches the sequence that made it semi-notorious. Fassbinder's hero, a transvestite martyr played by Volker Spengler, is a pitiable Frankfurt drifter who had a sex-change operation years earlier, prompted by an offhand comment ("too bad you're not a girl") from an unattainable object of desire. Spengler convinces neither as a man or as a woman, and he winds up subjecting himself to his old crush, now a cruel businessman whose towering office space is accessed by the password "Bergen-Belsen." And on top of it all, the film was shot mere weeks after Fassbinder's lover committed suicide. But 13 Moons saves its most disturbing setpiece for its final act, which contains a monologue on self-mutilation set against footage of the killing floor in a slaughterhouse. Fassbinder super-fan Richard Linklater lifted the idea for Fast Food Nation as a tactic for letting audiences know where their steaks and burgers come from, but the combination of those images and the dissociated voiceover makes 13 Moons considerably more disturbing.


12. Safe (1995)

A sort-of horror movie in which the monster is the entire world, Todd Haynes' Safe follows a rich, empty housewife (played masterfully by Julianne Moore) into the depths of "environmental illness"—a malady that real-world doctors still can't agree on. Is it all in her head, which is half-vacant and in need of something to worry about when all basic needs are met? Or is she just sensitive to low levels of toxic chemicals that most people simply don't notice? The film doesn't offer an clear answer—instead, it follows Moore through incredibly uncomfortable anxieties and unpeggable illnesses. She ends up at a wellness retreat, which at first seems to offer some hope, but she's soon sucked even deeper into the discomfort of her own mind. It's pure bleakness.

13. Irreversible (2002)

Gaspar Noé's Irreversible picked up some well-deserved notoriety for its centerpiece, a gasp-inducing nine-minute single-take sequence in which Jo Prestia anally violates Monica Bellucci at knifepoint in a grimy (and highly symbolic) red underground tunnel, then beats her to an unrecognizable pulp. There's nothing cinematic or subversively sexy about the rape scene; it's a ghastly, raw experience that seems to go on for hours, with Bellucci's muffled cries and wide, blank eyes becoming increasingly inhuman as the process drags on. But Noé doesn't make the rest of the film any easier to take. Laying out the story in reverse chronological order, he begins with a stomach-churning act of revenge for the rape, then sets his camera spinning slowly end-over-end, preventing viewers from gathering their bearings and turning the film into a ghastly carnival ride. Throughout the film, his shocking content and his startling intimacy with his characters make for a strikingly vivid, immersive, intense experience, but it's a singularly exhausting one as well.

14. Boys Don't Cry (1999)

Graphic rape scenes are tough enough to sit through without squirming, but the brutal assaults in Boys Don't Cry make repeat viewings of the film an act of psychic self-abuse. Based on the real-life tragedy of transgender 21-year-old Brandon Teena—played with haunting depth by Hilary Swank—Boys is relentless in its portrayal of barbaric bigotry in small-town Nebraska. After Swank starts a romantic relationship with Chloë Sevigny's Lana Tisdel, Lana's redneck friends forcibly expose Teena as a biological female, then savagely rape her before the hatred escalates to an inevitably horrific end. Just as sickening as the violence, though, is the complicity of Lana's mother—who calls Teena "it" and ultimately gives the boys sanction to "clean up" the situation—and the outright antagonism (bordering on titillation) of the hick sheriff who grills Teena after the rape. The fact that the film's events are based on truth—and the lingering attachment Boys Don't Cry has to the hate-fueled murder of Matthew Shepherd around the time of its release—only magnifies its gut-crawling impact.

15. Grave Of The Fireflies (1988)

From the opening scene showing 14-year-old protagonist Seita dying on a train-station floor as harried travelers look on bemusedly, it's clear that Grave Of The Fireflies isn't going to be easy to watch. An animated Japanese film as visually beautiful as it is emotionally draining, Fireflies finds tragedy in the horrors of war and the dangers of human pride. The story of two Japanese siblings orphaned during the firebombing of their village during World War II, Grave draws out the suffering of Seita and his younger sister Setsuko over 88 quietly horrifying minutes as they struggle, and eventually fail, to survive in a bleak, war-torn landscape. In spite of its dark subject matter, Fireflies is brightly colored and peppered with sweetly innocent moments between brother and sister, making their eventual fates all the more disturbing.

16. When The Wind Blows (1986)

This deceptively sweet little British animated feature emphasizes the cost of war on a very personal level, by observing a quiet rural couple preparing for impending nuclear conflict, then slowly dying of radiation poisoning afterward. Naïvely accepting everything their government pamphlets tell them (though they don't understand much of what they're told, and remain sure that since they can't see or feel any radiation, it can't possibly be hurting them), they fumble through their days, gently squabbling and supporting each other in homey old-married fashion without comprehending either the scope or the causes of the fight that's killing them from afar. Perhaps the saddest part is their conviction that nuclear war will be no different from World War II, which they lived through, and that if they just tough it out and tighten their belts, they can get through lethal radiation poisoning the way they got through wartime shortages. Much like Grave Of The Fireflies, When The Wind Blows is adorable in its personal, knowing details, and excruciating in its big picture.

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17. Leaving Las Vegas (1996)

It's been a long fall for Nicolas Cage, from celebrated Best Actor Oscar winner a mere decade ago to the star of Next, Ghost Rider, and (tee-hee, "How'd it get burned?") The Wicker Man. It's honestly hard to remember at this point what a revelation he was in his Oscar-winning role in Leaving Las Vegas, as a failed screenwriter pointedly setting out to drink himself to death. The film, written and directed by Stormy Monday's Mike Figgis, is more consciously polished and Hollywood-y than most of the films on this list, but it has much the same quality of unstintingly, aggressively delving into just how miserable human beings can get. It isn't enough, for instance, that co-star Elisabeth Shue is trapped in a degrading life as a Vegas prostitute. It isn't enough that her best friend is an abusive, suicidal drunk who seems content to drag her down with him. It isn't enough when she gets gang-raped, and subsequently evicted from her home by landlords clearly uncomfortable with the disreputable appearance of a bruised-up, limping rape victim. No, she actually has to get mocked and abused on her way home after the rape, as her taxi driver, noticing how gingerly she's moving, asks if she got "a back-door delivery you weren't expecting," then tells her she was asking for it by dressing the way she does. Only Figgis' glittery, somber direction and the leads' stellar performances turn this wallow in miserablism into something sadly poetic.

18. Jonestown: The Life And Death Of Peoples Temple (2006)

19. S-21: The Khmer Rouge Killing Machine (2003)

Though they take drastically different approaches, the Jim Jones documentary Jonestown and S21 are both far too intense and draining for repeat viewing. S21 coldly but powerfully appraises the devastating aftereffects of totalitarianism through the firsthand stories of survivors of Khmer Rouge terror. Jonestown, meanwhile, traces the tragic rise and fall of Jim Jones, a fiery idealist and social activist corrupted by power. People's Temple attains an almost unbearable intensity in a heart-stopping climax that draws extensively on audio footage miraculously documenting Jones' endgame strategy of poisoned Kool-Aid and mass suicide. It's as close to being there as humanly possible.

20. The Last House On The Left (1972)

Taxi Driver is considered the definitive rebuke of '70s vigilante movies, but it's a laugh-a-minute joy ride next to the vengeful depravity depicted in The Last House On The Left. Drawing from Ingmar Bergman's The Virgin Spring, Wes Craven's brilliantly unwatchable first feature is a no-holds-barred depiction of the rape and murder of two teenage girls by a pack of hippie lunatics, and the graphic revenge the girls' parents enact on the murderers. Last House looks cheap and amateurish, which adds to its snuff-film-style realism. Never has the gulf between "great film" and "enjoyable" been so wide.

21. Million Dollar Baby (2004)

The first three-quarters of Million Dollar Baby play like an old-fashioned sports movie, focusing on the heartwarming father-daughter dynamic between coach Clint Eastwood and boxer Hilary Swank. Then (spoiler alert!) Swank suffers a horrible accident in the ring, and Million Dollar Baby is suddenly rich with ripped-from-the-headlines relevance as Eastwood wrestles with the question of whether he should euthanize his surrogate daughter. The decision is appropriately gut-wrenching, and Eastwood's direction is always tasteful, but who wants to ponder the difficulty of putting a loved one out of their misery if fate doesn't require it?

22. United 93 (2006)

Writer-director Paul Greengrass dramatizes the events of September 11 on the ground and in the air with a "you are there" veracity that's gut-wrenching and surprisingly probative. From the initial confusion to the panicked response, United 93 explains what the whole last six years have been like, from shock to violence to exhaustion. But Greengrass' refusal to insert any kind of distancing effects means that viewers get to relive every second of sick horror from one of the worst days any of us will ever experience. A lot of Americans didn't want to see United 93 even once, and it was hard to blame them.

23. Lilya 4-Ever (2002)

Just prior to Lilya 4-Ever, Swedish writer-director Lukas Moodysson made Together, a movie so generous in spirit that a lot of its fans found this follow-up, a comparatively bleak story of a teenage Russian sex slave, too tough to take. Actually, Lilya follows logically from Together as another profound illustration of how people need people. (A little familial support would've prevented most of the movie's string of tragedies.) But in spite of a spectacular lead performance by Oksana Akinshina—and a lyrical final scene that tries to put a happy spin on human misery—Lilya 4-Ever essentially asks its audience to watch the hopes of a bright, pretty girl get crushed one by one. It's powerful stuff that lingers in the memory so strongly that a second viewing may not even be necessary.

24. Nil By Mouth (1997)

Gary Oldman has openly said that he appears in dreck like Air Force One because Hollywood paychecks let him fund his own indie films. So far, though, his only writing-directing project is Nil By Mouth, a gritty, grueling drama in Mike Leigh mode. Like Irreversible, it centers on a protracted, nauseating act of violence against a woman, framed within a nervy, talky plot. But Nil By Mouth is less story-driven; it mostly captures, intimately and unsparingly, the details of working-class life in South London, among addicts and alcoholics. It's an impressively immediate, immersive film, but a hard one to sit through, thanks to its direct look at physical and emotional abuse. Then again, the accents are so dense, and the dialogue flies so fast and furious, that it may be necessary to watch it twice just to follow what's going on. Sometimes even the most exhausting films have to be watched more than once.