The Oregon Trail/Funny

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 pathetic they can actually drown in ankle deep water.
  - W-what? How is that even possible?!
    - Some people are literally just Too Dumb to Live.
      - Fact:If the pool of water can cover you face you can drown in it.
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. I once encountered one that said "I'm Dead".
In the fifth game, an attorney's office in one of the starting towns: Dewey, Cheatum & Howe.