It's hard to say which has been the oldest. My first gaming experience was in the mid 90s when I was visiting my uncle abroad, he had a PC and the original SimCity - I somehow knew then that it wasn't my kinda game but of course I played it for hours anyway.

Deus Ex (2000) - a game that pushes the boundaries of what the video game medium is capable of to a degree unmatched to this very day.
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