Playstation 1 games look horrible in general:

The first Tekken, for example... UGH!
I believe that the earliest game that I can return to without being turned of by the horrible textures is Half-Life.
Playstation 2 games can mostly hold up their own if they are artistically well done.
This generation of games might look somewhat old in 20 years, but they won't be frowned upon I think. Naturally, handhelds might be doing way more than that by then.
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