I don’t know about you but I pride myself on being a good guy in most games. I choose all the light side options in KOTOR and I always donate to virtual homeless people.
That said, there are some morally ambiguous quests you just can’t talk or donate your way out of, and the Elder Scrolls series has a bunch of them, especially since some of the best quests in the game come from the Dark Brotherhood, an organisation of assassins for hire.
While sometimes the nasty things you encounter in the series’ most disturbing quests are your fault, sometimes they’re just things you happen across. Whatever the case, Elder Scrolls games are a masterclass in narrative-building and genuinely engrossing side quests which makes them all the more impactful when things take an unsettling turn.
Honestly I could easily have made this list twice as long with all of TES’ gruesome quests so be sure to tell me your favourites that I missed down in the comments.