Many of my games I've bought two of, my sister and I share identical taste in games, so often when I buy a game for her I buy it for myself as well a few months later.

I'm trying to think of a game I've bought three times, but nothing comes to mind. Oh wait, Resident Evil. First I bought an american version, which obviously didn't work, then I bought a PAL version. It got scratched, so I bought a new one, which was platinum by then. Then I bought the remake for gamecube whenever that one was released. I think maybe I bought Clock Tower 3 three times as well. Once for my sister and twice for myself.