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Would we be stuck in a little room with a TV playing the game, or in the actual game world (though the world appeared to be reality, and could be expanded to all logical realms of the game world)

If it is the latter, I would want to be trapped in SM64 or Harvest Moon64, prefferable harvest moon. If it was reality, there would be a city where your father worked, and that stretch of land in between, everyone would conceivably be immortal since no one seems to age, and there are mountains/valley ect instead of blackness. Mario 64 I would imagine you could fly off the island back to mushroom kingdom via special kap with peach after lollygagging around her castle for 50-2000 years.

Play a game? It would need to be something that is no pressure, because if you die you are gone. Probably... harvest moon 64

So my final answer is harvest moon 64, one of my favorite games ever. Super Mario Sunshine would also be a pretty good pick.