Ultima: Exodus for the NES.
Obtuse, impossible puzzles? Mhm.
Nonsensical leveling scheme? Definitely.
Obscure characters and classes? Right on.
I still loved this game, probably mostly because the music in various parts sucked me in and the plethora of classes was intriguing. I still don't know why you are stuck to level 5 without the Mark of Kings, why you cannot increase stats except specific shrines and why combat EXP is given to whoever dealt the final blow to th enemy, but I killed a LOT of time in this game.
Wizardry V: Heart of the Maelstrom
Multi-level puzzles with unique and often confusing logic? Yuppers.
Aging characters that can die of it? I believe so!
Level design that has traps that can literally kill off your entire party... with no recovery? Uh huh.
Again, music drew me into the game and I poured TONS of time into it. I never beat the game. I lost my best party at one point to the dreaded death-room which killed your characters and basically made them unusable ever again. Good times!
Darksun 2: Wake of the Ravager
Game-stopping bug that prevented you from winning? Got that!
Game-crashing bugs that loved to manifest randomly? YAY!
Game-mechanics that made no sense and were useless? Totally!
One of the first games I ever played with CD-Audio. I remember plunking that CD into my stereo just to listen to some tracks after school. The game itself WAS a rather interesting D&D adventure that was varied and interesting, but man the game didn't seem to want to be played at times.
Looking at a lot of the games people put in this list so far makes me feel like a really, really old man.
