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Probably 1000/1000 Cal of Duty 3 which was just a dreadful experience all the way through.

After that I would say my single hardest one so far was It's all in the Trial from Dante's Inferno ... it was a DLC coop achievement that me and this other guy I found on xboxachieves.org spent about 2 weeks on. That achievement will test your patience and I almost gave up so many times.

A lot of people seem impressed that I 1000/1000 Two Worlds 1 as well ... not that it is hard it is more an endurance thing for being such a long and bland game.