The oldest adventure game I gave up on was Infocom's ultra-challenging Spellbreaker. I believe it was the last Infocom game I even played, back in 1985.
More recently, I tried my hand at The Black Cauldron, and got pretty far before I got fed up with being repeatedly killed and abandoned it. Maybe one day I'll revisit it and finish it, because I actually liked most of the game quite a bit.
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