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This game doesn't run on Windows 10 and as far as I can tell, GOG has not addressed this issue or offered a patch to make the game run. I loved the original and am disappointed that GOG would sell a game in this state with no warning or explanation. Before you ask, yes I downloaded DirectX drivers and changed the resolution. Please correct me if I am wrong GOG, but it kinda seems you dropped the ball on this one.
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So after testing out a vareity of different configs, it turns out to make Telltales Sam and Max games work on Win10, you need to ...drum roll.... unplug your Xbox 360 Controiller.

A bit random, but it works.
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PanzerFranzz: So after testing out a vareity of different configs, it turns out to make Telltales Sam and Max games work on Win10, you need to ...drum roll.... unplug your Xbox 360 Controiller.

A bit random, but it works.
That's because Microsoft changed directinput in Windows 10 and Telltale games have a strange way of using the dll.

You CAN use the XBox 360 gamepad, if you download a Windows 8 version of the dll and copy it to the game folder.
Telltale never bothered to patch that.