Funny / Sid Meier's Pirates!

• Once you've defeated some of the low-ranking pirates in the 2004 version, the more experienced ones get savvy to your Finishing Move with the crate. Some of them will duck, only to be caught on the backswing; and the last and best will leap up onto the crate, waving his sword in taunting triumph... only to accidentally cut the rope himself.
• Things can get strange if you're trying to do the main quest while staying on good terms with the Spanish since the recurring villains are all of that nationality and tend to stick to Spanish towns. In one memorable write-up, a player tells of going to see the Governor of Havana, only to find him in tears: it seems that his beautiful daughter, whom the player has been courting, has been kidnapped. Her captor, the evil Mendoza, was last seen in Havana.
  "But your Excellency... this is Havana."
  (sadly) "Sí."
  • After a short walk to the cantina and an even shorter duel, father and daughter were joyfully reunited.
  • It gets even stranger when you have to attack Mendoza while he's on his Fast Galleon. After defeating the obviously evil Mendoza and returning to port, you'll be praised for rescuing the governor's daughter... and then scolded for attacking a Spanish Fast Galleon.
• Turning down a Governor's request to rescue their kidnapped daughter results in said governor fainting dramatically before regaining their composure.
• Just the fact that, despite that you're playing in an era centuries before the advent of cosmetic surgery, every single barmaid you encounter has massive breasts.
• If you make a mistake during the dance, the governor has a belly laugh at your expense.
• A random stranger in the corner of a tavern claims to have information about your long-lost family member that he will gladly share with you... for 1,000 gold pieces. Who does that?
• Every barkeep is obsessed with where to find beautiful governors' daughters. Funny, yes, but also creepy.