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Image via Focus Features
There are spoilers ahead for each entry!
People go to the movies for all sorts of reasons. To cry, be scared, be immersed in a powerful story, and, of course, to laugh. Comedies, by their very nature, are films meant to entertain. They seek to make audiences smile and cackle their hearts out, and the most ambitious ones might even throw a potently dramatic story in the mix for the perfect balance between amusing and thought-provoking.
Then, there are comedy movies that are absolutely depressing—not just sad or poignant but emotionally crushing films that, sure, offer lots of laughter and entertainment but ultimately leave audiences feeling quite awful. It's hard to make a comedy movie depressing and still have it be satisfying, but the films that have achieved such a feat throughout the years are among the genre's best. These are the most depressing comedy movies that will leave the audience with a hollow sensation after the laughing is over.
10 'Marley & Me' (2008)
Directed by David Frankel
Image via 20th Century Studios
Marley & Me is one of the best dog movies ever about a family that learns important life lessons from their adorable but naughty and neurotic dog. It's not a particularly creative film, nor does it do anything groundbreaking comedically or dramatically, but it hits all the emotional beats that it aims for with ease. More than anything, people remember Marley & Me for its heartbreaking ending.
The third act sees the aging Labrador retriever Marley get a deadly intestinal disorder. After two close encounters with death, the family has to euthanize him with John (Owen Wilson) by his side. It's an awfully sad note to end the movie on, which every audience member who has ever owned a pet is sure to be able to empathize with. For a comedy that's otherwise pretty upbeat, this ending single-handedly makes it one of the saddest of the 2000s.
Marley & Me
Release Date December 25, 2008
Runtime 115 Minutes
Writers Don Roos , Scott Frank
9 'May December' (2023)
Directed by Todd Haynes
Image via Netflix
Todd Haynes is the spiritual and stylistic successor to the melodrama filmmakers of Classical Hollywood, as he has constantly proved with his phenomenal body of work. But his latest work, May December, finds a particularly fresh balance between melodrama and dark comedy. Inspired by a true story, it's set twenty years after a notorious tabloid romance between a teacher (Julianne Moore) and her teenage student (Charles Melton) shook the nation. The couple, still married, buckles under pressure when an actress (Natalie Portman) arrives at their home to do research for a film about their story.
There are certainly hints of dark humor and amusingly bizarre moments in May December. Still, more than anything else, it's a deeply disturbing and even more deeply sad psychological drama that examines the nature and effects of grooming, tabloid journalism, and actors whose "process" has left them out of touch with reality. Moore and Portman's characters are one of the most fascinating female duos of any 2020s movie, but it's Charles Melton's gut-wrenchingly innocent performance and his brilliantly written character that really make May December depressing by all accounts.
Release Date December 1, 2023
Runtime 113 Minutes
Writers Samy Burch , Alex Mechanik
8 'The Banshees of Inisherin' (2022)
Directed by Martin McDonagh
Image via Searchlight Pictures
Even though he's mostly dedicated to writing theater, Martin McDonagh has also proved on several occasions to be one of the best filmmakers that the genre of dark comedy currently has. Most recently, he cemented that reputation with The Banshees of Inisherin, a period dramedy about two lifelong friends (Colin Farrell and Brendan Gleeson) who find themselves at an impasse when one of them abruptly ends their relationship.
What starts as a relatively lighthearted comedy starts turning sadder, more sour, and darker as the lead characters' relationship keeps deteriorating to constantly shocking degrees. It all culminates in a brilliantly sudden ending that's equal parts tragically funny and profoundly sad, with the two main characters now feeling more like bitter enemies than friends. There's more death, heartbreak, and loneliness in The Banshees of Inisherin than the vast majority of comedies are able to handle, and McDonagh writes and directs it all to perfection.
The Banshees of Inisherin
Release Date October 21, 2022
Runtime 109 minutes
7 'It's Such a Beautiful Day' (2012)
Directed by Don Hertzfeldt
Image via Bitter Films
A feature version of American indie animator and filmmaker Don Hertzfeldt's short film series, It's Such a Beautiful Day is nothing short of one of the best animated movies of the 21st century. It's about Bill, a stick figure man who struggles to put together his shattered psyche. Beautiful in its visual simplicity and surprising in how much emotional and thematic content it's able to pack in just a little over an hour of runtime, Hertzfeldt's feature masterpiece is a must-see for animation fans.
As it happens, It's Such a Beautiful Day is also one of the saddest animated movies ever made. There's a lot of dark comedy that's guaranteed to make viewers laugh, and the movie is ultimately quite uplifting. However, the philosophical depth and emotionally devastating nature of the narrative are likely to leave people with a depressing existential crisis. The fact that such a small and simple movie is able to do all that in just 62 minutes is more than impressive.
It's Such A Beautiful Day
Release Date August 24, 2012
Cast Don Hertzfeldt
Runtime 62 Minutes
Writers Don Hertzfeldt
It's Such a Beautiful Day is currently not available to stream, rent, or purchase in the U.S.
6 'Songs from the Second Floor' (2000)
Directed by Roy Andersson
Image via Canal+
Known for his melancholic naturalism and delightful absurdist humor, Swedish black comedy director Roy Andersson has made several exceptional films throughout his career, but many people's favorite is Songs from the Second Floor. It's a film poem about a monumental traffic jam that serves as the backdrop for the lives of the inhabitants of a Swedish city.
There aren't many movies that manage to be as outrageously hilarious and philosophically profound as Songs from the Second Floor, but that's just the kind of artist Roy Andersson is. One of the best international films of the 2000s, this widely regarded gem has vignettes that never cease to be surreal and absurd, adding to a greater whole that evaluates the modern world's loss of spirituality in all of its different façets. It's hysterical, overwhelmingly sad stuff.
5 'In Bruges' (2008)
Directed by Martin McDonagh
Image via Focus Features
From the very start of his film career, in his debut of In Bruges, Martin McDonagh proved how delightfully well his playwright skills transferred to the big screen. It's about two hitmen (Farrell and Gleeson) who, after a job gone wrong, have to travel to Bruges, Belgium, to await further orders from their ruthless boss (Ralph Fiennes). Hilariously absurd hijinks and humor that's bound to offend every demographic that might watch the film ensue.
The wild and one-of-a-kind In Bruges is still the darkest and most outrageous example of McDonagh's sense of humor on the big screen, and it's all the better for it. It's a gloomy movie with lots of violence, moral depravity, and one of the most hilarious deaths in movie history, but it's also undeniably depressing. The deaths in the film are distressing, and so is the bleak ending. The main character's moral quandaries after having accidentally killed a child are certainly harrowing.
In Bruges
Release Date February 8, 2008
Runtime 107minutes
4 'Three Billboards Outside Ebbing, Missouri' (2017)
Directed by Martin McDonagh
Image via Fox Searchlight
Yes, Martin McDonagh's movies are this hilariously depressing. To this day, however, his saddest comedy remains the brutal Three Billboards Outside Ebbing, Missouri. It's about a mother who personally challenges the local authorities to solve her daughter's murder when they fail to catch the culprit. Frances McDormand is larger-than-life in the masterful lead performance that gave her a second Best Actress Oscar.
One of the darkest thrillers of the 2010s, Three Billboards is a powerful character study about the nature of justice, the elusiveness of forgiveness, and how far a mother's love — and anger — can go. It all sounds like deeply touching, romantic stuff, but the movie is as darkly funny and irresistibly depressing as one can expect from any Martin McDonagh film at this point. Every character in the movie is grieving and suffering in a singular and deeply humane way, and things aren't just magically solved by the time the credits roll. There's hope and some degree of happiness, but suffering doesn't just disappear.
Release Date December 1, 2017
Runtime 115 minutes
3 'Happiness' (1998)
Directed by Todd Solondz
Image via Good Machine
Famous for just how twistedly disturbing it is for a comedy, Happiness is one of the most notorious films of the late '90s. It's about the lives of several individuals intertwining as they go about their days in unique ways, engaging in acts that proper society would find reproachable in their desperate search for connection. Sharp, depraved, and taboo, it's one of the boldest movies that have ever been brave enough to label themselves as a comedy.
Happiness is a comedy that requires an open mind, and it certainly won't leave viewers feeling good, but it's a very rewarding watch for those with the stomach for it.
Happiness is often grimly funny, sure, but it's also one of the most depressing movies of the '90s. Released unrated after it received an NC-17 rating, the movie dives deep into the psyche of a few characters whose morals are less than well-aligned. Most particularly, what makes the film so controversial is its portrayal of pedophilia in the character played brilliantly by Dylan Baker. Happiness is a comedy that requires an open mind, and it certainly won't leave viewers feeling good, but it's a very rewarding watch for those with the stomach for it.
Happiness is currently not available to stream, rent, or purchase in the U.S.
2 'Naked' (1993)
Directed by Mike Leigh
Image via First Independent Films
The highly-awarded British auteur Mike Leigh has directed many exceptional movies throughout his career, perhaps chief among them being the very dark dramedy Naked. It stars a phenomenal David Thewlis as an unemployed man from Manchester who flees to London after he abused a girl. There, he vents his rage on unsuspecting strangers as he embarks on a nocturnal odyssey.
Naked proves that a film can have a protagonist that's an absolutely deplorable excuse for a human being and still be not just compelling, but even surprisingly easy to connect with. Leigh's portrayal of nihilism and crippling existential dread is deeply depressing, as much as it is beyond unsettling to have to follow this horrible man for a bit over two hours. Naked is fascinating and full of effective scornful humor, but it's also devastatingly sad.
Naked
Release Date September 14, 1993
Runtime 131 minutes
Writers Marlon Wayans , Rick Alvarez
1 'Anomalisa' (2015)
Directed by Charlie Kaufman and Duke Johnson
Image via Paramount Pictures
Charlie Kaufman is perhaps the most talented screenwriter working in Hollywood today. Relatively recently, he made the jump to the director's chair, proving that there's nothing that his twistedly comedic and philosophically brilliant creative mind can't do. His second movie was the stop-motion surrealist masterpiece Anomalisa, about a man (David Thewlis) crippled by the mundanity of his life and unable to form connections. One day, his life changes when he meets the interesting Lisa (Jennifer Jason Leigh).
Like pretty much all of Kaufman's films, this dark comedy has a distinctly dark sense of humor that somehow still elicits lots of laughter; still, it's also arguably his most depressing film. With Kaufman and Duke Johnson's lively direction and one of the best screenplays of any animated movie, Anomalisa is a shattering examination of aging, relationships, and the desperate need for human connection. It may be funny, but the main emotion that viewers will be feeling by the time the credits roll is impossible-to-contain sadness and existential dread.
Anomalisa
Release Date December 13, 2015
Runtime 1h 30m
English (US) ·