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Retro is before 3-D. I can't consider Mario 64 retro, because games like it are still being made.

Oldschool is either old games or new games in the oldschool style, like the new Punch-Out!! or Viewtiful Joe.

Trying to define this stuff is always a little weird, especially with the word classic. I remember hearing Pearl Jam on a "classic rock" station and being really confused. In art history classicism and neoclassicism are tied to specific time periods, so I always expect the word to work like that with music and games too. But that might just be me, I don't know.