I'd definitely recommend Monkey Island 2 to anyone who hasn't played it, because it's one of the best games ever made. It's LucasArts at the top of their game, and there's a sense of creativity and discovery throughout that hasn't been replicated in any other adventure game.

I just believe that because it holds together so well, a lot of people have read more depth into it than was there, or was needed for that matter. A long, fun comic pirate adventure story has enough merit on its own without needing to be over-analyzed.