For me it's Caves of Qud. I love roguelikes and games with impenetrable control schemes and UIs. Took me a long long time to get the hang of Dwarf Fortress, but once I did I fell in love. But of course, I was younger then, and had much more time available.
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Look up min-max guides for Oblivion before you dive in. The leveling system is bad. You want your major attributes to be stats you don't use regularly. You can accidentally level too quickly and not have enough points to keep up with the world scaling.