Very Dark Comedies

I'll recommend one of my favourite films of all time. However, it's black hole black. I can think of plenty of people who wouldn't agree with the description of comedy no matter how black. Also, it's B&W and Belgian, so if that's a problem for them obviously don't bother with this.


Man Bites Dog

^^I've never seen a poster which puts it forward as a comedy as much as this one does^^

WOW! How could I have forgotten about Death to Smoochy?! Great, fun watch, IMO. Same with The War of the Roses. I haven't seen that in a few decades though. I need to revisit it.

I'm sure this next suggestion is out of bounds (on a few levels), given that it's a series and it confidently pushes itself right into morbid, but the Netflix series, Happy! is about the best dark (disgustingly violent and dark), warped humor run I can think of. If the "fat scene" of Fight Club was a bit much for your friend, then likely this will not go well at all. Still, it's a wild experience and deserves to be bookmarked.

Whenever I think of dark comedies this is the one that jumps to the front of the line. I love it as well and black hole black is a very solid description.

Happiness is another really good choice.

-La Strada
-One Flew Over the Cuckoo's Nest
-Mikey and Nicky
-Buffalo '66
-To Die For

Thank you! Recently rewatched Buffalo ‘66, but that might actually work. Also like the look of Mikey and Nicky, which I don’t know.

"Mikey and Nicky" for me is a 10/10... John Cassavetes and Peter Falk are great in this. Hope you check it out!

Drop Dead Gorgeous (1999)
Go (1999)
The Death of Stalin (2017) (so dark I didn't find it funny but fits the bill)
The Favourite (2018) and The Lobster (2015) sort of qualify
Fargo (1996) I guess
Kind Hearts and Coronets (1949)

And then there's horror-comedies but that's kind of a different thing