- From the opening cutscene, the narrator's line after he describes how the first Sim civilization (i.e. before the Watcher started actively intervening in Sims' lives) fell apart due to "violence, disease, famine, and Dire Chinchillas":
- Punctuated by the statue of the Watcher falling over and flattening some burning houses with a loud "THWUMP".
- This becomes funnier on a meta level if you've had issues with Sim AI in the past.
- When playing as the monarch in one of the quests, you have to ask 3 of your servants to give you an honest opinion of how you're running the country. While they're all funny on their own, talking to the jester is hilarious. Simply put, the jester recites a poem that is obviously more of an insult than anything. The monarch's response?Monarch: ...You're fired.
- When holding court as a monarch, some of the petitions the citizens approach you with can get really amusing. Of note is a guy who asks the Monarch for permission to have a child. The positive option is to tell him he doesn't need your permission for something like that, and the negative one...Monarch: Are you kidding? You want my permission to breed. You know what? No. Just because you asked me: no. You are banned from having children.
- Even funnier if you're familiar with the folk etymology about the word "fuck" standing for Fornication Under Consent of the King.
- Also when holding court as a Monarch, a villager will come to request permission to burn the vulgar shrubbery his neighbor is sculpting, and regardless of how the Monarch replies, it's a rather easy request to forget. However, another villager might come later asking for funds to make a statue of the Monarch. If you say no, s/he will reply that they shall "go back to their other pastime of sculpting vulgar shrubbery".
- If you use the Monarch to make an ally of the Crab Bandit, your reward is a fake mustache matching the bandit's.
- The Wedding quest has a hilarious speech given by the best man/maid of honor at the end. It sometimes includes "Remember that time we got caught up in that meat trade in Aarbyville?" It's even funnier if you just chose random Sims who didn't have an established friendship before the quest.
- Gossip can be hilarious, because it just plugs random Sims' names in, even if they're hero Sims whose traits or past quests would indicate the exact opposite of the gossip. You'll get something stupid being done by someone Scholarly, or someone who's Chivalrous supposedly courting three people (or someone that you consider, or designed to be, rather ugly being "attractive enough to get discounts at all the market stalls by smiling"). Then there's "I heard (Sim Name) wasn't really born in (Kingdom Name) at all. Show us the birth certificate, I say" which is funny no matter what but funniest when they put the Monarch's name in there.
- Though there is a quest where the knight can find out that they indeed are not nobles, making that gossip accidentally true. Might just make it funnier though, considering that some peasants might know this long before the person themself is aware of it.
- If you choose to import a hero from your previous kingdom to be the monarch of a new kingdom, the gossip about not being born in the country is actually true, but everyone would know it anyway.
- There is a quest called "Heir to the Throne", in which the monarch wants to have the perfect heir to the throne. It's completely pointless, as the Monarch can marry and have children at any time. It's purely for the funny. The Monarch must choose one out of three "suitors" to have the perfect baby with, and pick out traits he/she wants his/her child to have, and Hilarity Ensues.
Funny / The Sims Medieval