Hmmmm yeah this is a tough one. If I went Jack's route and wanted to experience something from my childhood in gaming it'd be
Final Fantasy 8, but I doubt it'd hold up in today's standards.
For modern games, it'd have to say
The Last of Us and/or Danganronpa. Since Danganronpa is a mystery game, there isn't much value in playing it again. But the first time you play it....amazing.
The Last of Us is all about the story. You can replay it multiple times and try to play different styles, but the first time you experience the story from start to finish is always the best. I wish I could reset my memory of those two games and play them again!