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Many WoW bosses, including some first bosses of the raid...... GD you Attumen.

If that don't count, then I say being underleveled for any jrpg boss. Heck my friend dislikes random battles and runs away every time, then he gets to Dhoulmagus and cannot beat him without grinding for hours (the hours he skipped),

Okay seriously now, for some reason I had the most difficulty with a hard corps uprising boss.