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I actually thought Legend of Kyrandia was decent. Also when you mention Legend of Kain are you talking about Blood Omen: Legacy of Kain because that was pretty good, Legacy of Kain: Soul Reaver was decent as well.

One of the first bad games I played that really stood out was Advanced Dungeons and Dragons: Heroes of the Lance. I was a big Dragonlance fan so I couldn't wait for the game to come out (I waited eagerly in anticipation for months). When I finally got the game home and started playing I got upset at how bad it was and actually said "What is this shit?!?". It was a pretty big letdown.

Another would have to be Ghostbusters 2. I really enjoyed the first Ghostbusters game (on Commodore 64, apparently the console versions sucked) and was extremely disappointed by the second game that was just complete crap, I was also disappointed by the second Ghostbusters movie as well.