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.
    • It also depends on how fast the water is flowing. Fast enough and it can literally sweep someone off their feet, with rather less comical results.
  • 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.
  • A lot of people loved giving characters weird names.
  • 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.
  • Killing everyone on your party (without the Total Party Kill methods) before the first fort not because of a Self-Imposed Challenge, but because either the Random Number God 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.
  • In the second and fifth editions, it is possible for party members to die from such lethal ailments as a bad cold.

Alternative Title(s): Oregon Trail