Nathaniel Mayweather is a snobbish, self-centered, arrogant, virginal "fancy-lad." After graduation, he is invited by his father to sail to Hawaii aboard The Queen Catherine. After annoying the limousine driver who is taking him to board the boat, he is forced to walk the rest of the way.

Nathaniel makes a wrong turn into a small fishing village where he meets the imbecilic cabin boy/first mate Kenny of The Filthy Whore, which Nathaniel believes to be The Queen Catherine as part of a theme. The next morning, Captain Greybar finds Nathaniel in his room and explains that the boat will not return to dry land for three months. Nathaniel unsuccessfully tries to convince each fisherman to set sail to Hawaii, but convinces Kenny into doing so. However, the crew reaches Hell's Bucket, a Bermuda Triangle-like area where strange events occur. The ship is caught in a fierce storm and Kenny is knocked overboard and drowns. With only one island in the entire area, the crew decide to set sail there. Without a cabin boy, Greybar forces Nathaniel to do the chores in return for taking him to Hawaii, as well as teaching him how to become a better person.

After failing all the chores he is assigned, the fishermen decide to give Nathaniel another chore that involves dragging him on a floating raft for a week. Nathaniel quickly runs out of supplies, begins consuming salt water, and suffers extreme sunburn after confusing cooking oil as lotion. He also realizes he might be going insane after sighting Kenny's ghost and seeing a floating cupcake that spits tobacco. After falling into the water he is saved by a shark-man. After nine days, Nathaniel is pulled back in and tells what happened. It is revealed by Skunk and Big Teddy that the shark-man is known as Chocki, the offspring of a male viking and female shark.

Nathaniel spots a beautiful young woman named Trina swimming in the ocean. After she is pulled up in a net, Nathaniel becomes smitten with her. Not pleased with another passenger on board, the fishermen decide to strand Trina and Nathaniel on the island they're sailing toward. Finally reaching the island, the crew searches for components to fix their boat. Nathaniel tries to get closer to Trina, who constantly rejects him.

Greybar and Skunk suggest to Nathaniel that a blue-skinned, six-armed woman named Calli can help build his confidence. After an encounter with Calli that results in his first sexual experience, Nathaniel again meets Trina, who becomes attracted to him immediately. Calli's husband Mulligan, a giant, comes home to find a man's bag. Realizing what Calli has done, Mulligan decides to find her lover and kill him. Nathaniel tries to save everyone by confessing to the giant he's the one who slept with Calli. Mulligan is about to kill Nathaniel with a giant nail clipper when Chocki saves him. Nathaniel then kills Mulligan by choking him with his own belt.

Finally reaching Hawaii, Nathaniel offers his newfound companions a job at the hotel where his father is the owner, which they refuse. They tell Nathaniel he's a fancy lad who should stay in Hawaii with his dad where he belongs. Nathaniel and the fishermen part ways, including Trina. His equally-snobbish father, William Mayweather, condemns his son's actions. Seeing through his father how snobbish he used to be before boarding The Filthy Whore, Nathaniel discards his wig and leaves to find Trina. They then both join the crew on The Filthy Whore.

• Chris Elliott as Nathaniel Mayweather
• Ritch Brinkley as Captain Greybar
• Brian Doyle-Murray as Skunk
• James Gammon as Pappy
• Brion James as Teddy "Big Teddy"
• Melora Walters as Trina
• Ann Magnuson as Calli
• Russ Tamblyn as Chocki
• Ricki Lake as Figurehead
• Andy Richter as Kenny
• Mike Starr as Mulligan the Giant
• I.M. Hobson as Headmaster Timmons
• Alex Nevil as Thomas
• David Sterry as Lance
• Bob Elliott as William Mayweather
• Edward Flotard as Limo Driver
• Jim Cummings as the Floating Cupcake (voice)
• Earl Hofert as Old Salt in Fishing Village

The project was originally to be directed by Burton, who had contacted Chris Elliott after seeing Get a Life. Resnick took over after Burton was offered the film Ed Wood.^[1]

The film received mixed reviews from critics. On Rotten Tomatoes, it has a 48% rating based on reviews from 27 critics, with a weighted average of 5.2/10.^[2]

Chris Elliott earned a Razzie Award nomination for Worst New Star, but lost to Anna Nicole Smith for Naked Gun 33+1⁄3: The Final Insult.^[3][4] The film was nominated for Worst Picture at the 1994 Stinkers Bad Movie Awards but lost to North.

Year-end lists edit

• 1st worst – Bob Strauss, Los Angeles Daily News^[5]

Hip hop producer Dan "the Automator" Nakamura named his publishing company, Sharkman Music, after the film.^[6] References to the film have appeared in multiple works by Nakamura.^[6] For example, the Bulk Recordings edition of Kool Keith's debut solo album Dr. Octagonecologyst, contains a dialogue excerpt from the film preceding the song "halfsharkalligatorhalfman"; the hook of the song, "Half Man, Half Shark", is sampled from the same dialogue.^[7]

Post-hardcore band A Static Lullaby reference the film in their song "Half Man, Half Shark; Equals One Complete Gentleman", the title of which is a paraphrase of an Elliott line spoken in the film.^{[citation needed]} The song can be found on their Faso Latido album.

• Cabin Boy at IMDb  
• Cabin Boy at Metacritic  
• Cabin Boy at Box Office Mojo
• Cabin Boy at AllMovie
• Cabin Boy at the TCM Movie Database
• Cabin Boy at the American Film Institute Catalog
• Cabin Boy at Rotten Tomatoes