Image pinched from Amazon's page on Cabin Boy where you can pick it up for the bargain price of $9.99!
Today is "Talk Like a Pirate Day" and, once again, I recommend everyone avail themselves of this opportunity to act a bit stranger than usual. Last year, I made some celebratory recommendations. This year, I've got a few more.
First off, I'm going to watch "Cabin Boy" and I recommend you consider doing so as well. While it isn't actually about pirates, it does contain obnoxious salty dogs and is incredibly goofy. That's about 80% of what being a pirate is all about. Chris Elliot does his usual somewhat weird (and sad but not too sad to undermine the fun) man-child routine to very good effect here. It also contains a classic (and rare big screen) David Letterman moment. A snippet of Dave's short scene was parodied in his one-time-only hosting of the Oscars and I wish I could find a link to YouTube showing it or had already digitized it myself as it's probably the shining moment from that particular Oscars extravaganza.
A lot of people don't "get" Cabin Boy's humor. It helps if you've watched any of the old Dynamation movies from the 60's as it plays on a lot of the concepts in movies like Jason and the Argonauts or the Seventh Voyage of Sinbad. It twists the characters like the cyclops and other giant monsters comedically. If you can't get into the spirit of this sort of parody, then probably you won't enjoy Cabin Boy. It also helps if you've ever played any of the Monkey Island games since it's about as close to a live action version of the games as we're likely to ever see. Chris Elliot is a lot like Guybrush Threepwood though quite a bit more arrogant.
(And finally) Arrr, if you can't talk like a pirate and need some remedial trainin', Me recommend you go har for a translation.