"Fancy Lad" Nathaniel Mayweather is due to graduate from board school, after which he will return home to take over the family business. On his way to the docks to ride an ocean liner home to Hawaii, Nathaniel's bad attitude upsets the limo driver, who promptly throws Nathaniel out. Walking to the docks by foot, his naive yet arrogant nature leads him to an old fishing oat at port, where its mentally challenged cabin boy Kenny(Andy Richter) lets Nathaniel on board. Discovered by a very angry crew the next morning, the fancy lad is abused & insulted until he tricks Kenny into plotting a course for Hawaii... unfortunately this course leads directly through a haunted area of sea known as Hell's Bucket, upon where Kenny is thrown overboard and the crew make Nathaniel their new cabin boy as punishment. That's assuming they survive Hell's Bucket.
- Accordion to Most Sailors: Captain Graybeard plays a concertina at several points throughout the film, including when the crew pelt Nathaniel with beer cans for entertainment.
- Anachronism Stew: Nathaniel Mayweather is attending a boarding school that looks like it is out of 1800's Britain, complete with powdered wigs. A modern limousine exists, yet long distance travel is still by ocean liner. The Filthy Whore has antique fishing equipment yet also has a microwave thrown in randomly.
- The Cabin Boy: A foppish "Fancy Lad" mistakenly boards a fishing boat ran by filthy, foul-mouthed sailors who make him their cabin boy.
- The Cameo: David Letterman appears in one scene as the "Old Salt in the Fishing Village", credited under the pseudonym Earl Hofert (which was Letterman's maternal grandfather's name).
- Half-Human Hybrid: Chockie, who is said to be "half man, half shark".
- Living Figurehead: The figurehead of the Filthy Whore(played by Ricki Lake) is animate, rolling her eyes at one of Nathaniel's lame jokes, having a frightened expression when sailing into a storm, and growing a beard when they sail through Hell's Bucket.
- Non Sequitur Environment: Hell's Bucket in a nutshell; when the crew go to sleep, the temperature is nearly tropical, and the next morning they're awakened by an iceberg crashing into their ship.
- Ocean Madness: When Nathaniel is left on a raft alone he not only drinks the seawater but sees a tobacco spitting, foul mouthed floating cupcake.
- Seadog Beard: Some impressive ones.◊
- Sex as Rite-of-Passage: Nathaniel visiting Calli is this. He comes out of her cave with gusto.
- Unsympathetic Comedy Protagonist: Nathaniel starts out as one - he spends most of the first third of the movie as a self-centered snob who condescends to pretty much everyone he meets, so that any subsequent misfortune or humiliation he receives is seen as comeuppance. As he starts getting a bit of Character Development, the humor starts being more about his being a naive City Mouse instead.
- Upper-Class Twit