I can go back and play Zelda Ocarina of time as well as Majoras Mask on my N64 and very rarely do they ever feel dated. Maybe this is nostalgia talking, but I think that a lot of my N64 games have been lasting and replay value than most of my Xbox 360 games.
Two game (serie)s come to mind immediately.
The first is Monkey Island (1990), which had a recent re-release of course.
It did well enough for the sequel, another game that held up well, to get the same treatment.
The other is Commander Keen (1990), or really most of the Apogee/id Software platform games.
Oddly enough, I would posit that Halo: Combat Evolved has aged extremely well. Its campaign is still thrilling, the soundtrack and sound design are still top notch (there's nothing like hearing the crack of a sniper rifle or Halo's signature "ba-da-da-DUM" as you slaughter a pack of Grunts), and (surprisingly) the graphics still look weirdly pretty. And few multiplayer experiences can top the adrenaline surge you get while playing 16 player CTF in Blood Gulch.
I think as a whole, the Super Nintendo classics have aged the best. Mario, Zelda, Metroid, Castlevania, MegaMan, FInal Fantasy, Chrono Trigger, Mario Kart, etc.
All of the SNES versions of these games are still finely tuned and pleasing to watch games.
Silent Hill 2 has a great graphical style that, while not eye-poppingly impressive, is enough to keep it scary and immersive when other horror games from around the same time look cartoony by comparison, such as Code Veronica. (Although I do love CV, it's probably the most underrated Resident Evil, it's absolutely dicks on 4!)
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