The choices that have to be made.

I doubt if ppl will bother reading this - its not the smut that comes after the drabbles, unfortunately.
This is the part where I confess creative influences, and have a rando-babble about my thoughts on those influences.

Disclaimer - the Mouse owns all... Pirates, Officers & even monkeys.
Also - I confess. Fight Club inspired. Couldn't resist paraphrasing:

"You were looking for a way to change your life. You could not do this on your own. All the ways you wish you could be, that's me... I am smart, capable, and most importantly, I am free in all the ways that you are not." Tyler Durden.

Maybe it's just the side effect of Fight Club & PotC being almost the only DVDs I own, but I am seeing huge potential similarities between the relationship between Tyler Durden & the narrator, & Capt Jack & the bally Commodore. Jack *is* free in all the ways that James doesn't know how to be.

My take (warning - spoilers!)
Both James & the narrator are trapped in their chosen & self imposed roles, deluding themselves into believing they are close to being content & perfect. Repressed & depressed, & it's self imposed! All they really want is to be free, & to get the girl, but are too repressed to properly do anything either, & someone else gets the girl. A charismatic and eccentric man enters their life, who they can't help but feel drawn to, because they recognise the potential that man has to liberate them from their lives, by destroying that which keeps them from being free. Jack & James will be simulataneously happy & frustrated by chasing round each other, but would not be happy if the game ended. I say, never be content. I say, never me be complete. Deliver me Tyler, from being perfect and complete. And just like with Tyler, if James were to spend too much time with Jack, things would probably get too far out of hand. But of course, some part part of him wants that. And I think he'd be a more complete person after Jack's liberating influence. Probably too late to get the girl - Elizabeth isn't anywhere near as tolerant as Marla. And she already has her good man/pirate mix. But the one day's head start comment - it's the first sign of real humour from James, and its because Jack helped him let go of a small bit of repression, by example.

Jack's style of planning, & a lot of his philosophy on life, is *really* similar to Tyler's. They are not bound by the same rules as the rest of the sheep. Both become surrounded by a reputation that is rather embellished, and want to live forever in infamy. They both love their mischief, and swordplay/fistfights. Both very eloquent, in their own way.

"You had to give it to him: he had a plan. And it started to make sense, in a Tyler sort of way. No fear. No distractions. The ability to let that which does not matter truly slide." This realisation is very similar to Will's when he saw Jack pocket the coin.
"I'll bring us through this. As always. I'll carry you - kicking and screaming - and in the end you'll thank me." Jack's approach to Will. Pity he got an oar in the back of his head for his troubles.

Of course, there are limitations. When Jack & Tyler leave, James and the narrator chases after them, with little idea of what to do once they have caught him, but being unable not to. We're assuming that James' father didn't bail, & he was raised under a strict moral code, not to mention Naval training. As such, he doesn't have the "courage to run with it" as the narrator did, or possibly just the sheer desperation. Give him a few months of making nice in polite society where he has to see Will & Liz looking cute & happy, & then maybe. As well as a stricter moral code, James also has more compassion than the narrator ever had. And Tyler's anti-materialistic stance doesn't exactly mesh with Jack's greedy streak, although he is a pirate with enough depth to recognise that "not all treasure is silver and gold." And Tyler is of course rather more ambitious than Jack, as "the goal of Project Mayhem was the complete and right away destruction of civilisation" whereas Jack is more content just to poke fun at polite society. All Jack really wants is the Pearl & his freedom. And of course, there is the slight difference that Jack is actually real, well, as real as a fictional character can get. In other words, he's not a figment of James's imagination or a dissociated personality.

Still, it's an interesting thought. Plus, of course, the UST runs very clearly through both movies.