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What is the most intentionally funny movie you've seen? (Tries to be comedic, succeeds.)
What is the most unintentionally funny movie you've seen? (Tries to be serious, fails.)
What is the most intentionally unfunny movie you've seen? (Tries to be serious, succeeds.)
What is the most unintentionally unfunny movie you've seen? (Tries to be comedic, fails.)
 
life suicide GIF by David
 
Intentionally funny: Either The Big Lebowski or Black Dynamite. The Big Lebowski is Coen Brothers gold, with so many jokes per second you need to rewatch it to pick up everything going on. (Protip: Don't waste time trying to figure out the "mystery", as it leads nowhere. Enjoy the film for its ridiculousness and you'll appreciate it more on the first viewing.) Black Dynamite is a great send-up of old 70s independent films. It is brilliantly written stupidity at its finest.

Unintentionally funny: Cats. The original stage version (or the straight to video adaptation of it) is a hilarious acid trip of nonsense writing that'll make you wonder why cocaine itself never won a Tony award in the 80s (or the full EGOT, for that matter). The film version is evidence that director Tom Hopper is a talentless hack who can screw up even when given a story that nobody expects to make sense.

Intentionally unfunny: There's a lot of films with zero comedy to them. Grave of Fireflies might be the best choice for this I can think of off the top of my head.

Unintentionally unfunny: Team America: World Police. Worst comedy someone else insisted I "needed" to watch. (Hold your pitchforks, Parker/Stone zealots. I did exactly what you wanted and censored out any details that would make your comedy gods look bad.)
 
What is the most intentionally funny movie you've seen? (Tries to be comedic, succeeds.)
What is the most unintentionally funny movie you've seen? (Tries to be serious, fails.)
What is the most intentionally unfunny movie you've seen? (Tries to be serious, succeeds.)
What is the most unintentionally unfunny movie you've seen? (Tries to be comedic, fails.)

I definitely struggle with absolutes, but let me come up with something here.

Intentionally Funny would be...oh, any great comedy. Let's say Caddyshack (1980) for the moment.

Unintentionally Funny could apply to anything that's been on MST3K...Cry Wilderness (1987)!

Intentionally Unfunny, pick a company training video, I've yet to see one with a sense of humor.

Unintentionally Unfunny...Men at Work (1990). Nary a laugh to be found.
 
the ones that really amused me:

Police Academy
White Chicks
Big Mamma's House
 
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