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.
• 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!"
  • Some of what your children say when you're travelling can also be pretty funny. Two of such quotes: "I am a banana!" and "I am the queen of France!"
• 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.
  • 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?
• 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.
  • A Shout-Out to The Three Stooges is always good for a chuckle.
• 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. In the 1800s, of course, this was very much Truth in Television.
• One of the people you can talk to in the second and fifth versions is a boy who will simply ask "Which way is west?"
• Asking for advice on what to do during a severe thunderstorm in the second and fifth versions. Three of the four people recommend waiting it out. The fourth one...
  Man: Are you scared of a little storm? What's the matter with you?
• If one of your party members comes down with an ailment in the second and fifth versions, its symptoms will appear in that member's status. If someone is unlucky enough to have more than one at the same time, the symptoms of each will be listed in alphabetical order. For instance, this is what will show if someone has a bad cold, a rattlesnake bite and a sprained ankle all at once:
  Symptoms: Blurred vision, coughing, disorientation, dryness of the mouth, fever, Nausea and vomiting, pain, runny nose, slurred speech, sneezing, sore throat, swelling and internal bleeding, swollen painful joint.

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