Funny: The Oregon Trail
aka: Oregon Trail
- Encountering a body of water barely deep enough to reach your knees (or lower) and not only still managing to drown yourself, but your entire wagon party.
- Truth in Television 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 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 "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 hilarious.
- Anyone who's ever played the oldschool Apple II version commonly found online has encountered the legendary "Peperony and chease" epitaph. 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: Dewey, Cheatum & Howe.
- If you die via the second game's Kaizo Trap, 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.