2. I Wanna Be The Guy: Gaiden
http://youtu.be/Ixgagswag8M Got an hour and 40 minutes spare? Then why not check out the above clip, which shows an expert gamer being reduced to a husk of a man in front of a live audience by this game, I Wanna Be The Guy: Gaiden, the most infuriatingly impossible game I think might ever have been created. The game itself is a homage to those impossible titles of yesteryear and features more retro gaming references than you can shake a NES controller at, although you're lucky if you can actually progress far enough to see any of them (jump to 1:35:30 in the clip above to check out my personal favourite). If you were to speed run this game without dying, you'd probably be done in ten minutes. However, you will die, over and over again, more times that you've ever died on a game before no doubt; as it'll take you much longer than the actual length of the game. Most people will never beat this game and those who do, at what cost? At what cost...