L'ouvre du Todd Solondz.
Depressing to think about how hard he thought about ways to make you depressed, but you just ended up thinking, "eh."
What shames me is how I laughed when I first watched Happiness and the ending of Storytelling. I remember telling the video clerk of my Solondz chucklefest and being answered with an awkward silence and look of concern. I had to take a long look in the mirror after that.
Some hilarious family-friendly French-Canadian offerings...
Léolo - I won't summarize but here are the IMDB plot keywords should tell you something (Urination Scene, Tomato, Young Boy, Surrealism, Masturbation, Defecation, Animal Abuse, and so on...)
The Peanut Butter Solution - A bizarre "kids movie" that gave horrible nightmares to every kid in my class. No joke, I've got real emotional scars from repeat rainy-day classroom viewings.
Takeshi Miike is another director with comedic chops. Watch Audition for its hilarious surprise twist.