No games that intentionally try to be funny have ever made me laugh. It's hard to make me laugh, especially if I'm playing alone (for whatever reason I'm prone to laughing more when someone else is around).
However, there is one game that absolutely had me clutching my sides in pain due to laughter, and that's Stick Fight: The Game. I was playing it with my cousin a little while ago, and just the fast paced ridiculousness of the game makes it incredibly hilarious. Some of the deaths/kills are just so random that you can't help but laugh. It's like concentrated comedic timing.