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."