Cabin Boy

Cabin Boy, is a bizarre fantasy film produced by Tim Burton, which starred comedian Chris Elliott. Elliott, cowrote the film with Adam Resnick. Both men worked for the "Late Night with David Letterman" TV show in the 1980s.

Warning: Wikipedia contains spoilers

Elliott plays a snobby "fancy lad" school boy named Nathanial Mayweather, who, upon graduation, mistakes the "Filthy Whore" for his millionaire father's yacht. Mayweather learns of his mistake only after the ship sets sale, so he is forced to do his best to convince the four filthy seamen to take him to Hawaii to be reunited with his father, played by Bob Elliott.

The crew (and accidental passenger) of the "Filthy whore" encounter a number of strange and disturbing beings including Chocki the man-shark.

The film includes a brief appearance from Elliott's former boss, David Letterman, as Earl Hofert, the crusty fishing village stuffed monkey salesman.