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Conkers Bad Fur day is probably the game that made me laugh the most.

Games from LucasArts in its prime are also up there. Curse of Monkey Island comes to mind.

Mario RPG games like the Paper Mario series and the Mario Luigi Games all have great humor.

But even so, I think my personal top tier have to go to the lego games. The way that they create known worlds like Star wars and Harry Potter in lego is hilarious and the cut scenes are always fun. Even if the gameplay can be wonky at times the way that they handle the IP, brutally dissecting them brick by brick for funs sake makes them my top choice for fun games.