Recent Fancy Lad graduate, Nathaniel Mayweather (Chris Elliott) is meant to set sail aboard the Queen Catherine to Hawaii but since he can't stop being a huge dick to everyone he gets stranded and walks in the wrong direction to a small fishing village where Old Man, David Letterman sends him to board the Filthy Whore.

After he dupes simple Kenny (Andy Richter) he manages to stowaway and wakes to a drunken, stinkin' crew - Skunk (Brian Doyle Murray), Big Teddy (Brion James), Paps (James Gammon) and Captain Greybar (Ritch Brinkley) who are all now lost at sea. When Kenny goes overboard, the crew forces Nathaniel to take his place on the way thru Hell's Bucket where he draws the attention of the shark man, Chocki (Russ Tamblyn), plucks swimmer Trina (Melora Walters) out of the ocean and gets his pipes cleaned at Callies (Ann Magnuson).

Hopefully they can get off this cursed island before Callie's husband Mulligan gets to them in Cabin Boy, this week on Doom Generation.