Hitman 2: Silent Assassin
I still really like the concept of Hitman. Stealth assassination - sneaking around and cleverly dispatching your foes, using AI and the environment to your advantage - is one of the holy grails of gaming, and Silent Assassin makes an admirable effort. But it just doesn't come together right.
Though there is always more than one route to taking out your target, each route tends to be extremely exacting in its requirements: doing just the right thing, in just the right place, at just the right time. It's not luck, because doing it correctly is 100% repeatable if you know how, but you're liable to die a handful of times in the course of learning the specific movements you have to carry out. This doesn't just make the game tedious and frustrating, but also ruins the immersion factor, which is a shame given the loftiness of Hitman's ambience. Granted, you can turn the game's difficulty down enough to fudge your way through almost any mistake with pure firepower, but this has the same duet of problems - the gameplay becomes tired and boring, and being practically invincible destroys any chance of becoming engaged in the game world.
From what I've seen of the follow-ups, Contracts and Blood Money, not much changes as the series marches forward, which is kind of disappointing; I guess there are series fans who prefer the reiteration, but I think it's a shame the gameplay never evolved into something more.
Progress: Gave Up -- Somewhere in St. Petersburg