Cabin Boy (1994)

Synopsis
Former NBC intern and Get a Life creator Chris Elliott stars as the title character, a recent graduate of the exclusive Fancy Lad Academy who unwittingly boards the wrong sea vessel and ends up a whipping post for its gruff, foul-mouthed crew after his predecessor (Andy Richter of The Late Show) falls overboard. Over the course of their adventures, Elliot eventually earns the respect of the crew as he also earns his manhood. This supremely silly film features sight gags and tastelessness galore, including a love scene with a woman who's all hands -- literally. Elliot's old boss David Letterman appears in an amusing unbilled cameo as a sarcastic villager in port. In all, Cabin Boy works much in the same vein as Elliot's former TV show; a crass sense of humor is helpful for full appreciation. ~ Jeremy Beday, All Movie Guide