When the 1994 movie Cabin Boy opens, Nathaniel Mayweather is wrapping up his stint at a posh finishing school for wealthy young men, a snobby jerk in shorts and powdered wig, his father's vast hotel fortune earning him a place in the world as a Fancy Lad. Nathaniel, given slothful life by the slouching, hilariously idiotic Chris Elliott, is pretty much a douche to everyone, from his fellow students to the headmaster to the driver of his father's limo. (By way of example - while the stuffy headmaster is admonishing him to be less of an a-hole, Nathaniel sardonically wonders aloud what drifter's corpse the man stole his shoes from. You get the idea.)
Things change for pampered, prissy Nathaniel when he takes a wrong turn looking for the yacht that will take him to Hawaii and cossetted employment with the family empire. With help from David Letterman in an uncredited cameo as a salty villager, he winds up on board the Filthy Whore, a working-class fishing boat full of grimy, drunken, vulgar sea dogs. Hilarity ensues, much of it bizarre and confusing, as Nathaniel tries to convince the crew to take him to Hawaii. Along the way he rescues/abducts a young woman, Trina, trying to set the world record by swimming from Maryland to Maryland, and he falls in love with her, though she rejects his advances. The film really goes off the rails as the crew advise Nathaniel to visit a six-armed woman on a remote isle who will turn him from a Cabin Boy into a Cabin Man. (He succeeds in this quest, after which he emerges from her mountaintop cave with the stirring declaration, "These pipes...are clean!!!") Trina swiftly changes her mind about Nathaniel, his sexual awakening serving as the catalyst to shed his sophomoric doofiness.
It's a silly movie, disjointed and at times clumsy. But it's a perfect vehicle for Elliott's comedic style, self-deprecating and yet caustically insulting, and the supporting cast of fishermen builds an ideal team of tormentors for the Fancy Lad. The key is that the film makes no pretension to being more than an extended vaudeville skit based on a thin premise. And yet, at times it reaches for scathing commentary on ludicrous film tropes and succeeds - the rapidity with which Trina falls for him after his loss of virginity is laced with dialogue so patently aware of its own foolishness. There's a meta-awareness to Cabin Boy, a sense of how stupid it all is. I haven't even mentioned Chocki the shark-man or Kenny, David Richter's developmentally delayed crewman. Watch it, if you can stand it. You'll laugh despite yourself.