#50: Monkey Island 2: LeChuck’s Revenge (LucasArts, DOS, 1991)
In the original, the occasional tendency to act a little dishonestly when it came to matters like safes and credit notes was about Guybrush’s worst moral flaw, and he at least had an important quest to justify the means. In Monkey Island 2, a newly cynical Guybrush lies and cheats constantly, steals a visually-impaired man’s monocle, saws off someone’s wooden leg, gets a woman falsely imprisoned, and nails a coffin salesman inside one of his products. The game helpfully keeps track of these on a regularly updated wanted poster, if you’re interested. It’s all done as comedy, but it still feels like an earlier, much more subtle take on that modern video game thing of rubbing the player’s nose in what they’re willing to do because a game guides them to.