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A few from my top 50.

DW3- Hard mode on certain levels... Crossbows and one hit combos from certain officers. Play a 70 min battle, half health from successfully maneuvering about. Get hit by a few bolts from nowhere and die. Ragequit.

ROTKVIII and Digimon World- MENU MADNESS

Uncharted 2- The ridiculous ai that hit you with every single bullet, yea.

World of Warcraft- the fact that it is an MMO, and thus requires my friends to get online at the same time as me. Rarely happens.