Pirates of the Caribbean was a D&D Adventure

Here's my theory: Pirates of the Caribbean was a one-shot put together by a Dungeon Master who was between regular D&D games. It was based on the Disneyland ride and meant to be a throwaway game with a swashbuckling theme.
There were three players, one was an old D&D veteran, and the others were new to roleplaying games in general. In fact, Elizabeth Swan's player was likely a girlfriend who had always heard about this kind of game and decided to give it a shot.

Elizabeth's player (Liz) was dating Will Turner's player (Bill). Liz was a big fan of all things Jane Austen, and so made her character be the daughter of the governor.

Bill had played once or twice. This guy was an engineer in real life, but not especially creative. He decided he wanted to be a blacksmith from a port town (Tortuga). We see him applying his real-life engineering knowledge when we hear Will talk about half-barrel pin hinges on the prison door.
 

Jack Sparrow's player (Jake), meanwhile, is a veteran of D&D, and has a great sense of humor. He maxes out his Luck and Agility stats at the cost of everything else. He decides to make a legendary pirate, even though he's not a very good one.

Since it's a one-shot adventure, nobody worries about their backstory, least of all Jake.

Curse of the Black Pearl

The first adventure was cobbled together by the GM in just a few hours. He wanted to hit all of the classic pirate tropes, including cursed treasure and zombie pirates. He found a way to hook in Bill's character by making him the son of a pirate involved with Barbossa's gang. Jack Sparrow is the marooned ex-captain of the crew, and finally, Elizabeth just gets roped in because of a mix-up.
 

Jack Sparrow never really fights. Whenever faced with combat, he concocts elaborate schemes and situations that let him skirt danger without harm. It's what his character was meant for; escaping peril.
 

Will is a bog-standard fighter, and once again, Bill isn't terribly creative, so tends to swing his sword when trouble comes along.


Liz is only in it for the roleplaying, and often finds herself captured or otherwise incapacitated, which is a little sexist, but then again, Liz doesn't really take much initiative, so it's the only way the GM can get her involved.

The session goes so well that the players want to keep playing. Unfortunately, they don't meet up for over a year.

During that year, the GM posts the adventure summary on his blog and it goes viral. People really like the adventure, and people start giving him suggestions. The GM gets inside his own head a bit and plots out a huge, detailed world, involving ancient sea gods, Pirate Kings, obscure ocean legends, and detailed character arcs. He makes up several GMPCs. He spends the whole year hyping up the next adventure on his blog. That Christmas, when everyone is together again, he busts out the next adventure.

Find out what happens in part 2.