Monkey Island

Probably the best modern day comedies about pirates are the first two Monkey Island computer games: Secret Of Monkey Island and Monkey Island II: LeChuck's Revenge.

The later games were written by different people and may not be as good (I haven't played them), but the first two are absolutely excellent as sources of pirate humour. They're not exactly historical, but they show how to get the maximum amount of jokes from the setting.

You should be able to pick them up fairly cheaply on ebay etc, or alternatively watch some of the walkthroughs of these games on YouTube so you can see the whole plot.

(This isn't a historical fact, but my favourite joke from the MI games were the pirates who tried to buy a glass-bottomed boat, but when they set sail it turned out to just be a normal boat with the hull removed.)

Mythbusters "Pirate Special"

In the popular TV show MythBusters (Myytinmurtajat in Finnish) the crew performs experiments to verify or debunk urban legends, old wives' tales, and the like.

In the special pirate myth episodes, they try to replicate pirate myths to find out if they are true or not.
In the first pirate special they covered the myths:
-The effectiveness of canon ball impact debris vs the ball itself against pirates
-Will wearing an eye patch in one eye preserve night vision
-Can a person can safely slow a fall by using a knife to cut a sail
-Pirates used rum as a means of cleaning clothes in addition to drinking it
http://mythbustersresults.com/epsode71

The second pirate special had a lot of myths mostly involving firing improvized ammunition out of an old cannon. http://mythbustersresults.com/episode92

Some clips from those episodes are also available in Youtube http://www.youtube.com/results?search_query=mythbusters+pirate

Pirates info

Don't worry, I'm from the Internet.

This time we have the pirates info page, with wikis about pirate history, pirates, links to books and media... and what do you know.. a pirate community :)

http://www.piratesinfo.com/

Pierre Le Grand

Another of my favourite pirate stories. (It's from Exquemelin's Buccaneers of America, not the most reliable of sources, but what the hey. http://en.wikipedia.org/wiki/Alexandre_Exquemelin) Le Grand and 28 men, sailing in a tiny boat, sighted a Spanish galleon and pursued it. Using their smaller vessel's greater agility, they deftly approached the galleon from the stern side (where there were no guns - a single broadside could've torn their boat to shreds). In a triumph of attitude over caution, Le Grand scuttled the boat so that they had to succeed or die trying. They took the gun room - cutting the sailors off from their small arms - and surprised the Spanish captain in his cabin, playing cards. The Spaniards were forced to surrender.

Libertalia

Pirates and buccaneers are a subject very close to my heart, and one of my favourite details about them is the (probably) fictional utopia called Libertalia (http://en.wikipedia.org/wiki/Libertalia). It sounds like a nice place to live in.
Now, what IS actual fact is that 17th-century buccaneers were a pretty democratic lot for their time. (I disdain the more famous 18th-century pirates, who were nothing more than sociopathic criminals.) Their captains were elected, loot was fairly shared, and they had what might be termed the first health insurance in existence, in that they often had predetermined compensations for those injured in action. See http://en.wikipedia.org/wiki/Pirate_code.

Pirate ships found

Here are a couple of interesting articles about Blackbeard's and Kidd's ships:
Blackbeard’s ship is to be fully excavated. The notorious pirate’s vessel ran aground off North Carolina’s coast in 1718.
http://www.msnbc.msn.com/id/17434128/

Also the wreckage of Captain Kidd's ship was found
http://www.msnbc.msn.com/id/22247690/

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p.s. One of the first computer games I was seriously hooked on was Pirates! on C64. Oh man, I raided the Caribbean :)

Arrgh here be poirates, meee heartys

The swash buckling pirates we see on the tv and recently at the movies are fine and dandy, but historically they were only around for 20 or so years.

Sure there have been other pirates since the time people could float on water.

If you want to have modern pencil pushers turning to a life of "Arrgh me heartys", maybe they could have a pirate bible, that naturally would be incomplete historically and be entirely romantic in its ideals e.g. the Pirate code etc. etc.

Mythbusters did a Pirate special, and the eyepatch thing turned out to be a plausible night fighting technique.

One Piece is the closest cartoon you will come to that is Pirates in a pseudo modern setting.