Funny / The 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!"
  • 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 hilarious.
  • 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.

Alternative Title(s): Oregon Trail