I put this matchup to my friends and the decision was very one sided.
Scenario 1:
Captain Sparrow draws his sword. Captain Hook draws his gun and shoots Sparrow dead.
Scenario 2:
Captain Sparrow is immortal. Captain Hook keeps stabbing him, gets frustrated and puts him in the Boo Box, leaving him to be stung by scorpions forever.
Scenario 3:
The Black Pearl is manned by a rag tag crew of comic relief. The Jolly Roger is manned by a rag tag crew of former Lost Boys who now spend all day slitting the throats of child guerrillas and a magic flying elf, showing both cruelty and proficiency. The Pearl is sunk.
Scenario 4:
The Jolly Roger is the same. The Black Pearl is manned by the fearsome zombie crew.
"Heh. We're going to need a lot of Boo Boxes." - Hook
The zombie crew is the only way the Pearl has a chance, but remember that's twenty zombies versus (from the movie Hook) a CITY of cutthroats.
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