Roger de Flor.

Born in 1267 in Siciliy. It was an interesting time, the crusades, italian city states, mercenaries and the renaisance. He served on a galley belonging to the knights templar at a young age and eventually rose to become it's captain. After rescuing wealthy survivors from a city seiged by the Islamic caliphate Deflor was denounced by the Pope for robbery and personal disputes. DeFlor then fled and began pirating.

He rose to prominence and came into the service of the Sicilian King who was at war with Naples. After the war a group of now unwanted mercenaries hired by Siciliy was left idle. The Sicilian King gave De Flor a fleet of ships and a title of vice-admiral so he could take the mercenaries away. DeFlor did and created the Catalan company/mercenaries. They sailed to Byzantine Constantinople where they were at war with the Turks. The Byzantine emeror grateful for any help, gave DeFlor his neice up for marriage and titled DeFlor Duke. DeFlor and his mercenaries drove away the Turks. The Byzantiums wary of DeFlors rise in power decided to betray DeFlor and his company. They were repulsed and DeFlor rode back to Consatninople to demand payment. The Emperor gave DeFlor the title of Ceasar and then the Emperors son assasinated DeFlor. The Catalan company began to disperese and in revenge pillaged and plunder their way throughout the Byzantine Empire.

Probably more of a tv show than a movie.

Oh and I'd love to see Ching Shih. A Chinese female prostitute in the 1700s who rose to become a pirate queen commanding hundreds of ships and tens of thousands of men. She challenged empires, the portuguese, british and Chinese. She was given a pardon by China and eneed up retiring with her wealth and opened a gambling shop.