Gabriel Knight 3: I don't know how many times I heard/saw Gabe get sliced to death with that swinging blade. Though the most painful puzzle might be the globe puzzle in The Journeyman Project Turbo. As while I know my geography the use of the trackball was awkward and at times difficult and toss in it was a timed puzzle too, I remember cursing my computer many atime. Then there's the Myst rocketship puzzle which was impossible because of my tone deafness.
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