IVAN. It's a rougelike where one of the main design goals was to make the game unbeatable. I've probably played it a hundred times, and never got past the second dungeon (out of three). Plus, it's free.
The Elder Scrolls 2: Daggerfall, if you choose all your skills as language skills, and take as many advantages as possible. All of your useful skills will start out super low, and you will level so slowly that it will take ages before your character improves a noticeable amount, making the game super difficult.
The Elder Scrolls 2: Daggerfall, if you choose all your skills as language skills, and take as many advantages as possible. All of your useful skills will start out super low, and you will level so slowly that it will take ages before your character improves a noticeable amount, making the game super difficult.