WatchMojo

Login Now!

OR   Sign in with Google   Sign in with Facebook
advertisememt

Top 30 Best Dark Comedies of All Time

Top 30 Best Dark Comedies of All Time
VOICE OVER: Rebecca Brayton WRITTEN BY: Beca Dalimonte, Nathan Sharp
Laughter meets the macabre in our countdown of the best dark comedies ever made. From satirical masterpieces to pitch-black humor, these films push boundaries and tickle our funny bones in unexpected ways. Join us as we explore the finest examples of comedy's darker side, featuring beloved classics and hidden gems alike. Our list includes iconic films like "Dr. Strangelove," "Fargo," and "The Big Lebowski," as well as more recent hits like "Parasite" and "The Death of Stalin." Whether you're a fan of biting satire, absurdist humor, or just enjoy a good laugh with a twist, this countdown has something for everyone. Who is your favorite superhero? Let us know in the comments.
Top 30 Best Dark Comedies of All Time


Welcome to WatchMojo, and today we’re counting down our picks for the best comedies with unconventionally dark subject matter and a biting edge.

#30: “The Menu” (2022)

Set in the exclusive restaurant of famed chef Julian Slowik[a], “The Menu” slowly builds on an atmosphere of awkwardly funny discomfort before revealing its characters’ horrifying intentions. Margot, played by Anya Taylor-Joy, is at the center of it all, the sole innocent among an island of morally bankrupt elite and corrupt chefs. The 2022 film was a surprise hit with audiences, quickly becoming Searchlight’s biggest opening at the box office in fourteen years. And it’s not hard to see why. “The Menu’s” pitch-perfect cast, strikingly original plot, satire of the uber rich, and the intriguing world of fine dining all added up to a surefire recipe for success.

#29: “Beetlejuice” (1988)

A movie so good, we’ll sing its praises thrice. “Beetlejuice” may not be your typical dark comedy, injecting complex practical effects and absurd fantasy into the world of an ordinary family, but that’s exactly what makes it so special. Despite being released over three decades ago, “Beetlejuice” worms its way into every single Halloween season and, after the release of its sequel, “Beetlejuice Beetlejuice,” it’s obvious it’s here to stay. But you won’t hear us complaining! From beginning to end, every frame of the film leaves a lasting impression. The costuming, the performances, the music - it’s all so instantly iconic, and so singularly true to itself.

#28: “The Producers” (1967)

Dark comedy and controversy go hand in hand, but few dark comedies have been quite as controversial as “The Producers.” The film tackles the challenging topic of Nazism[b] through the lens of a celebratory play penned by a pair of con artists. As with “To Be or Not to Be” before it, and “Jojo Rabbit” after it, critics and audiences were initially mixed on how the film handled such a serious subject. But, as time went on, people began to accept the work for the brilliant piece of satire it is. “The Producers” became a cult classic, and even entered the National Film Registry nearly thirty years after its release.


#27: “In the Loop” (2009)

Prior to creating the Emmy-award winning HBO comedy, “Veep,” Armando Iannucci[c] dipped his toes into the messy world of American politics with “In the Loop.” Set during a time when the UK and US are considering military intervention in the Middle East, the film is, at times, realistically bleak, and, at others, absurdly funny, with endlessly quotable dialogue. …And did we mention it features a pre-“Doctor Who” Peter Capaldi, and post-“Sopranos” James Gandolfini? It’s a must-watch political satire even - or, perhaps, especially - for those disenchanted with modern politics.

#26: “Little Miss Sunshine” (2006)

In spite of its cheery title, “Little Miss Sunshine” delves into some pretty dark topics. At the film’s start we learn that Steve Carell’s character, Frank, has recently tried to take his own life. The family eventually experiences a devastating loss while on the road and, even Dwayne, played by a young Paul Dano, is forced to confront a difficult truth about his future. Fortunately, it’s not all doom and gloom. The road trip is also filled with plenty of laughs, and ends with a heartwarming performance subtly criticizing child beauty competitions which were quite popular at the time. The darkly comedic crowd-pleaser was such a hit that it was nominated for Best Picture at the Academy Awards, and landed writer Michael Arndt[d] an Oscar for Best Original Screenplay.

#25: “Harold and Maude” (1971)

This 1971 film isn’t just a dark comedy, it’s a dark romantic comedy, with a shockingly unconventional romance at its center. Bud Cort and Ruth Gordon star as the titular Harold and Maude, who meet each other at the funeral of a person neither of them knew. Ironically, Harold, the younger of the two, is obsessed with death, while the seventy-nine-year-old Maude still entertains a zest for life. Their differences are the jumping off point not only for the film’s quirky comedy, but its beautifully bittersweet drama as well. If you’re a fan of atypical love stories with a dash of humor, “Harold and Maude” is not to be missed!

#24: “Sorry to Bother You” (2018)

Boots Riley is a quadruple threat, entertaining success as a rapper, producer, screenwriter, and director. In 2018, he released his first feature film, “Sorry to Bother You,” which was inspired by his former work as a telemarketer. The film utilized surreal sci-fi elements that occasionally pushed its narrative into horror territory, all while still discussing real, human issues. This unique approach, paired with memorable costuming and piercing satire, made “Sorry to Bother You” one of the most inventive films of that year - or any year. It confronts racism head-on in a way that is also distinctly anti-capitalist, but is nonetheless an entertaining must watch for any fan of the dark comedy genre. Just make sure to go in blind!

#23: “Inglourious Basterds” (2009)

This Best Picture nominee is often thought of as a film in the war and action genres, with thrilling suspense and surprising drama. But, like all of Quentin Tarantino’s films, it’s also often darkly humorous. Dialogue is exchanged by the film’s actors with great finesse, perfectly orchestrated to create an appropriate level of levity against the horrifying backdrop of 1940’s Germany. It’s part of what makes “Inglourious Basterds” so great, and worthy of returning back to again and again. If you haven’t seen it yet - what are you waiting for? “Pulp Fiction” may have had a bigger impact on pop culture, but “Basterds” may be Tarantino’s greatest masterpiece.


#22: “The Favourite” (2018)

In 2023, Emma Stone and Yorgos Lanthimos[e] surprised audiences with “Poor Things,” an irreverent and profane fairy tale that stumbled its way into several of that year’s major award ceremonies. The film came five years after the actress and director’s first collaboration, “The Favourite,” which followed a more traditional narrative structure but was no less audacious. Also starring heavy hitters Olivia Colman and Rachel Weisz, “The Favourite” quickly became a favorite of critics and audiences alike. As with its successor, it earned a coveted Best Picture nomination, and even led to Olivia Colman receiving her first Oscar in the Best Actress category.


#21: “Network” (1976)

This 1976 satire’s cable TV setting is quickly becoming dated but its shocking commentary on the American entertainment industry remains timeless. Directed by Sidney Lumet, who also gave us classics like “12 Angry Men” and “Dog Day Afternoon,” “Network” is a masterclass in screenwriting. Viewers laugh and cringe in equal measure, as the tense atmosphere behind the scenes of UBS Evening News continues to ramp up towards a shockingly bleak crescendo. At the center of it all, English-Australian actor Peter Finch is at the top of his game as Howard Beale, a role which would come to be known as his last and, for many, his best.


#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, (xref) 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.


#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.


How many of these dark comedies have you seen? Let us know in the comments!

Comments
advertisememt