* 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 pathetic 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!"]]
* 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 DOS 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.