What, you may ask, is the difference between a feel-bad movie and a tearjerker? Basically: Crying at a tearjerker brings catharsis, relief, even a sense of joy. A feel-bad movie, though, is a good movie that feels just awful to sit through, the kind of gripping story you might never be able to bring yourself to watch again. It is, in short, the very opposite of a feel-good movie. But if you find yourself intentionally seeking a film that puts you in a deep state of despair, who are we to judge?

Below, we recommend 22 tough sits that will do just that—though we decided not to include films about the Holocaust, slavery, and other historic atrocities, since it’d be easy to fill a list like this with only those sorts of stories. (There’s also no torture porn and few all-out horror movies as well: Graphic violence isn’t exactly the bad vibe we were going for, as you’ll see.) Press play, if you dare.

A Clockwork Orange (1971)

Stanley Kubrick’s incredibly influential dystopian classic was widely censored upon its release, and watching it today, you can understand why—there’s an attempted gang rape within the film’s first five minutes, and things only get more disturbing from there. But even beyond the various acts of “ultraviolence” perpetrated by Alex DeLarge (Malcolm McDowell) and his (sometimes) loyal “droogs”—not to mention the viscerally uncomfortable sequence in which Alex is “rehabilitated” using aversion therapy, and eye-opening clamps that reportedly blinded McDowell temporarily—Clockwork is a symphony of stylish negative energy. It’s telling that Anthony Burgess’s original novel includes a final chapter in which Alex reforms for real…but that coda is nowhere to be found in Kubrick’s film. —Hillary Busis

Taxi Driver (1976)

There are even more Travis Bickles in the world now than there were when Taxi Driver first shocked audiences, which might make this early Martin Scorsese masterpiece even more depressing these days than it was then. But Taxi Driver holds up for far more reasons than disheartening topicality, from Robert De Niro’s era-defining performance to Scorsese and Paul Schrader’s cynical approach to politics and the media. New York has changed a lot since Taxi Driver, but the bitter aura of its ’70s nadir isn’t hard to relate to at all. —Katey Rich

The Chocolate War (1988)

We love to romanticize rebellion, but the truth is much harder to bear. Usually, those who stand up to resist cruelty, unfairness, and indifference do so alone. And usually, they’re also destroyed for it. Ilan Mitchell-Smith stars as a teenage boy at a hard-knocks Catholic high school who decides to make a stand nonetheless. Based on Robert Cormier’s celebrated YA book, the film follows Mitchell-Smith’s character as he steadfastly refuses to take part in the annual chocolate-selling contest that raises a fortune for Trinity High School. His refusal cannot be allowed, lest it inspire others, so he is marked for annihilation. The bullying and torment he experiences—from fellow students, as well as the corrosive teaching staff—nearly succeeds (John Glover is especially charismatic as the sadistic Brother Leon.) But the boy doesn’t break, which is something worth celebrating. Director Keith Gordon (also cited on this list for his follow-up movie, A Midnight Clear) ends the film with one of the key bullies being knocked from his perch. But the happy ending is dashed when we see what takes that boy’s place: something far, far worse. — Anthony Breznican

The Vanishing (1988)

This is going to sound like hyperbole, but the Dutch version of The Vanishing is even more upsetting than the fact that Hollywood later convinced director George Sluizer to make an English-language version with Sandra Bullock, Kiefer Sutherland, and a happy fucking ending. Here’s the plot of the original, minus the stunning final scene, which you should see for yourself so it can haunt you forever: A young couple named Rex and Saskia stop for gas at a rest area during a road trip. Saskia vanishes without a trace. (The Dutch title is Spoorloos—how great a word is that?) Rex spends years trying to solve the mystery of what became of her, and even goes on TV to tell whoever abducted his girlfriend that he just wants to know what happened. The psycho in question offers Rex a horrific deal: He will reveal all to Rex by doing the same thing to him. Is he in or out? The grim, unforgettable plotting of original movies lies in its simplicity, as well as how it hurtles toward a last scene that constitutes a lot of people’s worst nightmare. The movie’s a stunner in both senses of the word. —Jeff Giles

A Midnight Clear (1992)

Near the end of World War II, a group of US Army reconnaissance soldiers (Ethan Hawke, Arye Gross, Kevin Dillon, Frank Whaley) take up residence in a bombed-out villa near the front lines just as Christmas is approaching. While trying to gauge the presence of enemy tropes, they encounter a group of German soldiers who say they don’t believe in Hitler’s war and don’t want to die for it but know their families will be held responsible if they surrender. The groups devise an ingenious plan to stage a fake battle that will allow the Germans to be captured with honor, while giving credit to a shell-shocked member of the American scouts (played by Gary Sinise) who can then be sent home a hero. Director Keith Gordon unsparingly adapts William Wharton’s novel, which steers this hopeful premise into the darkest imaginable abyss. It’s a great movie, a great Christmas movie, but one that will break your heart and leave it that way. — A.B.

Seven (1995)

What David Fincher gets away with at the end of Seven might not be quite as audacious as you remember—we don’t actually see what’s in the box—but it’s still one hell of a slap in the face, particularly for 1995 and for a filmmaker whose only previous feature credit was the disastrous Alien 3. Like so many Fincher films that would come, including the one that billed itself as the feel-bad movie of Christmas 2011, the style swoops the audience along through the many awful things encountered by the cops played by Brad Pitt and Morgan Freeman. You might even find yourself wanting to watch it again despite the pit in your stomach by the end. –K.R.

Funny Games (1997)

Is it a pitch-black comedy of manners, a stinging satire of both bourgeois values and our violence-obsessed culture, a nasty bit of nihilism dressed up as art, an all-too-believable domestic horror story, a postmodern experiment? Michael Haneke’s ironically titled thriller intentionally resists categorization. But one thing about this Cannes standout is clear: After sitting through the sadistic games that a pair of extremely polite interlopers put an upper-class Austrian family through, you absolutely do not need to watch Haneke’s 2007 English-language remake, which is basically the same movie but starring Naomi Watts and Michael Pitt. Unless you too are a glutton for punishment. —H.B.

Happiness (1998)

The ’90s independent scene was filled with grim, rather joyless portraits of American suburbia, but none took on domestic middle-class misery as frankly and relentlessly as Todd Solondz’s Happiness. Centered on the unpleasant lives of three adult sisters, the film opens with the reveal that one of the women, Trish (Cynthia Stevenson), is married to a well-regarded psychiatrist (Dylan Baker) living a secret life as a pedophile. Things somehow get darker from there, with the film frankly depicting grooming, sexual assault, and other forms of abuse. The chilling effectiveness of the film rests in its unsentimental ordinariness—its starkly convincing portrait of depraved, monstrous behavior occurring right next door, just beyond a well-manicured lawn. —David Canfield

A Simple Plan (1998)

“You’ve got to remember how people see you. You’re just a normal guy. A nice, sweet, normal guy…. Nobody would ever believe that you’d be capable of doing what you’ve done.” These brutally cutting words are meant as comfort to Bill Paxton, who has unleashed a torrent of pain, suffering, and death after finding a bag full of millions of dollars in the woods. As his Lady Macbeth of a wife, Bridget Fonda reassures him that he is very likely to get away with all his terrible deeds, if only he keeps going. But this is the gut punch of Sam Raimi’s film, based on the book by Scott B. Smith: Paxton’s character was a good man, at least until he discovered his own ruthlessness in that bag of cash. When he had nothing, at least he had his soul. With that gone, there is little comfort in her promise. No one who knows him could imagine he might do such things, which means no one really knew him. Including himself. — A.B.

Requiem for a Dream (2000)

Where to begin with Darren Aronofsky’s addiction opus, a much more effective deterrent than anything DARE could have dreamed up? There’s the body horror of Jared Leto’s Harry shooting up in an arm that’s more wound than limb; there’s the operatic nightmare of that bravura final sequence, a hallucinatory nightmare in which each of the film’s four main characters sink to their lowest points (especially Jennifer Connelly’s poor Marian). But mostly, there’s Ellen Burstyn, a fragile wonder as Harry’s lonely, diet-pill-popping mother, Sara. Her gradual breakdown is both riveting and unbearable—the sort of performance you can’t stop watching but never want to sit through a second time. —Hillary Busis

The Mist (2007)

A strange white cloud envelopes a small town, trapping a group of residents inside a grocery store. No big deal, right? Except there’s something out there. Some things. And they are large, hungry, and virtually undetectable until they strike. Stephen King’s novella was first published in 1980, and it had always been a fan favorite, a literary variation on creature features of the 1950s like The Blob and Them. After previously adapting King with The Shawshank Redemption and The Green Mile, director Frank Darabont turned this monster mash into a post-9/11 metaphor about what happens when we let fear overpower reason. The brave fare well in The Mist, while those who give in to panic or terror inevitably meet gruesome fates. The ending is the perfect summation of this, but it stands as a notoriously harrowing and disturbing finale. And while it differs from King’s ending, the writer himself has said he wished he had come up with it: “The ending is such a jolt—wham!—it’s frightening. But people who go to see a horror movie don’t necessarily want to be sent out with a Pollyanna ending.” — Anthony Breznican

Blue Valentine (2010)

Forget what Nicole Kidman said in that AMC ad: Heartbreak actually feels bad in a place like this. Blue Valentine stars Michelle Williams as Cindy, an ambitious med student, and Ryan Gosling as Dean, an alcoholic high-school dropout. Their unexpected romance begins with electric chemistry that erodes over time, leaving them in a dysfunctional and ultimately untenable marriage. A story told in the vein of Jason Robert Brown’s musical The Last Five Years, Blue Valentine jumps between two narratives, shifting back and forth in time to show us the high highs and low lows of Dean and Cindy’s relationship. Writer and director Derek Cianfrance has made a name for himself in the “feel-bad” genre, having helmed Sound of Metal and The Place Beyond the Pines in the years since—but in Blue Valentine, only his second feature film, Cianfrance proved his bonafides. Blue Valentine will take you on an emotional roller coaster as it charts every stage of a doomed relationship, from blissful beginning to excruciating end. Also, there’s a dead dog. —Chris Murphy

The Social Network (2010)

Aaron Sorkin’s incisive acidity pairs well with David Fincher’s penchant for dark underbellies, creating an origin story that only gets bleaker with age. The Oscar-winning film chronicles Facebook’s inception, the days when it was merely a collegiate disruptor and its most insidious chapters had yet to be written. As played by Jesse Eisenberg, there is something quaint about Mark Zuckerberg showing up to business meetings in “fuck-you flip-flops” and whispering pithy insults across board rooms, given the far more sinister influence his creation (or acquisition, as Eduardo Saverin and the Winklevoss twins would argue) has had in the almost two decades since. Although there’s something amusing about imagining Zuckerberg all this time later, still listlessly waiting for Rooney Mara to accept his friend request. —Savannah Walsh

Melancholia (2011)

Maybe it’s the slow-motion climate crisis, or the ongoing quagmire of war, or AI uncertainty amid mass layoffs—but right about now, the downbeat plot of Melancholia, Lars von Trier’s film about a wayward planet’s impending destruction, has a comforting simplicity. Who can blame a big rock? Von Trier took inspiration from a phenomenon he learned about in therapy: that depressive people sometimes remain eerily calm during moments of catastrophe, as they’re already practiced in expecting the worst. Kirsten Dunst assumes that role here, as a radiant bride turned stoic clairvoyant. Charlotte Gainsbourg plays her sister, who is shattered by the doomsday news. (Gainsbourg also stars in Antichrist and Nymphomaniac, which together comprise von Trier’s so-called Depression Trilogy.) Melancholia’s imagery—horseback riding through fog, nude moonbathing—has an operatic grandeur, dressing up the otherwise disquieting anticipation. In a sense, the big-picture takeaway comes from the anti-marriage tirade delivered by the mother of the bride (a withering Charlotte Rampling): “Enjoy it while it lasts.” —Laura Regensdorf

Young Adult (2011)

As the end credits roll, Diana Ross sings, “We don’t have to change at all”—a sentiment from her 1973 song “When We Grow Up” that Charlize Theron’s Mavis has embraced. At the beginning of Diablo Cody’s script, the former prom queen is a chronically depressed writer whose daily ritual of chugging Diet Coke by the two-liter and mainlining bad reality TV is interrupted only by an ill-conceived plot to wreck her high school sweetheart’s home. After failing on this front, Mavis flings herself from the arms of her ex (Patrick Wilson) to those of the cynical former classmate with whom she finds unlikely kinship (Patton Oswalt). She flirts with a fresh start, but after getting her dysfunctional viewpoint reinforced by a separate character, Mavis slips back into her wine-stained dress from the night before and rejects any sort of redemption. Director Jason Reitman insisted on this bitter ending, he once said, because in real life, “assholes don’t change like they normally do in the third acts of movies.” —Savannah Walsh

Amour (2012)

The protagonists of the second Michael Haneke film on this list have nearly the same names as the main characters in Funny Games: they’re Georges (Jean-Louis Trintignant) and Anne (Emmanuelle Riva), a pair of long-married musicians now in their twilight years. But that’s about where the similarities end. Where the earlier film is cold and sneering, Amour is, if not warm, tender and compelling as it elegantly charts the deterioration of Anne’s health and Georges’ efforts to care for her despite his own advanced age. Their gradual declines are painful to sit through but impossible to look away from. —H.B.

The Act of Killing (2012)

The Act of Killing meditates on the very notion of a feel-bad movie by asking its subjects to essentially make one out of horrific true events—and observing them do it with a smile on their face. This revelatory documentary from Joshua Oppenheimer follows various retirement-aged individuals, who, decades earlier, participated in the mass murders of millions of Indonesian people. We encounter this group not remorseful or repressed, but prideful—eager to recount what they did. Oppenheimer collaborates with these men on a series of reenactments as they gleefully make cinematic spectacle out of barbaric acts of violence. They result in sequences so darkly comic in their horrific realism, so divorced from what we think of as a standard moral compass, that they speak singularly to film’s power of depiction—because, in these killers’ mind, Hollywood epics and actual genocide aren’t so far apart. The Act of Killing presents a thesis on movies’ capacity to make us feel bad, yes, but it also interrogates what lies beneath when they make us feel good. —D.C.

Fruitvale Station (2013)

Based on the true story of Oscar Grant, a young man killed by a police officer in Oakland, CA, Fruitvale Station follows Grant on the last day of his life. The little moments of what starts out as an ordinary day fill the viewer with dread for what’s to come. A riveting and sensitively told story, Fruitvale Station continues to remain relevant even years later as Black men continue to lose their lives at the hands of police. And though a devastating watch, the film will forever hold a significant place in cinematic history as Ryan Coogler’s introduction to the world, as well as establishing Michael B. Jordan as a talented leading man who was able to deliver a nuanced performance full of yearning and despair. —Rebecca Ford

Foxcatcher (2014)

Before there were the doomed wrestling brothers of The Iron Claw, there were the doomed wrestling brothers of 2014’s Foxcatcher. When the movie was released, much of the attention focused on Steve Carell’s transformative performance (fake nose included)—but the heart of the movie is the tender, relationship between brothers Mark (Channing Tatum) and David Schultz (Mark Ruffalo), who accept the largesse of Carell’s wrestling fanatic millionaire John du Pont with disastrous consequences. Occasionally darkly funny but mostly miserable, it’s a showcase for excellent performances and Bennett Miller’s direction that might make you feel awe for the artistic accomplishment in addition to all those bad vibes. —K.R.

Manchester by the Sea (2016)

Death, grief, self-hatred, failure, and landscapes both literally and figuratively frozen have never possessed more cathartic beauty than they do in this misery-packed masterpiece from writer-director Kenneth Lonergan. Playing an emotionally shattered janitor who reluctantly attempts to care for his dead brother’s teenage son (Lucas Hedges, in his breakout role), Casey Affleck is basically the Greek god of not being able to get your shit together after a crushing tragedy. But it’s feel-bad MVP Michelle Williams, in her showcase scene as his estranged ex-wife, who will drain your tear ducts and leave you weirdly awestruck by the sheer courage it takes for each of us to get through a damn day in this crazy, wounding world. Too many films about suffering end up leaving you numb; this one actually opens your heart. Come to think of it, I’m about due for a rewatch! —Michael Hogan

Hereditary (2018)

Ari Aster is arguably American film’s preeminent feel-bad director, fashioning stories about mommy issues and the worst boyfriend in history into riveting, darkly funny epics. But none of his movies will make you feel worse than his first feature, the movie that arguably turned “elevated horror” into its own quasi-genre. It’s become cliché to claim that a horror movie is actually about trauma, but that’s also largely thanks to Hereditary, an almost intolerably unpleasant watch focused on artist Annie Graham (Toni Collette, really going for it) and the familial tragedy she’s apparently destined to endure. All that, plus one of the gnarliest child deaths ever captured on film, make clear why Annie really, really does not want to be asked if she’s okay. —H.B.

Uncut Gems (2019)

Have you ever felt more anxiety while watching a movie than the first time you saw Uncut Gems? Watching A24’s absurdly stressful indie, directed by the Safdie brothers and starring a never-better Adam Sandler, feels akin to walking a tightrope over a pool of sharks while being pursued by a bear. A gambling addict and jewelry store owner in Manhattan’s diamond district, Sandler’s Howard Ratner repeatedly risks everything to pay off his many debts, which include $100k that he owes his brother-in-law Arno (Eric Bogosian). Along the way, Howard gambles and schemes as he juggles his accounts, his wife Dinah (Idina Menzel), his kids, NBA superstar Kevin Garnett, pop star Abel “The Weeknd” Tesfaye (turning in a performance that puts his work in the ill-fated The Idol to shame), and of course, Josh Safdie’s muse Julia Fox, in a star-making turn as Howard’s girlfriend. The Safdie brothers’ frenetic style and Daniel Lopatin’s pulsating score only amplify the chaos. Sandler was simply robbed of a leading actor Oscar nomination that year—but you can bet your last buck that, if you watch him in Uncut Gems, you’re in for an awesomely feel-bad time. —C.M.