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Shenmue I and II

While they were technological marvels at the time that created immersive and lifelike worlds unlike anything seen before in gaming, they are incredibly user-unfriendly and I honestly don't think I could ever go them now, the gameplay is so obtuse and clunky by today's standards.

Okami

The art style is gorgeous and I loved it back in the day, but nowadays there are a mountain of annoyances from the fiddly implementation of the paintbrush to the slow dialogue that add up to make it more frustrating than fun.