In the old-school days of The Oregon Trail, it became common practice to play "Suicide Trail" (aka "Oregon Fail"), trying to achieve a Total Party Kill as soon as possible. There is also a lot more cruelty potential in the sequel, such as administering Worst Aid or taking the more dangerous routes. Beware though, you may be punished for it.
Spinoff The Amazon Trail literally requires you to trick a Spanish Conquistador into drinking a bottle of ipecac syrup straight in order to continue (or even escape encountering him). The Jaguar Spirit's comment on the event is along the lines of, "Well, that was mean... but some people just can't be helped."
Right in the box with the Apple ][ computers of the 1980s, there were disks that were intended to teach the user how computers work, with an intended audience from a generation that automatically thought "typewriter" when they saw a QWERTY keyboard. The introduction disk taught users about cursors in general, how to correct spelling, that 1 and l aren't the same for computers the way they are for typewriters...but when it came time to teach the user about the arrow keys, there was a simple maze game built into the introduction software. The developers of this maze game made it possible for the user to cause the playable characters (either a gnome or a rabbit) to crash into the walls, floors, and ceilings with slapstick animations, and even made it possible to send the character falling down several squares after such a collision. The character would even tap their foot in frustration while staring at the user if this happened!