I enjoyed both of these. I honestly thought Ready or Not (2019, starring Samara Weaving) would qualify here, too.
A few I wanted to add, for various flavors of dark comedies, although most of them are very blurred with other categories.
First, the Cornetto Trilogy, ie Shaun of the Dead, Hot Fuzz, and The World’s End.
All are dark comedies of different flavors, although compared to many in this thread, they lean more heavily into the comedy than the dark. That being said, they also have their own unspeakably dark moments, and since each are blended with different elements, at least one is generally likely to speak to you more than the others.
The last are more of an edge case than the above. That would be the 80s classic scifi/horror/satire “The Stuff”. It, like the similarly edge case of “They Live” are horror movies that satirize our society, in an incredibly dark way, that makes you go more “ha ha… ouch.” They aren’t comedies in the sense of some of the others listed, but I think they overlap enough to be at least mentioned.
A mix of highbrow and lowbrow:
Sunset Blvd. (1950)
A Bucket of Blood (1959)
The Skeleton of Mrs. Morales (1960)
Viridiana (1961)
The Graceful Brute (1962)
Faster Pussycat! Kill! Kill! (1965)
No Way to Treat a Lady (1968)
Beyond the Valley of the Dolls (1970)
The Abominable Dr. Phibes (1971)
Cry Uncle (1971)
Pretty Maids All in a Row (1971)
Andy Warhol’s Frankenstein (1973 – but ONLY in 3D!)
Theater of Blood (1973)
Andy Warhol’s Dracula (1974)
Going Places (1974)
Monty Python and the Holy Grail (1975)
Network (1976)
Andy Warhol’s Bad (1977)
Winter Kills (1979)
An American Werewolf in London (1981)
The Fourth Man (1983)
From Beyond (1986)
Evil Dead II (1987)
Brain Damage (1988)
Marquis (1989)
Frankenhooker (1990)
Dead Alive a.k.a. Braindead (1992)
Innocent Blood (1992)
Thursday (1998)
The Woman Chaser (1999)
Revengers Tragedy (2002)
The Big Empty (2003)
Kick-Ass (2010)
The Gentlemen (2019)
I’ve never looked at an ice cream truck the same way since.
I adore this movie! Tuckman Marsh! Tuchmna Marsh! I laughed so hard at the final scene with J. K. Simmons. I’m always happy when “pretty boy” leading men play ridiculous characters, and both Brad Pitt and George Clooney are ridiculous in this film.
I’d recommend Happy Death Day 2U. The original was straight horror, despite the Groundhog Day hook. The sequel comes off more as a dark comedy.
The End of the F***ing World centers on a psychopath and his true love. Two seasons.
You’re the Worst centers on two toxic, self-centred people who fall in love. Five seasons.
What, nobody’s mentioned any John Waters movies yet? Okay, I will:
Female Trouble and Desperate Living are dark, violent, and fucking hilarious. Also Pink Flamingos and Polyester. I like JW’s outrageous earlier movies much better than his more recent, more mnainstream stuff. And, leaving the esteemed Mr. W’s ouevre for now, we’ve got: Spun, a funny, dark-edged, realistic comedy/drama following the misadventures of a group of speedfreaks, Arnold, a 1973 horror/comedy where everyone who’s greedy ends up gory; Man Bites Dog about the media’s undue interest in serial murderers, and Baxter, told from the point of view of a murderous bull terrier. Shakes The Clown is also pretty dark while also being a laff-riot.
Repo Man is one of my all-time favorite movies; it’s dark, sardonic, violent, and funny as Hell, and it has the most kick-ass soundtrack to ever grace a movie.
Lastly, I don’t know about anyone else, but I think Whatever Happened To Baby Jane and Hush, Hush, Sweet Charlotte are pretty hilarious when they’re not being horrific. So’s Stuck, a more recent horror comedy crime flick based on a true story.
My recommendation as well.
I love black comedy.
After seeing some of these suggestions I’d like to add Series 7: The contenders (2001).
It’s about six contestants on a reality TV game show where they are killing the other contenders to be the winner. The movie focuses on the returning Champion who is a pregnant woman and the show takes place in her little hometown.
Looking at some of the actresses I also saw Nurse Jacky (2009-2015) which intrigued me but I don’t watch enough TV.
I was going to suggest that.
That’s weird, I thought The Hudsucker Proxy was in B&W too. Is two people enough to qualify for it being a Mandela effect?
According to this trailer, there were some ‘newsreel’ scenes in the movie in B&W, and a lot of the movie had a washed-out color palette (though other parts were pretty colorful).
The mention of Four Lions reminded me of Secondhand Lions, which goes pretty dark at times.
Has no one mentioned The Death of Stalin?
Brilliant. Hilarious. Dark. (And reasonably historically accurate)
For that matter, The Lion King gets dark. Well, as dark as one might expect for a family film.
I really enjoyed this one. Great cast. As for horror, I saw it was characterized as such and watched it, anyway. Mama don’t do horror 
and it turned out to be dark and weird but fun.
The first one I ticked off the list. The wife and I loved it - thanks!
Yea, I find it bewildering that it is so obscure. It’s just so well done, IMO.
Yeah, well, that stuff happens, I guess. Raise your hands if you’ve seen “Out of the Furnace”. Stunningly great movie - fantastic cast - seems forgotten. And the movie I started this thread with “Filth”, James McAvoy deserved the Oscar for that - hands down.
But politics, ad budgets, etc…
Seconded. Probably the darkest comedy I have ever seen (or certainly equal to Dr Strangelove).
Bad Santa
Fido is more satire than laugh out loud, but I adore it.