Top 20 Best Dark Comedies of All Time

Top 20 Best Dark Comedies of All Time

VOICE OVER: Rebecca Brayton WRITTEN BY: Nathan Sharp
Who says comedy needs to be lighthearted? For this list, we'll be looking at the most popular and critically acclaimed dark comedy films of all time. Our countdown includes “The Wolf of Wall Street”, “Heathers”, “In Bruges”, “Kiss Kiss Bang Bang”, “Bad Santa”, and more!

Script Written by Nathan Sharp

Top 20 Best Dark Comedies of All Time

Who says comedy needs to be lighthearted? Welcome to WatchMojo, and today we’ll be counting down our picks for the Top 20 best dark comedies of all time.

For this list, we’ll be looking at the most popular and critically acclaimed dark comedy films of all time. Warning: here there be spoilers.

#20: “The Cable Guy” (1996)

“The Cable Guy” was released at an interesting time. Megastar Jim Carrey had recently starred in enormously popular comedies like “Dumb and Dumber,” and “Ace Ventura: When Nature Calls.” People were expecting another wacky Jim Carrey comedy, and what they got instead was a creepy, deliriously dark movie about an unhinged cable installer who stalks his customers. Carrey is convincingly creepy, and Matthew Broderick plays the perfect straight man foil to his chilling antics. Now that Carrey has done more dramatic work, we can look back on the movie and appreciate its qualities. And there are many.

#19: “Horrible Bosses” (2011)

For a movie starring funnymen Jason Bateman, Charlie Day, and Jason Sudeikis, “Horrible Bosses” goes to some surprisingly dark places . . .like murder and assault. The three comedians star as dejected men who hate their jobs and decide to murder their bosses. The movie explores some troubling themes, including workplace sexual harassment with the typical gender roles reversed. Well, and the fact that the protagonists are wannabe murderers. Despite all that, the screenwriting and performances wonderfully toe the line between uncomfortable and uproarious. Charlie Day’s screaming and Jason Bateman’s bewildered straight man shtick are reliably awesome.

#18: “Bad Santa” (2003)

Christmas. The time of year for gooey cookies, comfy fires, pine-scented Christmas trees, and alcoholic mall Santas. “Bad Santa” is a different kind of Christmas movie, as it follows a sex-addicted, alcoholic thief named Willy who poses as a mall Santa to case the joint. Along the way he befriends a bullied and lonely boy named Thurman. It’s the role of a lifetime for Billy Bob Thornton, who plays Willy with reckless aplomb. He’s not a likable man. At all. But the movie is surprisingly endearing, and Willy undergoes some serious character development as his relationship with Thurman deepens. It’s certainly not a movie you’d want to watch with the kids, but it’s also far funnier (and sweeter) than you would imagine.

#17: “World’s Greatest Dad” (2009)

This movie faced the same troubles as “The Cable Guy.” It’s a comedy, and it stars Robin Williams, so most people assumed that it would be A Robin Williams Comedy. You know what we mean - wackiness, weird voices, hyperactive energy, the works. What they got instead was a very morose movie about fame, popularity, and the deplorable depths that some people will go to in order to procure it. This movie came and went without much attention in 2009, yet it received near-universal adoration from critics, many of whom praised Williams’s performance and the incredibly risky subject matter. We won’t spoil what happens - just know that this movie goes to some horrible, yet fiendishly funny, places.

#16: “Kiss Kiss Bang Bang” (2005)

Shane Black has made many great movies over the years, but “Kiss Kiss Bang Bang” may in fact be his best. Or, at least his most overlooked. Robert Downey Jr. proves that he’s one of the funniest men in the business with his performance as Harry Lockhart, a thief posing as an actor who gets caught up in a murder investigation. It’s brilliant stuff. The movie is wickedly stylish, and serves as a biting, satirical send-up of pulpy hard-boiled detective stories. Despite debuting at the Cannes Film Festival and earning critical praise, this too was somewhat overlooked and underappreciated upon release. Let’s give it the credit it deserves.

#15: “Arsenic and Old Lace” (1944)

We’re going way back for “Arsenic and Old Lace,” which was released in September of 1944. The movie is adapted from a popular Broadway play, which ran for almost 1,500 performances in the early ‘40s during World War 2.. It stars Hollywood legend Cary Grant as Mortimer Brewster, a drama critic who learns that his maiden aunts are serial killers who lure lonely old bachelors to their deaths. However, that’s just the tip of this raving and utterly insane nightmare of a story. And all throughout the lies, insanity, and murder, the movie manages to be be uproariously funny.

#14: “Happiness” (1998)

Despite what the title may suggest, Todd Solondz’s “Happiness”, which revolves around the lives of three sisters, is not a happy movie. Far, far, faaaar from it. This movie puts the ‘dark’ in ‘dark comedy,’ and is filled with deeply troublesome and troubled characters, and many viewers may find it hard to sympathize with their searches for meaning. Yet the poignant and deft script, combined with the stellar performances from everyone involved, give the audience a path to feeling human connection. But this ain’t no light entertainment, even with the laughs. Many people will not like this movie, and that’s OK. But it proves that major risks often result in major rewards.

#13: “Four Lions” (2010)

Riz Ahmed leads the charge in “Four Lions,” a satirical dark comedy that explores issues of fanaticism and radicalization. He stars as Omar, a British security guard who is a member of a radicalized homegrown terrorist group from Sheffield. The terrorist group is critical of Western imperialism and aspire to suicide bomb the London Marathon. This type of content sounds crass and borderline tasteless. And it is. But it’s also a wickedly funny movie that portrays its protagonists as imbeciles and lampoons fanaticism with intelligence and grace. Who knew radicalization could be so funny?

#12: “The Death of Stalin” (2017)

You can’t really go wrong with a cast containing Steve Buscemi, Paddy Considine, Jason Isaacs, and Jeffrey Tambor. As you can probably surmise from the title, this movie concerns the death of Soviet dictator Joseph Stalin, who died suddenly of a cerebral hemorrhage in 1953. Following Stalin’s unexpected death, the Council of Ministers scramble and scheme as they all vie for power. While critics praised the satire and performances, the film was met with disdain by the Russian Ministry of Culture and was subsequently banned in Russia, Kazakhstan, and Kyrgyzstan.

#11: “The War of the Roses” (1989)

Danny DeVito both directed and stars in “The War of the Roses,” which was adapted from Warren Adler’s novel of the same name. While the movie takes its name from a historic period, the movie depicts a different kind of war - a war of love gone wrong. Michael Douglas and Kathleen Turner star as Oliver and Barbara Rose, a married couple going through a bitter divorce and a fierce battle over their shared material possessions. As the battle is prolonged, their methods to get rid of each other grow increasingly macabre. The movie is DeVito’s finest directorial effort, as he capably manages the delicate balancing act between style, comedy, and the grotesque.

#10: “Snatch” (2000)

Guy Ritchie is a master of the crime comedy, having directed the classic “Lock, Stock, and Two Smoking Barrels” as well as “Snatch.” And the latter is particularly acclaimed, even holding down the 103rd spot on IMDb’s Top Rated Movies list. There are so many things to enjoy about this dark comedy, including Ritchie’s impeccable stylistic flourishes, his penchant for writing memorable dialogue and characters, and Brad Pitt’s brilliant performance as “One Punch” Mickey O’Neil. And hey, so what if you sometimes can’t understand any heavily-accented dialogue? Throw on the subtitles, have a laugh, and enjoy one of the finest dark comedies ever.

#9: “The Wolf of Wall Street” (2013)

When you combine Martin Scorsese with Leonardo DiCaprio, you get art. This movie stars DiCaprio as real life stockbroker and scam artist Jordan Belfort, who spent 22 months in federal prison for fraud. The film is masterfully edited by longtime Scorsese collaborator Thelma Schoonmaker, resulting in a rapid-fire, erratic, drug-fueled good time. Think the last act of “Goodfellas,” only stretched to three volatile and surprisingly sprightly hours. It’s amazing that a story about Wall Street and stocks — and terrible fraud — can be so incredibly entertaining. Such are the incredible talents of its cast and crew.

#8: “After Hours” (1985)

Martin Scorsese really knows how to craft a dark comedy. Long before “The Wolf of Wall Street,” Scorsese showed his comedic chops with “After Hours.” The movie stars Griffin Dunne as the gentle Paul Hackett, a computer data entry worker who finds himself having the worst and most bizarre night of his life. It’s a total existential nightmare that is expertly edited by Schoonmaker and directed by Scorsese. While the movie was critically acclaimed and won the Best Director award at that year’s Cannes Film Festival, it never really took off and has since become one of Scorsese’s most underappreciated works of art.

#7: “Heathers” (1988)

The mid-to-late ‘80s were filled with popular teen comedies, many of them of the John Hughes variety. “Heathers” looked to change that. Winona Ryder stars as Veronica Sawyer, a popular high school student who meets and befriends the psychotic J.D. J.D. is the creepy, yet charismatic, outsider who has ulterior motives of his own - namely, killing popular, clique-y kids. Ryder and Christian Slater make for a dynamic duo, and the movie’s script touches on morbid concepts of teenage alienation and suicide, pre-meditated murder, and school violence. It takes a high degree of talent to make those themes funny, and “Heathers” pulls it off with confidence and dexterity.

#6: “Election” (1999)

“Election” is another marvelous high school satire, albeit a much less violent one. Matthew Broderick stars as Jim McAllister, a social studies teacher who looks to sabotage the student body election. Reese Witherspoon turns in arguably the greatest performance of her fine comedic career as Tracy Flick, the ambitious student who runs for school president. “Election” is not just another high school movie. It’s an intelligent and incisive look into the many aspects of high school life, including biased teachers, overambitious and obnoxious students, the indifferent student body, and administrative politics. Ironically enough, the movie is not particularly popular. But it is good.

#5: “Parasite” (2019)

There’s this little South Korean movie called “Parasite.” You may have heard of it. “Parasite” is writer-director Bong Joon-ho’s masterpiece, and it tells the story of a poor and conniving Korean family who infiltrate a wealthy clan as their servants. Bong Joon-ho uses this contained story as a microcosm to comment on wider social themes. “Parasite” made history by becoming the first South Korean movie to win the Palme d’Or and the first non-English film to win the Academy Award for Best Picture. It’s funny, it’s wildly unpredictable, and it has a lot to say about our modern social climate. In short, it’s a modern day masterpiece.

#4: “The Big Lebowski” (1998)

Coen brothers comedies are a bit of an acquired taste, and some prove largely divisive. That doesn’t seem to be the case with “The Big Lebowski.” This movie has become a giant cult favorite throughout the years, thanks in large part to the movie’s brilliant dialogue. That, and the memes. This movie is arguably the Coens’ most personable and unique, as it is filled with memorable lines, scenes, visual flourishes, and characters. Jeff Bridges is also out of this world good as legendary character The Dude. The Coens are masters at writing and directing, and the amazing star-studded ensemble cast does the rest. The result is pure cinematic magic.

#3: “In Bruges” (2008)

Martin McDonagh has proved himself one of the finest creators of dark comedy, having also crafted the likes of “Seven Psychopaths” and “Three Billboards Outside Ebbing, Missouri.” But perhaps his most capable blending of raw humanity and uproarious comedy is “In Bruges.” This movie sees the always-reliable Colin Farrell and Brendan Gleeson as two Irish hitmen who are hiding out in picturesque Bruges, Belgium and awaiting further orders from their boss, played by one of the best bad guy actors in the biz, Ralph Fiennes. The unique setting, sharp writing, and commendable performances all combine to create one of the dreariest and most depressingly hilarious comedies ever made. And we wouldn’t have it any other way.

#2: “Fargo” (1996)

While “The Big Lebowski” may be the Coens’ most popular comedy, “Fargo” is arguably their greatest original creation. It’s a brilliantly told story that effortlessly mixes elements of the crime genre with black comedy, endearing family dynamics, and glorious “Minnesota nice” accents. It’s just as funny as “The Big Lebowski,” but in a much more down-to-Earth way, deriving laughs from its regional idiosyncrasies. However, it is also far more violent, and it also takes itself far more seriously. Is “Fargo” — later adapted into a superb TV series — a funny crime drama, or a comedy filled with murder, kidnapping, and despicable criminals? We don’t really know, but that’s why the Coen brothers are such masters of the film medium.

Before we unveil our top pick, here are a few honorable mentions.

“Observe and Report” (2009)
“Super” (2010)
“Death at a Funeral” (2007)
“The Trouble with Harry” (1955)
“In the Loop” (2009)

#1: “Dr. Strangelove” (1964)

And finally we come to the granddaddy of black comedies - Stanley Kubrick’s seminal masterpiece “Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb.” Kubrick made many iconic films throughout his illustrious career, but none were as funny or as fiercely sardonic as “Dr. Strangelove.” Released just fifteen months after the Cuban Missile Crisis, this movie lampoons many aspects of the Cold War, including the missile gap, elaborate fallout shelter networks, and mutually assured destruction. It’s certainly a product of its time, but like most pieces of art, this supreme satire can be enjoyed at any time by anyone.
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