Takeshi no Sengoku Fuuunji (Japan)
This game, often known as Takeshi's Challenge, is often regarded as one of the hardest games ever made. This is not due to actual difficulty, (with the exception of a certain section) but instead just how painstakingly exact everything is. It starts out with you having to straight up leave your job, and continue on to divorce your wife (as a side note, you can also choose PUNCH instead of PAY ALIMONY). Wow. I am absolutely speechless. Takeshi...I...I don't even know what to say about that. This game cannot be correctly described, as it isn't correct. Takeshi, you broke life.