Philisophical Gaming: A.K.A. How Heavy Can You Get?

So, here's a question for the blog, rather than my usual spiel about internal thoughts.
How heavy can you get?
Let me explain: People like thinking. Well, let me amend that: MOST people like thinking. And game that make you think, are the best. Games that give you deep, heartrending questions and choices with no clear answer. People like that because... hey, that's how life really is!
So, what's your favorite game that made you think? Alternatively, how dark adn heavy should games get? Is there a line that shouldn't be crossed? I'd like to hear your thoughts.
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