Games with the best multiple endings system (or choices overall)

[ObserverStatus]

For many reasons, I thought that The Stanley Parable had a great system of endings and choices, but the most important was the narrator's comment that the ending was whenever I stopped playing the game, and his constant insistence that if I wanted something to end I could simply exit. The narrator saved Mass Effect 1 & 2 for me. I learned that I could simply feed Shepard to Morinth at the end of the game, stop playing the trilogy, and it would be just as "real" of an ending as that pretentious tripe we know to be generally know to be canon.

 

[communist gamer]

planescape: torment have some cool endings, some that you can achive very qucikly (undead throne ending, the skull master ending) and the last three ending depend on your actions and how much of the story you went through). Vampire the masquerade blodlines has some cool endings, the best part is that they are not based on your choices through out the game, but based on what you learn. You can do any ending not matter what you do in the game. Deus ex of course

 

[G00N3R7883]

I really like how Mass Effect 2's suicide mission works. Based on your choices in missions throughout the game, whether or not you've upgraded Normandy's systems, and choices in that final mission, you can have pretty much any outcome from everybody surviving or everybody dying and everything in between.

 

[Xaio30]

Chrono Trigger had 13 different endings depending on when you beat the final boss.
The world changed accordingly. It was quite amazing for its time.