I can think of some obvious examples to start with, but my subtle but insidious nominee is Fable III. Fittingly for a pretentious grifter like Molyneux, the game requires you to raise a specific amount of gold or your kingdom is destroyed and you get a bad ending. The goalposts are moved by the game if you raise money in ways it doesn't approve of, and it is simply impossible to reach the fundraising goal in any way that isn't at least Enlightened Centrist levels of evil, the kind that lanyard-wearing neoliberals giggle about. That's right, you need to be at least this evil or your kingdom is destroyed. So deep and really makes you think about the hard decisions that are made by the ruling class, doesn't it? :zizek:
My favourite ending for Dishonored 2 is high chaos Corvo.
spoiler
If you refuse to undo the curse that turned Emily into a statue, there's no-one left in line to the throne and most of aristocracy is dead so Corvo just declares himself king instead. If the Duke and his body double is also dead, Corvo just declares himself Duke of Karnaca as well. You just end up with Corvo alone and paranoid having ligma grindseted his way into royalty.