There are spoilers forward for every entry!

Folks go to the flicks for all kinds of causes. To cry, be scared, be immersed in a strong story, and, in fact, to snicker. Comedies, by their very nature, are movies meant to entertain. They search to make audiences smile and cackle their hearts out, and probably the most formidable ones would possibly even throw a potently dramatic story within the combine for the proper steadiness between amusing and thought-provoking.

Then, there are comedy films which can be completely miserable—not simply unhappy or poignant however emotionally crushing movies that, positive, provide plenty of laughter and leisure however in the end depart audiences feeling fairly terrible. It is exhausting to make a comedy film miserable and nonetheless have or not it’s satisfying, however the movies which have achieved such a feat all through the years are among the many style’s finest. These are probably the most miserable comedy films that may depart the viewers with a hole sensation after the laughing is over.

10

‘Marley & Me’ (2008)

Directed by David Frankel

Marley & Me is likely one of the finest canine films ever a few household that learns necessary life classes from their lovely however naughty and neurotic canine. It is not a very inventive movie, nor does it do something groundbreaking comedically or dramatically, but it surely hits all of the emotional beats that it goals for with ease. Greater than something, folks keep in mind Marley & Me for its heartbreaking ending.

The third act sees the ageing Labrador retriever Marley get a lethal intestinal dysfunction. After two shut encounters with loss of life, the household has to euthanize him with John (Owen Wilson) by his aspect. It is an awfully unhappy notice to finish the film on, which each viewers member who has ever owned a pet is certain to have the ability to empathize with. For a comedy that is in any other case fairly upbeat, this ending single-handedly makes it one of many saddest of the 2000s.

9

‘Could December’ (2023)

Directed by Todd Haynes

Todd Haynes is the religious and stylistic successor to the melodrama filmmakers of Classical Hollywood, as he has always proved together with his phenomenal physique of labor. However his newest work, Could December, finds a very recent steadiness between melodrama and darkish comedy. Impressed by a real story, it is set twenty years after a infamous tabloid romance between a trainer (Julianne Moore) and her teenage pupil (Charles Melton) shook the nation. The couple, nonetheless married, buckles beneath stress when an actress (Natalie Portman) arrives at their residence to do analysis for a movie about their story.

There are actually hints of darkish humor and amusingly weird moments in Could December. Nonetheless, greater than anything, it is a deeply disturbing and much more deeply unhappy psychological drama that examines the character and results of grooming, tabloid journalism, and actors whose “course of” has left them out of contact with actuality. Moore and Portman’s characters are one of the fascinating feminine duos of any 2020s film, but it surely’s Charles Melton’s gut-wrenchingly harmless efficiency and his brilliantly written character that actually make Could December miserable by all accounts.

8

‘The Banshees of Inisherin’ (2022)

Directed by Martin McDonagh

Regardless that he is largely devoted to writing theater, Martin McDonagh has additionally proved on a number of events to be top-of-the-line filmmakers that the style of darkish comedy at present has. Most lately, he cemented that popularity with The Banshees of Inisherin, a interval dramedy about two lifelong mates (Colin Farrell and Brendan Gleeson) who discover themselves at an deadlock when one among them abruptly ends their relationship.

What begins as a comparatively lighthearted comedy begins turning sadder, extra bitter, and darker because the lead characters’ relationship retains deteriorating to always stunning levels. All of it culminates in a brilliantly sudden ending that is equal elements tragically humorous and profoundly unhappy, with the 2 most important characters now feeling extra like bitter enemies than mates. There’s extra loss of life, heartbreak, and loneliness in The Banshees of Inisherin than the overwhelming majority of comedies are in a position to deal with, and McDonagh writes and directs all of it to perfection.

7

‘It is Such a Stunning Day’ (2012)

Directed by Don Hertzfeldt

A function model of American indie animator and filmmaker Don Hertzfeldt‘s brief movie collection, It is Such a Stunning Day is nothing in need of top-of-the-line animated films of the twenty first century. It is about Invoice, a stick determine man who struggles to place collectively his shattered psyche. Stunning in its visible simplicity and shocking in how a lot emotional and thematic content material it is in a position to pack in just a bit over an hour of runtime, Hertzfeldt’s function masterpiece is a must-see for animation followers.

Because it occurs, It is Such a Stunning Day can be one of many saddest animated films ever made. There’s a number of darkish comedy that is assured to make viewers snicker, and the film is in the end fairly uplifting. Nevertheless, the philosophical depth and emotionally devastating nature of the narrative are more likely to depart folks with a miserable existential disaster. The truth that such a small and easy film is ready to do all that in simply 62 minutes is greater than spectacular.

It is Such a Stunning Day is at present not out there to stream, hire, or buy within the U.S.

6

‘Songs from the Second Flooring’ (2000)

Directed by Roy Andersson

Recognized for his melancholic naturalism and pleasant absurdist humor, Swedish black comedy director Roy Andersson has made a number of distinctive movies all through his profession, however many individuals’s favourite is Songs from the Second Flooring. It is a movie poem a few monumental site visitors jam that serves because the backdrop for the lives of the inhabitants of a Swedish metropolis.

There aren’t many films that handle to be as outrageously hilarious and philosophically profound as Songs from the Second Flooring, however that is simply the form of artist Roy Andersson is. Among the finest worldwide movies of the 2000s, this extensively regarded gem has vignettes that by no means stop to be surreal and absurd, including to a better complete that evaluates the fashionable world’s lack of spirituality in all of its totally different façets. It is hysterical, overwhelmingly unhappy stuff.

Watch on Criterion

5

‘In Bruges’ (2008)

Directed by Martin McDonagh

From the very begin of his movie profession, in his debut of In Bruges, Martin McDonagh proved how delightfully nicely his playwright expertise transferred to the massive display. It is about two hitmen (Farrell and Gleeson) who, after a job gone fallacious, should journey to Bruges, Belgium, to await additional orders from their ruthless boss (Ralph Fiennes). Hilariously absurd hijinks and humor that is certain to offend each demographic which may watch the movie ensue.

The wild and one-of-a-kind In Bruges remains to be the darkest and most outrageous instance of McDonagh’s humorousness on the massive display, and it is all the higher for it. It is a gloomy film with plenty of violence, ethical depravity, and one of the hilarious deaths in film historical past, but it surely’s additionally undeniably miserable. The deaths within the movie are distressing, and so is the awful ending. The principle character’s ethical quandaries after having by accident killed a baby are actually harrowing.

4

‘Three Billboards Exterior Ebbing, Missouri’ (2017)

Directed by Martin McDonagh

Sure, Martin McDonagh’s films are this hilariously miserable. To this present day, nonetheless, his saddest comedy stays the brutal Three Billboards Exterior Ebbing, Missouri. It is a few mom who personally challenges the native authorities to resolve her daughter’s homicide once they fail to catch the offender. Frances McDormand is larger-than-life within the masterful lead efficiency that gave her a second Greatest Actress Oscar.

One of many darkest thrillers of the 2010s, Three Billboards is a strong character research concerning the nature of justice, the elusiveness of forgiveness, and the way far a mom’s love — and anger — can go. All of it seems like deeply touching, romantic stuff, however the film is as darkly humorous and irresistibly miserable as one can count on from any Martin McDonagh movie at this level. Each character within the film is grieving and struggling in a singular and deeply humane method, and issues aren’t simply magically solved by the point the credit roll. There’s hope and some extent of happiness, however struggling would not simply disappear.

3

‘Happiness’ (1998)

Directed by Todd Solondz

Well-known for simply how twistedly disturbing it’s for a comedy, Happiness is likely one of the most infamous movies of the late ’90s. It is concerning the lives of a number of people intertwining as they go about their days in distinctive methods, participating in acts that correct society would discover reproachable of their determined seek for connection. Sharp, wicked, and taboo, it is one among the boldest films which have ever been courageous sufficient to label themselves as a comedy.

Happiness is commonly grimly humorous, positive, but it surely’s additionally one of the miserable films of the ’90s. Launched unrated after it acquired an NC-17 ranking, the film dives deep into the psyche of some characters whose morals are lower than well-aligned. Most significantly, what makes the movie so controversial is its portrayal of pedophilia within the character performed brilliantly by Dylan Baker. Happiness is a comedy that requires an open thoughts, and it actually will not depart viewers feeling good, but it surely’s a really rewarding look ahead to these with the abdomen for it.

Happiness is at present not out there to stream, hire, or buy within the U.S.

2

‘Bare’ (1993)

Directed by Mike Leigh

The highly-awarded British auteur Mike Leigh has directed many distinctive films all through his profession, maybe chief amongst them being the very darkish dramedy Bare. It stars an exceptional David Thewlis as an unemployed man from Manchester who flees to London after he abused a woman. There, he vents his rage on unsuspecting strangers as he embarks on a nocturnal odyssey.

Bare proves {that a} movie can have a protagonist that is a completely deplorable excuse for a human being and nonetheless be not simply compelling, however even surprisingly simple to attach with. Leigh’s portrayal of nihilism and crippling existential dread is deeply miserable, as a lot as it’s past unsettling to should observe this horrible man for a bit over two hours. Bare is fascinating and stuffed with efficient scornful humor, but it surely’s additionally devastatingly unhappy.

1

‘Anomalisa’ (2015)

Directed by Charlie Kaufman and Duke Johnson

Charlie Kaufman is probably probably the most gifted screenwriter working in Hollywood as we speak. Comparatively lately, he made the leap to the director’s chair, proving that there is nothing that his twistedly comedic and philosophically good inventive thoughts cannot do. His second film was the stop-motion surrealist masterpiece Anomalisa, a few man (David Thewlis) crippled by the mundanity of his life and unable to type connections. Sooner or later, his life adjustments when he meets the attention-grabbing Lisa (Jennifer Jason Leigh).

Like just about all of Kaufman’s movies, this darkish comedy has a distinctly darkish humorousness that in some way nonetheless elicits plenty of laughter; nonetheless, it is also arguably his most miserable movie. With Kaufman and Duke Johnson‘s energetic course and top-of-the-line screenplays of any animated film, Anomalisa is a shattering examination of ageing, relationships, and the determined want for human connection. It might be humorous, however the principle emotion that viewers will likely be feeling by the point the credit roll is impossible-to-contain disappointment and existential dread.

NEXT:The Saddest Coming-of-Age Motion pictures, Ranked