Cabin Boy
I know, I know... the plot is stupid, the effects are over the top, and some of the acting is horrific (lots of people mention Letterman's cameo here, but I think Melora Walters is far worse). But I can't help it! Chris Elliott cracks me up. Andy Richter as the idiot Kenny is amazing. ("This is how a harem girl dances.") And the rest of his crewmates aboard The Filthy Whore... Brion James, Brian Doyle-Murray, James Gammon... ahhh... love it.
I can't even claim to have developed an affinity for this movie before I would have known better. It came out when I was in college.
"We're just here to catch fish and stink."
"Mostly the latter."