Zelda II. There were countless flying enemies that would knock you into pits. Knights that could block your high attacks while attacking low (which means you cannot block) or visa versa. I remember it taking a few minutes to take 1 down and these were common enemies (God help you if you took on 2 at once). The spells required to fight the 2nd to last boss required so much magic that you couldn't cast Life.
Zelda was hard but mainly it required a lot of trial and error (how I hated running off screen so my blue candle would recharge so I could burn another bush). However, the 2nd play through (or first if you used Zelda as your name) was almost as bad as Zelda II. Dungeons were moved. I think you had to partially go through some to pick up an item needed for another dungeon. Wizards and knights were in most dungeons and were a far bigger threat then the dungeon bosses. Mini bosses were also everywhere. One-way doors (which could be invisible) could make you retrace an entire level. This was some of the most frustrating and fun gaming I've ever had.
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