Captain Smirk is the sword trainer who teaches Guybrush the art of Insult Swordfighting in the first game and also provides him with a few starter insults. He lives in Captain Smirk's Big Body Pirate Gym at the East end of Mêlée Island.
He also has a history with the Swordmaster of Mêlée Island, having "fought side-by-side with Carla at Port Royal". Smirk is eventually convinced to train Guybrush due to his insistence that he indeed "does have what it takes". Though he says he likes Guybrush's spirit he later admits that he has no choice since LeChuck has scared off most of his normal clientèle.
The training method he used on Guybrush was a strange contraption known simply as "The Machine".
Smirk's appearance has some similarities with that of actor Arnold Schwarzenegger, such as being extremely muscle-bound with a buzz-cut and an ever-present cigar in his mouth. However, he also wears an eyepatch, his hair is white and he speaks like a military drill-sergeant rather than with an Austria-German accent.
- "Whaddaya want, maggot?"
- "Swordfighting is kinda like making love. It's not what you do but what you say what's important."
- The Secret of Monkey Island and Special Edition (first appearance)
- Escape from Monkey Island (mentioned only)
- Jarion Monroe (Special Edition)