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Hitoshura on Digital Devil Saga. For an RPG boss, Hitoshura isn't just hard, he's cheap and also takes around two hours or more to beat, something I've never done and never plan on doing, especially after seeing what you have to do. Too long, memorization bullshit, good chance at randomly dying, etc.

Sturm on Advance Wars. The battle is ridiculous, and if you screw up once consider yourself dead. Throughout the entire battle you also have to trick the enemy into using meteor on a group of useless allies.

The chess board on DMC3 Dante Must Die mode without Super Dante and Nevan.