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Insult sword fighting is a concept first introduced in The Secret of Monkey Island. The idea behind insult sword fighting is not about having the sharpest sword; it is about having the sharpest wit. To start, one pirate opens with a line, such as, "People fall at my feet when they see me coming." The opponent then must retort with something that makes sense, such as, "Even before they smell your breath?" However, a nonsensical response ("How appropriate. You fight like a cow.") will cause the "defending" pirate to lose the round. A pirate that wins three rounds consecutively (either defending or attacking) wins the fight.
Guybrush Threepwood, the protagonist of the Monkey Island series, must master insult sword fighting in order to complete the three trials to become a pirate. He is trained by the sword master Captain Smirk, and then must defeat the sword master Carla. Carla is so good at insult sword fighting that the player can't insult, only retort. This happens again in the Curse of Monkey Island while facing Captain Rottingham. In Escape for Monkey Island the player faces Ozzie Mandrill, but due to his thick Australian accent and gratuitous use of Australian slang it is impossible to defeat him.
Land-based insult sword fighting is pretty straight forward, but on the sea the rules change. When insult sword fighting outbreaks on a boat at sea the retorts must rhyme with the insults, as well as make sense. For example the correct response to "You're as repulsive as a monkey in a negligé" is "I look that much like your fiancee." An incorrect retort would be "Oh that is so cliché."
Variations of Insult Sword Fighting
While Guybrush Threepwood embarked on his honeymoon, insult swordfighting underwent a paradigm shift. Now insults can be flung while arm wrestling and playing darts, though the latter is not seen on screen, only mentioned.