The first game the comes to my mind is Suda 51's Flower, Sun and Rain. The game is designed on purpose to be boring and unpleasant to play. In games characters talk about how lame you are , how ugly the game looks , and how the music is just covers of famous jazz songs. The whole experience is just to see how far you the game can push you.
Also the Takeshi game for famicom for basically the same reasons.
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