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I made a thread a long time ago called "games so nice you bought them twice" and I was pretty disgusted by how many times I've double, trippled, and even quadruple dipped. I think there are a few games I've bought five or more times on different hardware (if you include updated versions of games like Tomb Raider 2013 and Metal Gear Solid 3).

Right now, I don't even want to think about it--but I know there's a ton of games added to the list.