DR. STRANGELOVE OR: HOW I LEARNED TO STOP WORRYING AND LOVE THE BOMB
This is the best example I can think of in the category "smart comedy": films with actual plot, characters and substance that are still funny as hell. This particular flick is a pitch-black Cold War commentary that shows the complete insanity of Mutually Assured Destruction and everything surrounding it. But despite that, it still manages to be really really funny, with multiple masterfully played roles by Peter Sellers.
If you liked this, may I suggest: The Big Lebowski, or pretty much any comedy by the Coens. Woody Allen has some decent ones too: I especially recommend Vicky Cristina Barcelona, which is absolutely delightful.
FIGHT CLUB
Don't be deceived by the title. It might look like a shallow action movie at first, but if you look closely this is an incredible commentary on what anarchy, violence and having a penis means in the modern day. Combined with brilliant acting, Tyler Durden, a mind-blowing story and possibly the best ending ever, this is a must-see.
If you liked this, may I suggest: A Clockwork Orange or Taxi Driver, if only for the style.
FINDING NEMO
Or any Pixar film, really. Besides its ground-breaking work with animation, Pixar has done something that hasn't been pulled off since Walt Disney himself was alive and kicking: it has made the term family-friendly mean something again. The films are genuinely fun for everyone to watch: funny without being childish, engaging without becoming too complicated. Combine this with colorful animations, memorable characters and jokes that are actually funny, and you've got yourself a winning combination.
If you liked this, may I suggest: Wallace and Gromit have to be mentioned, just like The Nightmare Before Christmas. If you are looking for a little more adult animation, check out the works of Hayao Miyazaki (Spirited Away) or Persepolis.
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