Here's one no one on here will have played, though probably not what you're looking for. Mastermind: World Conquerer. A free flash game where you plot to destroy the world, managing minions to run evil operations like robberies and assassinations, while reseaching evil science to destroy the world, and guarding your evil lair from attack until you're ready to execute the ultimate plan. Moon base is totally OP. Probably one of the best completely free games I've ever played. It's basically a parody of the evil mastermind trope, except you win. Lots of humor and charm. Available on Kongregate and Newgrounds. I'd love to see a AAA game based off this concept. Same charm and humor of seeing things from the evil-for-evil's-sake mastermind villain's point of view, but on a much, much larger scale that only a console game can offer.

Of course, I'd also love to play a game with a Watchmen style "villain with good intentions actually wins" story, in which you actually play the villain and win, but doing so is beneficial to humanity, forcing the audience to question their view of morality, but that will likely never happen...

Heavy Rain, if you ignore QTEs

If you ignore QTEs, Ethan is stuck sleeping on his bed at Jason's birthday. I wouldn't qualify that as evil triumph, unless you hate Jason!

Thats somewhat true, but I am talking about any game where your decisions have a positive or negative effect on the world you're in. The decisions cultimate in either the positive progress or the destruction of some sort of order or even no changes at all. 

Any WWE game ever! Pick a heel and go nuts!

I was going to say KOTOR but evil still doesn't quite win, really....

You know what I mean - if you ignore the critical QTEs. I actually did that to see what happens.

Every time non-finished games releases and sells millions despite being totally panned, evil companies win.

Uncharted...Nathan is a murder...


/jk

Infamous second son? Demon's souls?

Love the conversation around TLoU... Though reading spoiler text on a tablet requires a lot of effort.

One of the best XBLA games I've ever played reveals at the end that you were actually evil and possibly insane. I'd love to name the game but simply naming it would be enough to rob anybody of an amazing experience should they choose to play it.

Lemme guess, the main character wears a suit? And loves watching "sunsets"?