Technically, mine would be Icewind Dale - I bought the D&D pack and this is the "last" title listed in that. IWD was sort of icing on the cake - I bought the pack to immediately play a few of the games and knew some of the others would be on the backburner for the foreseeable future.
If I count playing the games I wanted to play in the D&D bundle as "D&D bundle played," next up would be Magrunner, but that was a freebie.
The oldest still unplayed game I bought would then be... Anachronox. I always wanted it and never picked it up on release. Not sure why I haven't fired it up yet to be honest.
I really like this thread by the way!
budejovice: My first purchase was during a large sale in September 2013. In addition to the freebies, I bought, and have not yet
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Amnesia - The Dark Descent You should play this, pronto! It's not even one of my usual genres of choice (horror puzzler / adventure I suppose?), but I had a blast playing this one. It's a very good game, and doesn't really require a huge investment of time so it's not a bad one to pick up and play next time you're looking for a game but unsure what to go with.