Any of the Gold Box series. You oldschoolers know what I'm talking about. ESPECIALLY Eye of the Beholder and Eye of the Beholder II (forget III, that was a piece of crap), as well as Dungeon Hack and Stronghold (1990).
Daggerfall. If it wasn't for this game's legions of fans (including myself) on uesp.net and TES: The Essential Site, Morrowind would never have even existed.
Fallout 1 & 2. What else is there to say? If you haven't played the Fallout series, you cannot consider yourself a real role-player.
Baldur's Gate I & II (plus expansions). As above, if you haven't played the Baldur's Gate series, you cannot consider yourself a real role-player.
Castle of the Winds. A Rogue-like game for Windows 3.1 (but works perfectly fine in XP) that was once shareware, but released years later as freeware.
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