What Are the Best Pirate Movies of All Time?

Yo-Ho, Yo-Ho, A Pirates Film For Me

Hollywood has always loved a good pirate tale starting matinee idols like Douglas Fairbanks in the old silent days and on up through the phenomenal success of Johnny Depp as Captain Jack Sparrow. If you want to find adventure on the high seas, here are the best cinematic buccaneers to set sail with, plus a few female pirates to cross sword with.

1
Captain Blood (1935)

© Warner Home Video

Errol Flynn epitomizes the roguish, swashbuckling captain as a good doctor who becomes a pirate to get revenge on the officials that wrongly accuse him of treason in this stellar adaptation of Rafael Sabatini's novel. Another of his novels was the basis for the 1940 The Sea Hawk.

With his dashing good looks and devilish grin, Flynn is born to play these Sabatini heroes. He had just the right blend of sincerity, brash charm, and humor. Here he is paired with the lovely Olivia de Havilland. Basil Rathbone plays his arch nemesis. Just when Rathbone is about to whip him within an inch of his life, the town is attacked, and Flynn exclaims with a grin, "What a timely interruption!" Absolutely delightful. Buy from Amazon »

2
The Crimson Pirate (1952)

The Crimson Pirate
Warner Bros.

Set in the Caribbean of the late 1700s, this jocular, robust, and colorful adventure involved tons of swordplay, a prison break, a revolution, and an eccentric scientist. As a young man Burt Lancaster had joined the circus as an acrobat. As the titular Crimson Pirate, he gets to put those skills to excellent use and to partner with his circus buddy Nick Cravat. Lancaster and Cravat fly around the sets with amazing acrobatic skill, and Lancaster flashes some pearly whites that are downright blinding. Buy from Amazon »

3
Princess Bride (1987)

The Princess Bride
20th Century Fox

Cary Elwes is a young farm boy who takes on the persona of Dread Pirate Roberts in order to save his beloved. Rob Reiner's film manages to be utterly sincere at the same time that it sends up every fairy tale cliché with enchanting wit.

The costume for Dread Pirate Roberts was modeled on what Douglas Fairbanks wore in The Mark of Zorro. Though he isn't a pirate, Mandy Patinkin plays the dashing and revenge driven Inigo Montoya, which only adds to the film's wonderful sense of swashbuckling fun.

4
A High Wind in Jamaica (1965)

A High Wind in Jamaica
20th Century Fox

Most Hollywood pirate films are about adventure and a fantasy image of what pirates are like. A High Wind in Jamaica tries to temper that fantasy with a little sense of what real pirate life might have been like.

The film is essentially told from the point of view of two English children who end up on a pirate ship. The children are thrilled, and the young girl even develops a friendship of sorts with the pirate captain. But the crew want to rid themselves of the troublesome youngsters and the story eventually takes a tragic turn. Anthony Quinn and James Coburn are the sympathetic pirates. Buy from Amazon »

5
Pirates of Penzance (1983)

The Pirates of Penzance
Universal Pictures

This film adaptation of Joseph Papp's production of the Gilbert and Sullivan operetta is highly uneven, but it does boast one of the best screen pirates in Kevin Kline's Pirate King. Kline's performance is so larger than life that it practically leaps off the screen. Kline displays an old school matinee idol charisma that proves far more memorable than the film. Buy from Amazon »

6
Pirates of the Caribbean (2003)

Pirates of the Caribbean
Pirates of the Caribbean. © Walt Disney Pictures

Johnny Depp plays Captain Jack Sparrow in this adaptation of the Disneyland theme park ride. He captivated audiences and continues to play the character in multiple blockbuster sequels.

His take on the conniving captain is to play him like a rock star and to walk as if he were constantly trying to compensate for a swaying deck -- even when he's on dry land. Depp revealed that he looked at the Rolling Stones' Keith Richards for inspiration, and in later films Richards made cameo appearances as Sparrow's wayward dad.

7
The Black Pirate (1926)

The Black Pirate
United Artists

No pirate list can be complete without at least one Douglas Fairbanks film. Here he plays a nobleman who becomes a pirate to avenge his father's death. The ever-exuberant and athletic Fairbanks is great fun to watch and the film boasts an early Technicolor process, making it one of the first color feature films. Buy from Amazon »

8
The Black Swan (1942)

The Black Swan
20th Century Fox

Tyrone Power was a handsome leading man of the 1940s, and here he stars in a vibrant Technicolor pirate adventure. The story involves a reformed pirate captain who enlists former buccaneers to help him rid the seas of pirates. Power is one of the reformed pirates, and George Sanders and Anthony Quinn are two of the troublemakers. Maureen O'Hara is the love interest. A rollicking good time for all. Buy from Amazon »

9
The Pirates of Blood River (1961)

The Pirates of Blood River
Columbia Pictures

The only good thing on display here is the sense of menace Christopher Lee brings to his role as the ruthless pirate Captain LaRoche. The violence in this Hammer production was repeatedly cut back in order to get a more kid-friendly rating, so both piranhas and the word "harlot" were excised from prints. Oliver Reed also appears as one of the pirates. Lee would play another Hammer Films pirate in The Devil-Ship Pirates. Buy from Amazon »

10
Peter Pan (1953)

Peter Pan
Walt Disney Pictures

Also from Disney comes another iconic pirate: Captain Hook. This animated tale featured is based on James M. Barrie's famous children's book. Hans Conried voices the evil Captain Hook, and he made an impression on many generations of children.

Honorable Mentions:

Against All Flags (1952)
I need to extend the list by two to include a pair of female pirates. Here, Errol Flynn plays an English officer who goes undercover to infiltrate a pirate stronghold. There he meets the fiery Maureen O'Hara and even has the opportunity to cross swords with her. O'Hara makes a fine female pirate and handles the swordplay quite well. She also strikes some sparks onscreen with co-star Anthony Quinn.

Anne of the Indies (1951)
Jean Peters' is Captain Anne Providence, one of the most notorious pirate leaders of the Spanish Main. She must fend off rivals like Thomas Gomez's Blackbeard as well as the amorous advances of Louis Jordan's suave French captain Pierre la Rochelle. She delivers a feisty performance as one of the screen's most memorable lady pirates.

Edited by Christopher McKittrick Buy from Amazon »