DOUGLAS FAIRBANKS AS THE BLACK PIRATE - THE BLACK PIRATE (1926) With a decade of early Hollywood fame and such roles as d'Artagnan, Zorro and Robin Hood behind him, the handsome and athletic film pioneer Fairbanks plays another swashbuckler, helping a man avenge his father's death by infiltrating and overthrowing the group of pirates that captured and destroyed his ship. He saves a Spanish princess in the process in one of the first silent films to be shot in colour.
ERROL FLYNN AS PETER BLOOD - CAPTAIN BLOOD (1935) The dashing and muscular Flynn plays an adventurous and daring doctor-turned-pirate in his debut film that brought him instant stardom. Convicted of treason and sentenced to death, he ends up as a slave, purchased by the elegant Arabella Bishop (Olivia de Havilland). He leads an escape, steals a Spanish ship and goes on to become one of the most feared pirates of the seas, rescuing Arabella from capture.
TYRONE POWER AS JAMIE WARING - THE BLACK SWAN (1942) Another debonair and broad-shouldered Hollywood star, Power as Captain Waring agrees to assist the new Governor of Jamaica in eradicating piracy in the Caribbean. He kidnaps the beautiful Lady Margaret Denby (Maureen O'Hara) and eventually wins her heart. Made in stunning Technicolor, the film was nominated for three Oscars, and won one for Best Cinematography.
GEENA DAVIS AS MORGAN IN CUTTHROAT ISLAND (1995) Directed by Davis's then-husband, Renny Harlin, who was nominated for Worst Director at the Razzies, this film is in the Guinness Book of Records as the biggest box office flop ever (US$11 million return on $100 million production cost). Davis was alluring but wholly unconvincing opposite the ineffectual Matthew Modine as a buccaneer who inherits her father's ship and part of a treasure map.
PENELOPE CRUZ AS ANGELICA IN PIRATES OF THE CARIBBEAN: ON STRANGER TIDES (2011) The sultry Cruz plays the daughter of Blackbeard (Ian McShane) and the love interest of the neurotic you-know-who in this fourth film in the series, about the quest for the Fountain of Youth. Cruz was late in her pregnancy for the shoot and her younger sister Monica was often used as a double.
Compiled by Audrey Coutinho