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The Sims and all Pokemon Games come to mind immediately

Ultima Underworld 1 & 2 (slightly favouring 2)

This is hard to answer - it's been a while, i think it was Summer Games for C64

No - i've never broken one in anger, but over the years many broke of old age.

I prefer digital copies wherever possible, but physical copies are OK too - just take more space.

Getting a C64 for educational purposes and then discovering that it was far better for gaming :-)