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The most I ever spent on a used game was $45. During the 32/64-bit days, I picked up SNES Final Fantasy III (VI) and it came in it's box with the instruction manual.

The most I paid for a new game was an embarrasing $70 for Star Wars: Shadows of the Empire when it was new. That game was hard as hell to find at that time, I could only find it at Shopko, and they were charging premium price for the thing.