J is for the Jolly Roger

[This is the 10th of my April A-Z Challenge series of posts on Symbols, Glyphs, and Sigils. Each day I'll try to include some material that old-school role-playing gamers will find useful, but I can't guarantee that there won't also just be a few posts filled with weirdness for the sake of weirdness....]

Well, I can't wait until September 19 -- or even for the letter "Arrrrr" later this month -- so today will just have to be about pirates.

Blackbeard's favorite version

In the 1600s and 1700s, most pirates just flew a pure black flag, but others added the skull and crossbones or other scary signs of death and dismemberment (including more subtle memento mori such as an hourglass) to frighten their victims into surrendering without a fight.  Nobody knows for sure where the name "Jolly Roger" comes from, but many believe it's a derivative of the French joli rouge (pretty red), for the blood-red versions of the flag that were sometimes flown.

Pirates are often stock non-player characters in many kinds of fantasy adventure games. However, often people just look to the classics (from Treasure Island to Jack Sparrow) and make their pirates pretty stereotypical.  Fun as that can be, here's a random table to throw a monkey-wrench into those bog-standard pirate tropes...

Our Pirates Are Different:  Roll d20 for Freebooter-Themed Foibles

1. The captain has a strange psychological quirk.  There are plenty of quirk/flaw lists out there... try Mike Monaco's modification of Galloway's classic Bogey Table.
2. The captain has a strange magical anomaly.  Roll 1d20 on Dyson Logos' table of unusual characteristics for pirates from last year's April A-Z.
3. The captain is powerless.  He or she is secretly the puppet of another (random) crewmember.  Is it magical coercion?  Or just good old blackmail?
4. The captain is a stereotypical Long John Silver type, but the crew is all made up of people from a very different part of the world.  How did these folks get together?
5. The captain is a woman.  No... scratch that.  The "pirate queen" trope is getting pretty stereotypical, too.  How about a pirate Red Queen?
6. The crew are all lycanthropes.  When is that next full moon?
7. The captain and crew are all devotees of a strange deity unknown to the PCs.  Will they try to convert the PCs?  Or sacrifice them?
8. A seemingly innocent cabin boy is planning mutiny.  He has almost half of the crew on his side.  (The captain killed his parents...)
9. The crew has a good luck charm that they believe keeps them safe in battle.  It's displayed out in plain sight, but it's taboo to talk about it too much or touch it disrespectfully.  Hopefully it's nice and shiny, so one of the PCs won't think anything of picking it up, tossing it around, and saying "Hey, what's this?"
10. Down below, the crew keep a powerful druid prisoner and force him (with a stolen Ring of Human Influence) to constantly cast Control Weather to give the ship good seas.
11. The captain and crew are wanted... not by the authorities, but by all other active pirates in the area for breaking an article of the Pirate Code.  Preferably one that is fairly incomprehensible to the PCs!
12. The crew is divided into several (four? five?) warring factions.  Everyone is out to get everyone else, but they're so cagey and shrewd no direct hostilities are ever carried out.
13. The pirate ship is a strange color, and/or has sails with strange things painted on them.  Who's the on-board artiste?
14. At night, nobody goes below.  At the last port of call a random monster scurried aboard, and the ship cast off without knowing.  It's killed several crew members already, and it makes sounds that chill you to the bone, me hearties... but it never comes up into the open air...
15. The ship was captured from the local navy and still looks very much like a ship of the line.  ("So, is this the new Bluesmobile or what?")
16. The ship still drags about a dozen corpses from a recent keelhauling.
17. The ship is haunted.  Not a semi-ghostly curse like the Flying Dutchman, but it's literally haunted by the spirits of people killed by the captain and/or crew.  Will these ghosts eventually become numerous (powerful) enough to sabotage the ship, or attack crewmembers directly?
18. Once per day, the ship can magically go underwater for 30 minutes of super-cool submarine attack action...
19. The ship is equipped with the equivalent of stinkpot projectiles (adjust tech level to be era-appropriate).  And they literally stink, too.  Well, how else do you expect them to efficiently get rid of the contents of their... poop deck?  :-)
20. Roll another d20 for more randomness "At Sea in the Tropics."  See pages 61-62 of the 2011 Secret Santicore, and combine the sub-tables titled SHIPS and CREEPY.

Once your quirks are known, use this to name the ship, use this to name some of the pirates, and you're ready to cast off!