Comedies are generally meant to be light and breezy entertainment and this certainly the case for most modern Hollywood releases. No matter the style of humor, the runtime, or the weight of the subject matter, comedies are, generally speaking, naturally fast-paced examples of entertainment that attempt to ensure their viewers leave with smiles on their faces. Some comedies, however, will intend to make you feel guilty about why you’re laughing. These are the films that revel in pitch-black tones and making light of very serious and often taboo themes, delighting in each shamefaced chuckle and every giggle flavored by tinges of cringing.

Some may consider such humor inappropriate, and while these detractors aren’t objectively wrong, inappropriate humor such as this can be important. In a way, accepting and engaging in dark humor is a form of catharsis. Boundaries are there to be tested, not to confine us. For these 20 films, not only are boundaries tested, poked, and prodded: they’re gleefully crossed.

18. Sightseers (2012)

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Though his most recent and biggest film yet, High-Rise was released not too long ago, Ben Wheatley is still a director on the rise. Based upon previous releases like Kill List, Wheatley is a fan of brutal violence, and while Sightseers certainly fills that check box, it has the added benefits of some well-written pitch black humor from its two lead stars and writers, Alice Lowe and Steve Oram. What starts out as a simple holiday for a young couple (Lowe and Oram) devolves into something more foul as they commit a murderous rampage against fellow tourists.

What’s remarkable about Oram and Lowe’s performances as Chris and Tina, respectively, is the subtle way in which they express victimization and victimhood in spite of the predicaments that they, to put it mildly, create for themselves. It’s a twist on the “us against the world” mentality that’s oddly romantic – at least, until the cracking final scene that will leave you grasping for air in laughter.

17. Fargo (1996)

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Hannah Arendt may have coined the concept “the banality of evil,” but in Fargo, the Coen brothers mostly make evil look benign. Between the fumbling Jerry Lundegaard (William H. Macy) and the criminal odd couple of Carl (Steve Buscemi) and Gaear (Peter Stormare), the film’s antagonists hardly make for something intimidating, beside from those moments when Gaear takes charge.

If anything is banal, it’s the Coen brothers’ depiction of small town America. Everything from everyday conversation, to routine investigation of a multiple homicide is presented as purposefully dull, but the prominence of the regional accent in dialogue prevents proceedings from being entirely bland. The comical degree to which the accent is highlighted may be enough to make anyone feel slightly bad about chuckling – especially if they are from the northern central states – but Buscemi and Stormare are an equally rich source of non-regretful entertainment. Gaear may be a stoic, stone-cold criminal, but Carl’s lack of grace – especially when confronting Jerry’s father-in-law – undercuts any intimidation factor.

16. Seven Psychopaths (2012)

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Martin McDonagh may be only two feature films into his directorial career, but with Seven Psychopaths, it’s clear that his narratives and dialogue involve an eclectic mix of personalities and spot-on characterization, which isn’t a bad thing by any stretch of the imagination. Colin Farrell, whom he had previously worked with on In Bruges, is game for a different sort of role – playing the straight man while new collaborators Sam Rockwell and Christopher Walken provide the zany pizazz.

McDonagh may not be one for conventional storytelling and Seven Psychopaths seems a resounding middle finger to it. Even though the film is under two hours in length, McDonagh still takes a considerable amount of time creating fictional narratives and characters for his leads to spin. The main characters concoct increasingly complicated ways to kill each other and you can’t help but laugh. The screenplay also sets its sharp teeth into stereotypical Hollywood stories and the people they attract, which seems appropriate given his take on the characters that populate crime dramas in In Bruges.

15. Cheap Thrills (2013)

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The Germans were onto something when they created a word that expressed pleasure at another person’s misery, that word being “schadenfreude.” As far as the horror genre is concerned, such a concept is suited to a sub-genre like so-called “torture porn,” but even the most hardened genre fan can only find so much enjoyment in such low places. Whether that be because the film actually pushes the boundaries too much, like A Serbian Film, or the formula becomes tired, like the Saw franchise, that pleasure wears thin.

Enter Cheap Thrills, a pitch-black comedy about two desperate friends participating in a game of escalating truth or dare to make some quick cash, despite how twisted these dares become. By injecting humor within and around of the margins of graphic violence, the film, for the most part, takes away the occasional discomfort of watching something like torture porn. At the end of the day, however, you’re still watching to people willingly resort to personal and physical agony.

14. Fight Club (1999)

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In all fairness, most, if not all, of Chuck Palahniuk’s bibliography is conducive to lists such as this one, and of the adaptations of his work, Fight Club sits atop the pile, thanks to David Fincher’s handiwork. Palahniuk’s material thrives on perversity and active rebellion against convention and Fincher provides the grimy, pessimistic visual and narrative tone to match. The eccentric personalities who inhabit this story, especially Tyler Durden (Brad Pitt) and Marla Singer (Helena Bonham Carter), represent that rebellion against storytelling, which carries over into the film’s – and novel’s – non-conformist rhetoric.

Fight Club is an endlessly quotable film, and many of those lines of dialogue are the same ones that would have made anyone squirm in their seat while simultaneously sending them into rapturous laughter; one particular line from Carter’s Marla illustrates this perfectly. In fact, compared to many of the other films on the list, Fight Club demonstrates that darkness and taboo humor can be accessible.

13. An American Werewolf in London (1981)

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An American Werewolf in London was certainly a sharp left turn for director John Landis, who was continuing to ride the waves of success fomented by Animal House and The Blues Brothers. Between the initial werewolf attack on the English moors and David’s first night out as a werewolf, it is a genuinely frightening flick – not to mention special-effects artist Rick Baker’s famous transformation sequence that ranks with the best of them. But coming as it does from Landis, the film is plenty funny, and one particular aspect of the film’s narrative will surely tickle someone pink.

In his multiple visits to David (David Naughton) as one of the “undead,” Jack (Griffin Dunne) tries to convince David to kill himself to end the werewolf madness. Dunne plays it with an even mixture of cheekiness and gravitas, and though the joke is repeated a couple of times, it’s most funny the final time as David tries hiding in a Piccadilly Circus “adult” theater, all while his victims from the night before joyfully hypothesize the many ways David could take his own life.

12. Heathers (1988)

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Somehow, it seems only fitting that Heathers screenwriter Daniel Waters is the older brother of Mean Girls director Mark Waters. In addition to Mean Girls’s Tina Fey, Clueless’s Amy Heckerling, Diablo Cody for Juno and Jennifer’s Body, and Kevin Williamson of the Scream franchise, Waters used dialogue to tap into how high schoolers feel about themselves in their fantasies.

In any of the films listed, it doesn’t take long for a least one character to demonstrate an acerbic wit that appropriately suspends belief. With Heathers, however, the elder Waters gave his humor a dark, twisted edge that simultaneously exposes the ugly truths about high school kids, while still giving them an elevated platform to stand on. One of the best examples in the film is Heather Chandler’s funeral, as the kids come up to her open wake and silently address God. It’s filled with all of the vanity one might expect to find, but the context makes it that much more devilish.

11. Deadpool (2016)

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Now this was the Deadpool fans had been screaming about for so long, not that poor representation – although still played Ryan Reynolds – of Wade Wilson who made an appearance in X-Men Origins: Wolverine. Deadpool is known for his snarky and often-dark sense of humor that gracefully mingles with immaturity, and, though the humor in Deadpool is quite immature, the titular anti-hero’s charming, acidic onscreen presence tells the audience that it’s okay to indulge in darker comedic tastes.

Though, without Deadpool’s peculiar personality, Deadpool would have just been any other superhero movie, underscoring his importance in not just the Marvel canon, but also the superhero genre. Most of his humor is more tastelessly juvenile than dark and subversive, but Wilson shares more than handful of moments where he can test the limits, as is appropriate for his character. Additionally, because Deadpool continues to be one of the year’s highest grossing pictures more than halfway through the year and right in the thick of summer releases, don’t be surprised to see more of this ilk in the future.

10. American Psycho (2000)

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American Psycho is perhaps the only film – or novel, for that matter – that could convince its audience that a business card is a phallic symbol. Early on in the film, when Patrick Bateman (Christian Bale) and a few of his business associates whip out their cards to compare, the increasing inferiority that makes Bateman sweat straddles the line between amusing and disquieting, coming out slightly on the side of the former. It’s just one scene among many in this Mary Harron that thoroughly dissects alpha male business culture and 1980s yuppie-ism.

And of course, while Bale’s performance as Bateman is often disturbing in his volatile insanity, the zany goofiness with which he presents himself is intoxicating. Instead of distracting the viewer from the pure rage of his murderous tendencies, the nerdy, sometimes academic façade he puts up accentuates his psychotic nature. Additionally, while it alienates him from his colleagues, that alienation highlights the absurdity of their behavior, which is more reminiscent of business-style machismo. Even after he kills a homeless man, his dog, and countless others, we still find room to laugh.

9. The Guard (2011)

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John Michael McDonagh’s The Guard is nothing but fun; it’s part Irish western, part buddy cop movie, and part dark comedy. Its two leads, Brendan Gleeson and Don Cheadle may exhibit strong chemistry, but it all comes together through Gleeson’s performance as Sergeant Gerry Boyle. There are your archetypal corrupt cops and then there’s Gerry Boyle. Sure he’s confrontational, often offensive on many levels, and gripped by numerous vices, but his frequent obliviousness to the negative effects it all has is, at least in this case, charming and hilarious.

Much like his brother Martin, who directed Seven Psychopaths, the dialogue in McDonagh’s films – especially this one – carries the same appeal. For example, a small group of characters will interact for a reason that might normally be over in the blink of an eye, but then one character says or does something nonsensical, and they’re all stuck talking about it for a minute or two. While anyone might normally see that tactic as intentional meandering and padding the runtime, in a way, it’s an effective method of pastiche that reduces the glamor of the scene.

8. In Bruges (2008)

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Martin McDonagh’s In Bruges contains a deeply heartfelt story with a tragic ending that leaves the viewer with a satisfying emptiness. Thanks to one of its protagonists, Ray (Colin Farrell), who is refferred to by his partner Ken (Brendan Gleeson) as the worst tourist in the world, it’s also pleasantly absurd and profane, garnering cult status through its dark humor and clever dialogue.

In McDonagh’s film, it all comes down to strong characterization. Ray takes no prisoners in his seemingly constant verbal abuse, as can be seen in his remarks to Ken about Bruges compared to Dublin and in his encounter with a heavy-set group of strangers. His almost childlike lack of a filter is delightful, and for some, perhaps even quite enviable. His boss Harry (Ralph Fiennes) is a bit more ruthless in his insults, but he still possesses the same painful honesty. Truth be told, most of the character’s mouths are loaded with something offensive to say.

7. The Producers (1968)

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There’s very little that can compare to early Mel Brooks. With such titles as Blazing Saddles and Young Frankenstein, his delirious mind found its prime during the 70s, but it all started with his first directorial feature, The Producers. The film features the talents of Zero Mostel and Gene Wilder as Max Bialystock and Leopold Bloom, respectively. Brooks’s pen is scathing, if also celebratory in numerous respects, as the actors both revel in material that takes Broadway business and personalities down a notch and gleefully take part in convention.

As most of you probably know, the most offense taken will probably be during the musical within the film, “Springtime for Hitler.” The numbers are outrageous, but in the context of the rest of Brooks’s film, one of the world’s most evil dictators is nothing more than the butt of a joke. The film has had a peculiar history of adaptations, having been adapted for Broadway by Brooks, using Nathan Lane and Matthew Broderick for the leads, and then remaking his film based upon the adaptatio. Both are worth your time if you’re looking for a dark chuckle.

6. Tropic Thunder (2008)

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Even if it were the only option relevant example from the film, we could have left this entry for Tropic Thunder with Robert Downey Jr.’s performance as Kirk Lazarus and still satisfyingly considered it a worthy inclusion. Thankfully, there is so much more to this movie, just what you would expect from a movie lampooning the film industry in general and specifically, superstars looking to reshape their image with serious roles.

In addition to Downey Jr.’s performance is the context for Ben Stiller’s character Tugg Speedman, a fading action movie star who had previously tried keeping his career on track by portraying the mentally challenged “Simple Jack” – which garnered real life controversy from advocacy groups before Tropic Thunder’s release. The material is certainly offensive, but during the scene when Lazarus explains to Speedman that actors should never go “full retard,” it is an uncomfortably sharp and hilarious criticism of actors who use disabilities for their own personal gain.

5. American Beauty (1999)

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There’s something inherently fun about watching an already emotionally tested family with a bevy of rocky relationships continue to gloriously sink further into the rabbit hole. When we first meet Lester (Kevin Spacey), he un-emphatically states that his sad alone time in the shower will be the highlight of his day and, as he strides toward making his individual life better, the rest of his family continues to fall apart in their own fashion.

The dichotomy of prototypical suburban American life decaying while one person attains clarity, peace, and newfound confidence through pursuit of personal truth is only the beginning of this roller coaster. Consider the subplot in this film that pushes the main narrative forward: Lester becoming infatuated with his daughter Jane’s (Thora Birch) friend Angela (Mena Suvari). It’s certainly a creepy setup, undercut by stylish fantasies and an almost awkwardly youthful performance from Spacey, but then it’s made even creepier – and thereby funnier – when Angela sheepishly tries to seduce Lester by the film’s end.

4. You’re Next (2011)

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Honestly, home invasion thrillers are one of the best genres to write dark humor for. Home invasion villains would rather play with their victims before dispatching them, rather than getting the endgame out of the way, so some Freddy Krueger-esque tongue-in-cheek cleverness would be an acceptable route. Besides, for the most part, the genre is more lifeless than the victims its films rack up. So what do you get when you mix a home invasion thriller, dark humor, and Home Alone? Well, you do get You’re Next, but more importantly, you get an entertaining subversion of the home invasion genre.

First of all, miraculously, almost no one here can be considered a sympathetic character. Otherwise, you are anxiously waiting for their demise, which might sound like a dreadful experience, but it’s a nice change of pace compared to the rest of the genre. Additionally, when the humor gets dark, it gets pitch black. Zee’s (Wendy Glenn) proposition to her boyfriend right next to his dead mother, in particular, is a riot.

3. Team America: World Police (2004)

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It’s all in the theme song, which is merely a simple three words: “America! F— yeah!” Every ounce of creativity Matt Stone and Trey Parker used to give American foreign policy a good kick in the rear in their feature length South Park movie, they expanded into a 98-minute runtime and got some help from Seth MacFarlane for Team America: World Police. It’s every bit as absurd and rude as South Park, and the puppets seem to drive that point home – especially when they poke fun at conventional action movie fight scenes with silly puppet brawls.

What’s probably most significant about the film is its poking fun at Middle Eastern people, a bold and potentially moronic comedic move considering the anti-Islamic sentiment that began to boil even in the earliest years of the war in the Middle East. And as The Interview made clear a couple of years ago, we still like to take swipes at North Korea every now and then, and this film even devotes an entire musical number to the inability of making ‘l’ sounds.

2. South Park: Bigger, Longer & Uncut (1999)

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Leave it to the creators of South Park to make light of any taboo or timely subject and reduce their audience to tears at the same time. They’ve long used the television show as a platform for critical satire, and Bigger, Longer & Uncut is some of their best work. The “kill list,” so to speak, in this film includes censorship, American foreign policy – which would get another rousing, more thorough send-up in Team America: World Police – and parents who aren’t able to accept the blame whenever an issue with their child arises.

Running at a speedy 81 minutes, it’s short, blunt, and to the point. The satire is abundant and yet there are no frills, a commendable quality indeed. While America and Canada wage war over the imprisonment and impending execution of sophomoric Canadian comedians, the homosexual Devil – which is pretty on the nose considering the archaic rhetoric regarding homosexuality that would have persisted in the 90s – looks to break free from his abusive relationship with Saddam Hussein. It’s simply too rich to ignore. Also, the “Kyle’s mom” musical number is one of the more delightful songs to be heard from a narcissistic elementary school child.

1. Poultrygeist: Night of the Chicken Dead (2008)

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Now, first of all, if you were previously aware of the existence of Poultrygeist: Night of the Chicken Dead, odds are you’re a fan of Troma Entertainment and the wonderful work they do. Secondly, if you try foisting Poultrygeist onto Troma virgins, there are only two possible outcomes: either your friends will carry you out on a throne and sing your graces, or they will forever judge your movie choices and you’ll have to work to regain their trust.

Such is the risk one takes with any Troma feature, but Poultrygeist seems special in this regard. It’s equally as fun as something like Evil Dead II – and in a very similar vein – but it’s even more juvenile, offensive, and completely tasteless. That, however, is part of Troma’s appeal. Additionally, like many other Troma films, Poultrygeist possesses some poignant social commentary that just happens to be nearly shrouded by farce. Finally, as if it couldn’t get any better, it’s a decently catchy musical filled with songs as bewildering and vulgar as any of the jokes made at the expense of the fast food industry or the American dream.

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