Great Dark Comedies - No not stuff like Barbershop or Madea

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I'm gonna nominate this early Gen-X classic, River's Edge (1986) (My other top pick would be Fargo, which someone already mentioned. Third place would go to To Die For, with Nicole Kidman and Matt Dillon in one of his most likeable roles)


This has it all. A dark tale, based loosely on a real incident in California in the early 80's, in which a high schooler murdered a classmate for no real reason whatsoever, and his classmates all made treks to look at the body but didn't report it. The Baby Boomers were confounded by the real news item when it happened; it was the first hint that they had raised apathetic, desensitized monsters and it raised alarm bells.

We apathetic desensitized monsters generally loved the flick, although younger people have reported to me that they find it "corny". I guess you had to be there...

Crispin Glover at his most unhinged and Dennis Hopper (on the comeback trail in 1986 after a lost decade) provide many of the overt laughs, but there was a sinister dark humor in almost everything, from the dialog to the cinematography (which was very low-budget; this was an indie film) This was also one of Keanu Reeves' first films. It was Ione Skye Leitch's debut.

This Tim Burton film is dark enough that nobody in their right mind would call it a comedy, although it is darkly funny enough in overt ways that it can't quite be called serious; it walked a fine line, and it tells a compelling story, rich with detail right down to the flabbergasted Baby Boomer high school teacher, who bored his students to death with claims of how the Baby Boom ended the Vietnam War, and can't wrap his head around this seemingly brain-dead and emotionless new generation. The younger, elementary school Gen-X'ers are portrayed as downright psychotic. It conveys a sense of suburbia cracking up, and things taking a real turn for the worse.

If you caught this at the right time or the right age, you know why I love this film. If you come at it the wrong way, you might just find too amped-up and melodramatic. But I see those characteristics as benefits to the film.
 
Another Todd Solondnz film: Storytelling. Doesn't leave you feeling as skeevy as Happiness, but maybe not as good. Welcome to the Dollhouse is another TS film I recommend.
I've seen all of Todd's films sans Fear, Anxiety, and Depression and Life During Wartime, and I liked all of them.

Dark Horse is my personal favorite

Pink Flamingos.

Is that too dark?

Nope. Go as pitch black as you possibly can.

Also I have it on DVD
 
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A few others:

Dr. Caligari (1989).


There's another movie similar to this with the same kind of "eccentric" acting style like Singapore Sling which weirdly came out around the same time.


Not a big fan of it but perhaps others would enjoy it? The filmmakers behind Dr. Caligari made similar themed porno films like Cafe Flesh.

The Greasy Strangler.


Sweet Movie.


Not sure if "dark comedy" is a good description but it has that element along with surrealistic violence.

Rubber.


Death Bed: the Bed that Eats.


And of course Vampire's Kiss.

 
'Mr Lonely' is pretty grim and hilarious in equal measure. It takes a while to get going, but the combination of the world's worst celebrity impersonators putting on the world's worst show followed by the devastation when the show goes wrong is worth sitting through it. The subplot with Werner Herzog as a missionary priest whose nuns experience a miracle that goes wrong at the worst moment is pretty great too.

'I'm your number one fan' is a documentary about stalkers. It's disturbing stuff given that the people interviewed are very, very ill but you can't not laugh at a middle-aged blue haired woman having a screaming temper tantrum when someone suggests the radio dj she thinks she's married to is gay. The less said about her mid-morning audio-induced orgasm the better.
 
Idle Hands is a favorite black comedy of mine. That's the one where Devon Sawa has an evil hand which he chops off that terrorizes people and kills his two friends, one of them being Seth Green.
Also Jessica Alba is in it because she was a hit at the time. Also tons of pot. It had a good soundtrack too.
 
Can highly recommend these, though the reviews will be more persuasive since everybody else agrees too.


 
Lots of great suggestions in this thread. I'd like to add an early short by Ari Aster (director of Hereditary and Midsommar): The Strange Thing About The Johnsons. While I've never seen it officially described as a dark comedy, and there are definitely people out there claiming it's an entirely earnest portrait of a difficult family situation, I refuse to believe that Aster didn't intend it to be wickedly hilarious.
 
Death at a Funeral directed by Frank Oz. Two brothers welcome their family and friends to bid farewell to their father. But a few surreal incidents and the difficult relationships between the members of the family (added to the dead's unsavory past) will make for and unforgettable funeral.

Tucker and Dale Vs Evil: Tucker and Dale are two hillbillies who just just bought the fishing cabin of their dreams, and plan to spend a whole weekend restoring and refurbishing it. Not far from the cabin, a group of college students are camping in the forest and sadly, college students who camp in forests are apparently prone to misunderstandings.
 
Delicatessen by Jean-Pierre Jeunet (of Amelie fame) and Marc Caro. It's about a post-apocalyptic society and cannibalism and a fucked up apartment building where it happens.

Man Bites Dog by probably nobody you ever heard of, a Belgian movie which is a mock documentary about a serial killer who takes the documentary team along with him on his adventures. It's written by Rémy Belvaux who is otherwise mainly known for throwing a pie at Bill Gates and committing suicide (unrelated events).

Natural Born Killers. This more or less speaks for itself.

Shallow Grave, directed by Danny Boyle (Trainspotting). This is a very good and underrated movie with very early performances by Ewan McGregor and Christopher Eccleston as well as Kerry Fox, all playing genuinely terrible people. A new flatmate shows up, promptly ODs on drugs, and leaves behind a bag of money. They immediately do the wrong thing and things get worse and worse and worse.

Trainspotting itself of course.

Someone also recommended The Royal Tenenbaums and I do, too. This is actually more light than dark even though it has suicide and other depressing stuff in it, although the suicide attempt actually leads into one of the funniest scenes.

The Devil's Rejects. This is usually billed as a horror movie but a lot of it is actually quite funny, although the humor is often drawn from Tarantino-like constant references to the trashy exploitation films Rob Zombie loves. Its predecessor House of 1,000 Corpses may also be worth it if you like this kind of thing, although it isn't as broadly appealing as Devil's Rejects.

Also comedy horror, From Dusk Till Dawn, directed by Robert Rodriguez and written by Quentin Tarantino. It's more an action comedy with horror elements than a truly black comedy.

Others that are minor and and I find it hard to recommend wholeheartedly that are more dark than comedy.

Love Liza, a Philip Seymour Hoffman vehicle about a guy who starts huffing gasoline after his girlfriend commits suicide and he can't bring himself to read her suicide letter. Things get worse and worse and worse. This may be the single most depressing movie I've ever seen and the comedy is sparse and dry as a bone.

Permanent Midnight, another dryly comic drug drama starring Ben Stiller as heroin addicted screenwriter Jerry Stahl.
 
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