History Funny / TheOregonTrail

* Picturing how a party [[VendorTrash who own nothing but useless items like a huge collection of grandfather clocks]] would survive.

--> 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."

* If one of your party members comes down with an ailment, 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:

* 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]].

* 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?"

* In the second and fifth editions, it is possible for party members to die from such lethal ailments as [[https://www.youtube.com/watch?v=ukFDpVr0I8c a bad cold]].

* 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.

* In the second and fifth editions, it is possible for party members to die from such lethal ailments as [[https://www.youtube.com/watch?v=3VojQKsJ64E a bad cold]].

* 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!"]]

* A lot of people loved [[HelloInsertName giving characters weird names]].

* 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.

* In the second and fifth editions, it is possible for your character to die from such lethal ailments as [[https://www.youtube.com/watch?v=3VojQKsJ64E a bad cold]].

* Killing everyone on your party (without the TotalPartyKill methods) before the first fort not because of a SelfImposedChallenge, but because either the RandomNumberGod 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.

* 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.]]

* 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]]''.

* 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.

** TruthInTelevision there. Some people (children especially) are so pathetic they can actually drown in ankle deep water.

** 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?]]

* 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]]''. I once encountered one that said [[CaptainObvious "I'm Dead".]]

** A ShoutOut to ''Film/TheThreeStooges'' is always good for a chuckle.

*** W-what? How is that even possible?!
**** Some people are literally just TooDumbToLive.
***** Fact:If the pool of water can cover you face you can drown in it.
***** Fact: If a river is deep enough to reach above your thighs, it has potential to move with enough power to drag and drown someone. It's also possible for someone to slip and fall, and then even a calmer river can drown them.
***** Fact: If you think this is a very likely event to happen to you, don't go on the trail. You're just asking for it.
** I'd originally thought it was FridgeLogic but hey, I think there were babies being taken along this trip. Mystery solved.

** A ShoutOut to ''TheThreeStooges'' is always good for a chuckle.

* 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]]''. I once encountered one that said [[CaptainObvious "I'm Dead".]]

* In the fifth game, an attorney's office in one of the starting towns: [[AmoralAttorney Dewey, Cheatum & Howe]].