Many comedic films deal with everyday relatable subjects like dating, relationships, family dynamics, and office politics. These allow the audience to laugh at life without really having to worry about any of its strife.
But another class of comedy goes in the opposite direction, finding humor in some of the darkest subjects imaginable, like war, genocide, political scandal, disease, abortion, and more. Often, this requires comedians and filmmakers to explore the line between what’s acceptable to joke about and what’s in poor taste. The best examples of this kind of comedy make you laugh about the worst horrors in life while also making you think about their implications - but they don’t make you feel gross for having laughed.
To be clear, comedy is subjective, and one person’s classic comedy might be another person’s tasteless schlock. The comedies on this list all have legions of fans, but plenty of critics, too. Like all great art, they prompt debate.
The Tricky Topic: The Vietnam War
The Premise: Robin Williams stars as Adrian Cronauer, a real-life DJ for the Armed Forces Radio in Vietnam, who bucks the system by providing satirical and honest radio broadcasts for the troops about the war. His ability to influence the situation proves limited when he falls in love with a Vietnamese woman whose brother belongs to the Viet Cong.
How It Finds The Funny: It stars Robin Williams, the king of improv. But the film was also released in 1987, 12 years after the end of a divisive war. It doesn’t trivialize the Vietnam War’s horrors, but it does poke fun at the war’s futility, while still honoring the sacrifices made on both sides.
- Actors: Robin Williams, Forest Whitaker, Tung Thanh Tran, Chintara Sukapatana, Bruno Kirby
- Released: 1987
- Directed by: Barry Levinson
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The Tricky Topic: WWII and the Holocaust
The Premise: During the fall of Germany in WWII, 10-year-old Jojo has become so indoctrinated by Nazi ideals that his imaginary friend is literally (a silly version of) Adolf Hitler. But when he discovers his mother hiding a Jewish refugee in their home, it forces him to question everything - including his imaginary friendship.
How It Finds The Funny: Jojo Rabbit is based on Christine Leunen’s 2008 book Caging Skies, and according to writer-director Taika Waititi, the first draft of the screenplay wasn’t particularly funny and didn’t even include the Hitler character. Waititi remedied this by adding an imaginary Hitler who’s almost childlike in his ridiculousness, reflecting Jojo’s innocent point of view. As Jojo becomes disillusioned, Imaginary Hitler becomes more like the one we all recognize - and the movie stops being quite so funny.
- Actors: Roman Griffin Davis, Thomasin McKenzie, Scarlett Johansson, Taika Waititi, Sam Rockwell
- Released: 2019
- Directed by: Taika Waititi
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The Tricky Topic: Cancer
The Premise: Loosely based on the real-life experience of screenwriter Will Reiser, 50/50 tells the tale of a radio producer who contracts a rare form of cancer, which forces him to reevaluate everything in his life. In the end, the experiences transform him into a stronger person.
How It Finds The Funny: “Cancer” doesn’t immediately scream “hilarious,” but it helps to have Seth Rogen on board, who was friends with Reiser when he underwent his experience. While 50/50 doesn’t shy away from the difficult moments, it also finds lots of humor in the situation, from the bodily humiliations illness gives us to the absurd things well-meaning people say to cheer sick people up.
- Actors: Joseph Gordon-Levitt, Seth Rogen, Anna Kendrick, Bryce Dallas Howard, Philip Baker Hall
- Released: 2011
- Directed by: Jonathan Levine
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The Tricky Topic: American lobbying
The Premise: Set in the early 2000s, Nick is one of the best lobbyists on Capitol Hill and a shill for Big Tobacco. He insists there’s no link between smoking and cancer, and he’s so persuasive you almost believe him. As he rises to the top of his profession, he tries to avoid consequences for his actions as well as provide a good role model for his son. In the end, Nick can’t avoid Big Tobacco from forking over a multimillion-dollar class action settlement, but he still emerges relatively unscathed.
How It Finds The Funny: Sometimes you want to revel in an antihero, and even though we know Nick is in the wrong, it’s still fun to see him take down one self-righteous opponent after another. It’s also a refreshingly honest look at the forces that shape American government and society. Even though Nick and his cohort end up winners, you can still take comfort in the confirmation that special interest groups are as evil as they’re made out to be.
- Actors: Aaron Eckhart, Maria Bello, Cameron Bright, Adam Brody, Sam Elliott
- Released: 2005
- Directed by: Jason Reitman
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The Tricky Topic: Mental illness (specifically bipolar disorder)
The Premise: After an eight-month stint in a mental hospital for assaulting his wife’s lover, Pat tries to find a new outlook on life by finding the “silver lining” in every situation. At first, he’s determined to win his wife back, but when a fellow mentally afflicted person, Tiffany, enters his life, he questions everything. Pat and Tiffany attempt to rebuild their lives and get a fresh start, which culminates in a dance competition that also could help Pat’s father start a restaurant.
How It Finds The Funny: This one definitely leans more into the “drama” half of its dramedy label, but it does have quite a few chuckles throughout. Pat and Tiffany are both presented as intensely awkward people, and the movie mines plenty of humor out of their struggles at interacting with non-mentally afflicted people. Yet it never trivializes or makes light of mental illness, instead presenting it as a fact of life.
- Actors: Bradley Cooper, Jennifer Lawrence, Robert De Niro, Jacki Weaver, Chris Tucker
- Released: 2012
- Directed by: David O. Russell
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The Tricky Topic: Nuclear warfare
The Premise: During the height of the Cold War, an American Air Force General named Jack D. Ripper goes insane and orders a preemptive strike on the Soviet Union. As cooler heads try to prevail, it becomes clear that the rest of the top-level leadership in both counties isn’t much more cogent than the general is. Spoiler: they can’t fend off nuclear Armageddon.
How It Finds The Funny: Here’s another film that borrows from The Great Dictator by presenting war as an exercise in absurdity, right down to the names like Jack D. Ripper, Col. “Bat” Guano, and Major T.J. “King” Kong. Almost all characters are either venally corrupt, insane, or some combination of both. It also stars comedy legend Peter Sellers in multiple roles.
- Actors: Peter Sellers, George C. Scott, Keenan Wynn, Slim Pickens, Peter Bull
- Released: 1964
- Directed by: Stanley Kubrick
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The Tricky Topic: American imperialism
The Premise: A Broadway actor, Gary Johnston, is recruited to join an elite squad of American commandos tasked with hunting down and killing America’s enemies at any cost - even if it means, for example, blowing up Paris. However, the bigger enemy might just be the echelon of Hollywood elites collectively known as the “Film Actor’s Guild,” whose initials should tell you everything director Trey Parker and co-writers Parker, Matt Stone, and Pam Brady think about Hollywood activism.
How It Finds The Funny: For starters, there’s just something inherently hilarious about portraying the War on Terror via a bunch of marionettes, and the film uses this conceit to its full potential - just check out the love scene between Gary and his squadmate Lisa. But also, in true Parker-Stone fashion, the film pokes fun at all sides in the controversial War on Terror, favoring none of them.
- Actors: Trey Parker, Matt Stone, Kristen Miller, Masasa Moyo, Daran Norris
- Released: 2004
- Directed by: Trey Parker, Matt Stone
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The Tricky Topic: Armageddon
The Premise: Two astronomers discover that a comet will hit Earth in six months and wipe out civilization. But the bigger problem is convincing anyone to do something about it. Metaphor for climate change? Yes, yes it is.
How It Finds The Funny: Imagine a movie like Armageddon or Deep Impact, but practically everyone in charge is a self-obsessed boob instead of a competent technocrat. Even the people who are willing to try to stop the comet, like Mark Rylance’s billionaire tech mogul, are insane too.
- Actors: Leonardo DiCaprio, Jennifer Lawrence, Meryl Streep, Rob Morgan, Jonah Hill
- Released: 2021
- Directed by: Adam McKay
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The Tricky Topic: Nazi Germany
The Premise: Parodying the rise of the SS, Charlie Chaplin plays two parts: a not-even-thinly veiled caricature of Hitler named Adenoid Hynkel and a hapless Jewish barber who strongly resembles him. As the barber and his love interest Hannah try to escape persecution by “Tomainian” (i.e., German) forces, a misunderstanding results in the barber taking control of Tomainia and bringing peace to Europe.
How It Finds The Funny: The Great Dictator was released in 1940, just after Germani invaded Poland and started WWII in Europe. Fearless in its willingness to present some of the world’s greatest villains as utter morons, it was one of the first films that allowed audiences to laugh at Hitler and his cronies rather than fear them, starring arguably the world’s greatest comedian at that point.
Even though the film is a masterpiece of filmmaking as well as a call to action that inspired the world to fight Nazism, it’s also worth noting that Chaplin himself felt conflicted about how he handled the subject. He wrote in his 1964 autobiography:
Had I known the actual horrors of the German concentration camps, I could not have made The Great Dictator; I could not have made fun of the homicidal insanity of the Nazis.
- Actors: Charlie Chaplin, Paulette Goddard, Jack Oakie, Reginald Gardiner, Henry Daniell
- Released: 1940
- Directed by: Charlie Chaplin
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The Tricky Topic: The Soviet dictatorship
The Premise: Following the sudden death of Josef Stalin in 1953, various members of the Soviet political machine vie for control of the country, while also trying to save their own skins from the regime’s brutal reprisals.
How It Finds The Funny: This one is directed and co-written by Armando Iannucci, who’s responsible for some of the most critically acclaimed comedies of the 21st century like Veep, In the Loop, and I’m Alan Partridge. Like his other work, The Death of Stalin presents powerful political figures just as bumbling and venal as the rest of us. Plus, in true Iannucci style, practically every line is a well-crafted joke.
- Actors: Steve Buscemi, Simon Russell Beale, Jeffrey Tambor, Paddy Considine, Rupert Friend
- Released: 2017
- Directed by: Armando Iannucci
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The Tricky Topic: The North Korean dictatorship
The Premise: James Franco and Seth Rogen star as a journalist and his producer who score an interview with North Korean dictator Kim Jong Un. Things get complicated when the CIA tasks the pair with assassinating him.
How It Finds The Funny: For starters, it relies on the sturdy “fish out of water” trope, in this case shoving two media lightweights into the world of international espionage. The Interview also follows in The Great Dictator’s footsteps by presenting a buffoonish parody of a real-life despot. In this case, Randall Park’s Kim Jong Un is a seemingly misunderstood sweetheart who loves American pop culture and basketball, and just happens to oversee a murderous regime.
- Actors: Eminem, James Franco, Seth Rogen, Randall Park, Rob Lowe
- Released: 2014
- Directed by: Seth Rogen, Evan Goldberg
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The Tricky Topic: World War II and the Holocaust
The Premise: Roberto Benigni stars as Guido Orefice, a young Jewish man in Mussolini’s Italy who falls in love with a gentile and has a son, Giosue. Then Guido, Giosue, and Guido’s uncle Eliseo are sent to a concentration camp. From there, the normally lighthearted and clownish Guido shields Giosue from the horrors of their situation by pretending it’s all a game.
How It Finds The Funny: Benigni’s performance is one of the all-time great pieces of clowning in cinema, as he uses physical humor, slapstick, and general ridiculousness to keep his son laughing. Far from trivializing the Holocaust, it honors the victims of the tragedy by presenting Guido’s actions as a comedic form of resistance.
- Actors: Roberto Benigni, Nicoletta Braschi, Giorgio Cantarini, Giustino Durano, Sergio Bini Bustric
- Released: 1997
- Directed by: Roberto Benigni
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The Tricky Topic: The bursting of the housing bubble in the United States and the ensuing economic recession of 2008.
The Premise: The Big Short is told from the perspective of employees at three financial companies, who gradually come to realize there’s an oncoming crisis and scramble to make as much money as they can off it.
How It Finds The Funny: This was one of Adam McKay’s first forays into political comedy, and he used it to establish his unique directorial style - which pretty much boils down to presenting powerful people as overgrown children, then making it clear via superimposed text when the story isn’t exaggerating. Particularly entertaining is McKay’s use of celebrities like Anthony Bourdain, Selena Gomez, and Margot Robbie to break down the esoteric financial terms by direct-to-camera presentations.
- Actors: Steve Carell, Ryan Gosling, Christian Bale, Brad Pitt, Marisa Tomei
- Released: 2015
- Directed by: Adam McKay
Seriously funny?- 14
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The Tricky Topic: The impeachment of Richard Nixon
The Tremise: Two average 15-year-old girls inadvertently find themselves mixed up in a scandal when they witness the Watergate break-in, then get hired as Nixon’s personal dog walkers. In the end, they prove to be the key to Nixon’s downfall.
How It Finds The Funny: The whole premise is a joke, isn’t it? Dick was released in 1999 before Deep Throat was revealed to be FBI associate director Mark Felt. The idea that two pot-loving teens could play such a major role in American history is inherently absurd - imagine Forrest Gump but funny. Dick also boasts an impressive cast of comedy veterans including Will Ferrell, Bruce McCulloch, Dave Foley, French Stewart, and Teri Garr.
- Actors: Kirsten Dunst, Michelle Williams, Jim Breuer, Will Ferrell, Dave Foley
- Released: 1999
- Directed by: Andrew Fleming
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The Tricky Topic: Dictatorships
The Premise: Sacha Baron Cohen plays Admiral General Haffaz Aladeen, the ruler of the fictional country of Wadiya, who travels to the US to defend his brutal dictatorship to the UN Security Council. Once there, he narrowly escapes an assassination plot and coup attempt with the help of a human rights activist, Zoey, who shows him the error of his ways. His redemption isn’t quite complete, however, as he continues being the ruler of Wadiya, just a slightly less brutal one.
How It Finds The Funny: The Dictator is quite a bit different than Baron Cohen’s other work, as it doesn’t rely on interviews with real-life political and pop culture figures and is instead a straight-up narrative. Even without that format, it speaks truth to power by relentlessly skewering the excesses of dictators. It pokes fun at everything from Aladeen’s use of female bodyguards to his cult of personality that sees him arbitrarily changing words in the Wadiyan dictionary to his own last name.
- Actors: Sacha Baron Cohen, Anna Faris, Ben Kingsley, Jason Mantzoukas, Kevin Corrigan
- Released: 2012
- Directed by: Larry Charles
Seriously funny?- 16
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The Tricky Topic: WWII and PTSD
The Premise: Catch-22 is told from the perspective of John Yossarian, an American bomber pilot who cracks under the pressure of having to fly never-ending combat missions and tries to find a means of escape from military life. Problem is, Yossarian’s rational objection to the dangers and horrors of his duty ironically makes him more fit to continue flying, as it proves his sanity. In supposedly military jargon, this is the “Catch-22” paradox that lends the film, and Joseph Heller’s 1961 novel, its title.
How It Finds The Funny: Catch-22 isn’t exactly a laugh-out-loud, joke-a-minute comedy, but it is one of the most searing satires of war. It constantly undercuts the gravity of WWII by presenting the American way of waging it as completely nonsensical, while totally ignoring the perspective of the other side. Overall, Catch-22 is the kind of film that embodies the quote, “War does not determine who is right, only who is left.”
- Actors: Alan Arkin, Martin Balsam, Richard Benjamin, Art Garfunkel, Jack Gilford
- Released: 1970
- Directed by: Mike Nichols
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The Tricky Topic: Abortion
The Premise: Jenny Slate stars as a stand-up comedian who gets pregnant after a one-night stand and decides to terminate the pregnancy. Almost as difficult is her decision to tell the father of her child, who turns out to be supportive.
How It Finds The Funny: Obvious Child presents a nonjudgmental look at women’s reproductive rights, focusing on the human impact of such a decision instead of the potential political ramifications. Writer-director Gillian Robespierre mines the subject to find plenty of awkward humor while emphatically supporting its characters.
- Actors: Jenny Slate, Jake Lacy, Gaby Hoffmann, Gabe Liedman, Polly Draper
- Released: 2014
- Directed by: Gillian Robespierre
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The Tricky Topic: Terrorism
The Premise: Four British Muslims living in Sheffield, England, want to become suicide bombers, but prove inept at the task.
How It Finds The Funny: Terrorism, and the war against it, are some of the most taboo subjects around, but director Chris Morris and writers Jesse Armstrong and Sam Bain (creators of the seminal Channel 4 sitcom Peep Show) undercut the tension by presenting four likable and relatable characters who genuinely care for each other. The movie does have life-or-death stakes, but it’s still easy to root for our four heroes, even if their mission is unconscionable.
- Actors: Riz Ahmed, Arsher Ali, Nigel Lindsay, Kayvan Novak, Adeel Akhtar
- Released: 2009
- Directed by: Christopher Morris
Seriously funny?
