Planescape: Torment is extremely replayable. I've been playing it every few years since I got a copy in I think like the early 2000s. It may be that this has something to do with having gotten to play it a little bit in the 90s but not having gotten to play the whole thing. There was a lot of anticipation there.
But I don't think it's just that. It's incredibly responsive to choice, and it's one of the first games I can recall with things like faction reputations and alignments. There's a lot there to dig through, and even once you have, it's always cool to wander around Sigil. It feels very alive.
The other one I end up replaying over and over is Shadowrun for SNES. That's not so much infinitely repayable though as just a really great game that I'm happy to run through.