9. A Happy Couple - Floyd
Floyd is a delightful point-and-click game that really deserved to have been picked up by fans to the same degree many Monkey Island-esque games did, as it does deserve that kind of cult following, if only for how weird it is.
It also involves you being kind of awful on occasion. For example, when you want to get into a phone booth that is currently occupied to get changed, you decide the only logical option is to ruin the life of the guy currently using the phone.
Despite the fact you could, in theory, get changed somewhere else, your plan - in true point-and-click form - becomes getting the guy on the phone so drunk that he ruins the conversation with his girlfriend, breaking them up.
If breaking a couple up to get in a phone booth wasn't bad enough, you also then become indirectly responsible for for said girlfriend's death, as her grief in public is a civic crime, the punishment of which is execution.
Hope getting changed was worth the murdering a totally innocent individual by playing with their emotions, you monster.