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Cabin Boy is a 1994 American fantasy comedy film, directed by Adam Resnick and co-produced by Tim Burton, which starred comedian Chris Elliott. Elliott co-wrote the film with Resnick. Both Elliott and Resnick worked for Late Night with David Letterman in the 1980s as well as co-creating the Fox sitcom Get a Life in the early 1990s.

Plot

Nathaniel Mayweather (Chris Elliott) is a snobbish, self-centered, arrogant, despicable, loathsome virginal man. After graduation, he is invited by his father to sail to Hawaii aboard the Queen Catherine. After annoying the limo 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 (Andy Richter). He thinks the ship, The Filthy Whore, is a theme boat. It is not until the next morning that Captain Greybar (Ritch Brinkley) 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 weird events occur. The ship is caught in a fierce storm and Kenny is knocked overboard and drowns. 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, more mature, person. With only one island in the entire area, the crew decide to set sail there.