* Encountering a body of water barely deep enough to reach your knees (or ''lower'') [[EpicFail and not only still managing to drown yourself, but your entire wagon party.]]
** TruthInTelevision there. Some people (children especially) are so pathetically weak that they can actually ''drown'' in ankle-deep water.
* Having a member of your wagon party break a limb or become inflicted with a nasty illness, only to tell them to either do extreme exercises or binge drink on laudanum to (somehow) cure themselves.
** Better yet, sometimes ''it actually works!!''
* Picturing how a party [[VendorTrash who own nothing but useless items like a huge collection of grandfather clocks]] would survive.
* In the iPod version: Being attacked by a bear. One of your children will ask what they should do, and another will quip [[VideoGame/StarFox "Do a barrel roll!"]]
* For some reason, the picture you get when an ox is sick.
* The Mega64 spoof. Poque dying repeatedly of things you can't even die from in the game (like cancer), one of the other guys trying to buy a movie called ''Pelts'' in lieu of real animal fur ("I've been looking for this!") and some food with an actual strip of bacon. Also a rare case of someone possibly realizing they're parodying a video game.
* As anyone who has played the game on a school computer can attest, some of the epitaphs left on the trailside grave markers are ''[[BlackHumour hilarious]]''.
** Anyone who's ever played the oldschool Apple II version commonly found online has encountered the legendary "Peperony and chease" epitaph. [[http://www.youtube.com/watch?v=vKspf06XuaQ Hey, they asked what he wanted on his tombstone, didn't they?]]
* In the fifth game, an attorney's office in one of the starting towns: [[AmoralAttorney Dewey, Cheatum & Howe]].
** A ShoutOut to ''Film/TheThreeStooges'' is always good for a chuckle.
* If you die via the second game's KaizoTrap, it leads to all sorts of hilarious situations, such as operating a mine, opening a business, getting elected to a city council, and raising money for Civil War widows and orphans despite being dead the entire time, which gives the impression that you came back as a zombie, or that everyone around you is clinically insane and believes that a dead person is still alive.
* Killing everyone on your party (without the TotalPartyKill methods) before the first fort not because of a SelfImposedChallenge, but because either the RandomNumberGod has never liked you ever since you played the game for the first time when you were seven, or because you just suck ''that much'' at the game.