Hector Barbossa could be Boba Fett

Connections:
- - Both serve as an infamous rival to the 'Captain'.
- - Both are part of the pirate world.
- - Both wear legendary headgear.
- - Both are portrayed as antagonists but are well alright really.
Governor Swann could be Grand Moff Tarkin

Connections:
- - Both are 'extremely British'.
- - Both have influence with the powers that be.
- - Both have minimal yet important roles.
Mercer could be Admiral Piett

Connections:
- - Both were unquestionably loyal to their Empire.
- - Both take command of their respective ship when their superior is murdered.
- - Both are diving experts.
Sao Feng could be Jabba the Hutt

Connections:
- - Both are introduced late in the trilogy but serve as a major character.
- - Both are powerful Pirate Lords.
- - Both serve as a neutral force in the over-arcing war.
- - Both of them have a problem with the 'Captain'.
- - Both live in a lair full of freaks and monstrosities.
Tai Huang could be Bib Fortuna

Connections:
- - Both serve a Pirate Lord.
- - Both have the same accent and are excessively sweaty.
- - Both are easily swayed.
Leech could be Greedo

Connections:
- - Both are dislikeable wankers.
- - No one cared if they lived or died.
- - Both were foolish to cross the 'Captain'.
Lt. Gilette could be Lobot

Connections:
- - Both serve as a loyal follower of the 'Traitor'.
- - Both have a minimal yet noticeable role.
Lt. Groves could be Nien Nunb

Connections:
- - Both aren't afraid to say what they are thinking.
- - Both worked closely with the 'Traitor' during the story.
The Kraken could be The Sarlacc

Connections:
- - Both were creatures with industrious appetites.
- - Both had many tentacles and a beak.
- - Both live in a 'sea'.
- - Although they ate living organisms, this doesn't always result in death.
Captain Teague could be Admiral Ackbar

Connections:
- - Both are extremely respected individuals and great ship Captains.
- - Both were prisoners who managed to escape.
- - Quote machines.
The Brethren Court could be Rebel Command
  
  
  
 
Connections:
- - They were all privileged, important individuals forced out by a tyrannical Empire as they didn't agree with the way the 'world' was going.
- - Both are leading a group against a force with more resources, manpower and weaponry.
- - Both live outside of the law and are on the run.
The Dutchman Crew could be The Imperial Officers
   
  
Connections:
- - Fiercely loyal to their cruel, murderous Commander.
- - All cannot leave their position due to fear and obligation.
- - Served as supporting villains in the second installment.
The Cursed Crew could be The Bounty Hunters
   
  
Connections:
- - All are part of the pirate world and care mostly for money.
- - All are only loyal to themselves.
- - All strike fear into their enemies due to their abilities.
Scarlett & Giselle could be Oola & Jabba's Dancers
 

Connections:
- - They all serve as totty.
Anamaria could be Mara Jade

Connections:
- - Both are strong-willed women.
- - Both don't reveal their identity straight away.
- - Both have a minor but resonating role in the over-arcing story.
Jack the Monkey could be Salacious Crumb

Connections:
- - Both are a species of monkey.
- - Comic relief.
- - Immortal.
The Prison Dog could be Wedge Antilles

Connections:
- - Both managed to survive insurmountable odds several times.
- - Omnipresent and possibly Immortal.
Comments
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Description
I know we've all heard it but I thought I'd use the facilities of Listal to accentuate the point.
Since Pirates of the Caribbean: Dead Man's Chest was released, everyone with access to a column or blog has noted the very similar plot and character traits with the Star Wars original trilogy, notably Star Wars: The Empire Strikes Back. This is my take on this comparison.
Have fun.
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The biggest stretch is definitely Anamaria.
Thanks for all the votes guys.