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JohnVG said:

Probably Portal 2.

But Sonic 1 (MD), SM64, Chrono Trigger, MGS1, Halo, Breath of the Wild... could also be good candidates, and they are from all my life.
I probably forgot some... like Metroid Prime, for example.

And I don't know if I would play Ocarina of Time for the first time again. I feel... the game has aged not that well. And I love Ocarina of Time, I played it a lot, I knew every secret. But... that was NOT the question. Even when it was still a "new game"... I read some "reader's letter" (in some videogame magazine) with a heavy criticism against Ocarina being too mystified from day 1 in the media... and whoever wrote that letter, was harsh... but... he for sure played the game, because (I remember) I thought he had some valid points there (not all of them necessarily getting my support, but valid nonetheless).
Anyways, Ocarina was great in its day, no doubt... I suffered from the Ocarina-mania fever as many millions had, during some years, and I remember "the magic" in my first games. But its gameplay would need some serious improvements today, because many things that in 1998 were just little raw edges not that well polished... now would be NOT tolerable anymore (one example: the need to CONTINUOSLY pause to change the boots... that alone... would be a reason for dismiss the game not only as the greatest game, but from the top 100. In 1998 though, you simply paused and unpaused 23 times per minute in the Water Temple, with no complaints.

Yeah part of the OoT magic was getting stuck and discussing with friends how to continue. OoT was a product of its time and indeed there are better Zelda experiences now for my kids.

OoT stays in my top 30, but has been moving up in my top 100 as well.

Why not the original Portal though? To experience that fresh again would still be great. But you would have to forget about Portal 2 as well (and Prey). Portal 2 was an upgrade in every way but the mechanics were not new anymore.