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.