Curse Of The Black Pearl ( 1729, age 39 )

Our introduction to Jack Sparrow is as iconic as the man himself. Bailing out a sinking ship, he realizes the cause is lost and rather than panicing or abandoning ship, he climbs to the highest point and lets nature take its course, timing his own entrance with remarkable flare for one whose ship had just been lost.

Within the first minute we learn that he has a penchant for dramatics, is charming with his words, and is capable of deducing means to his ends without any loss ( noting the coin purse, paying for no questions asked, and making profit from it in so doing! )

Jack lies by telling the truth. His honesty is baffling, his words remarkably educated and dizzying in logic that is always steps ahead of everyone around him. A pirate with a bullet he will not fire, who speaks of the idea that those who are pirates can be good men, who looks at a ship not as ropes and sails and hulls but as freedom – this is the man Jack has grown to become through all of his trials.

He is a pirate of convenience still, owning it only when it suits him and brushing it aside whenever it does not. The Lord of the Caribbean, though we don’t know it yet, comports himself uniquely in the fact he is not obsessed with treasure or pillage, but adventure and freedom. He lacks fear of the supernatural in a remarkable manner that reflects well on the past of one who has seen it around every corner.

He is a masterful manipulator, which is to his credit and his bane – people consistently refuse to trust him on account of the fact he is a pirate, and on account of knowing nothing of who he truly is. He is not one who would sacrifice life – he preserves it at every turn and opportunity – and he is an unmitigated genius. Yet the prejudice of the past is not lifted – Jack’s genius is seen as madness, he is seen as daft – and his habit of saving people continues to be something that damns him rather than granting any sort of reprieve.

By the end of the film, Will Turner has a higher kill count than Jack Sparrow, a pirate of some thirty years, as with Barbossa he brings his number of intentional dead to two. ( More on this in the salt that is DMTNT. )