The 10 Best Pirate Films of All Time

Pirates continue to capture the public imagination, particularly with the revival of the swashbuckler over the past decade with Disney's Pirates of the Caribbean franchise. And no great wonder - pirates, both as cultural and historical figures, are absolutely fascinating. Historically, pirates often thrived in a truly democratic society, with all plunder divided equally, compensation for limbs lost, and captains elected by vote (and also removed by vote), in marked contrast to the near slavery and abhorrent conditions under which, for example, the crews of the English Navy lived. (For a fascinating read about historical pirates that gives a strong overview as well as biographies of the most notorious pirate leaders, I recommend Nigel Cawthorne's A History of Pirates: Blood and Thunder on the High Seas.) In the cultural imagination, fostered by Stevenson's Treasure Island and N. C. Wyeth's original illustrations, pirates are vivid, ribald, charismatic characters and it's no wonder that their adventurous lives have been the inspiration for many great films. Here are the ten greatest pirate films:

10. Peter Pan (1960)
Captain Hook is one of the most enduringly great pirate characters of fiction and one need look no further for a definitive interpretation of the crocodile-phobic pirate than Cyril Ritchard's delightfully witty performance. This version of Peter Pan (starring the marvelous Mary Martin in the title role) can be difficult to track down; it was originally produced as a live, color television broadcast and has happily been preserved. With splendidly clever songs by Mark "Moose" Charlap, Jule Styne, and Carolyn Leigh (with additional lyrics from Betty Comden and Adolph Green), including my favorite "Oh My Mysterious Lady," this version is essentially a filmed stage play, but oh what a wonderful one it is! Though the 1953 Disney version is probably the best known, nothing can top this marvelous telling of the classic J. M. Barrie story.

9. The Crimson Pirate (1952)
Burt Lancaster stars as Captain Vallo, a devious pirate captain who, along with his faithful sidekick Ojo (Nick Cravat), forms an alliance with a rebellion against the evil Baron Gruda (Leslie Bradley). As thoroughly tongue in cheek as a film could be, The Crimson Pirate allows Lancaster and Cravat - Lancaster's long-time physical trainer - the chance to demonstrate their extraordinary athleticism, with many of the acrobatic stunts verging on the balletic. Originally written as a suspenseful serious drama, the first draft was thrown out because of the screenwriter Waldo Salt's communist affiliation; the final draft is the complete opposite, a feisty, wildly entertaining romp through pirate legends and a pure delight for any pirate film aficionado.

8. The Princess Bride (1987)
William Goldman provided the adaptation of his own brilliant satiric novel for this cult favorite directed by Rob Reiner. Cary Elwes stars as Westley, a farm boy, whose true love Buttercup, played by Robin Wright, is devastated when she hears the news of his supposed death at the hands of the Dread Pirate Roberts. Years pass and Buttercup is chosen as the bride for the eely Prince Humperdinck (Chris Sarandon), who is accompanied at all times by the six-fingered Count Rugen (Christopher Guest). Conspiracy, death-defying adventure, nail-biting escapes, and most of all true love - these are the stuff from which this superb fantasy is woven. The film is also supremely funny, with terrific performances by Mandy Patinkin, as a revenge-obsessed Spaniard, Billy Crystal, as Miracle Max, Wallace Shawn, as the Sicilian self-described mastermind who finds everything inconceivable, and Andre the Giant, as the good-hearted and immense Fezzick.

7. The Sea Hawk (1940) 
Consummate swashbuckler Errol Flynn was never better in his star turn as English privateer Geoffrey Thorpe in the very best version of the oft-adapted novel by Rafael Sabatini. Thorpe is one of a group of English sailors who call themselves the Sea Hawks and plunder the ships of the Spanish monarchy to fill the coffers of the English queen, but his blithe pillaging is complicated when he ransacks the ship of the Spanish ambassador (the impeccable Claude Rains) and his lovely niece (Brenda Marshall). Special mention should be made of Erich Wolfgang Korngold's stunning, vivacious score, one of his best, and also of Flora Robson's performance as Elizabeth I. More famous names like Bette Davis and Cate Blanchett may come to mind when we think of the great English monarch, but Robson is downright thrilling, particularly in her final speech.

6. The Pirate (1948)
One certainly doesn't immediately associate Vincente Minnelli, Judy Garland, or Gene Kelly with swashbucklers, but they are the director and stars of this great unrecognized pirate film. Manuela (Garland) is a sheltered girl living in the Caribbean, her imagination inflamed by tales of the notorious pirate Macoco. Serafin (Kelly) is a womanizing traveling player who impersonates the infamous pirate, but finds that he gets a good deal more than he bargained for, as Manuela is no wilting wallflower. Manuela's intensely sexualized imagining of the pirate is sublimated in one of Judy Garland's best songs, "Mack the Black," and one of the most explosive dance sequences Kelly ever choreographed. Though more a fantasy musical than a traditional swashbuckler, The Pirate is a very under-appreciated masterpiece. This film also offers a rare opportunity to see the extraordinary Nicholas Brothers in Technicolor.

5. Pirates of the Caribbean (2003, 2006, 2007, 2011) 
Though the latest entry in Disney's wildly successful franchise is decidedly weaker than the first three, the Pirates of the Caribbean films are a magnificent addition to the swashbuckler genre. This is first and foremost because the screenplays by Terry Rossio and Ted Elliot are consistently and brilliantly witty, with an unusually well-structured plot given the complexity of the films, many homages to earlier pirate films, and a slew of running gags. The films are also among a very small number of contemporary films that employ a large cast of character actors, many almost as popular as the leads. The lead actors are also excellent, with Johnny Depp in his career-defining role of Captain Jack Sparrow and Geoffrey Rush as the ultimate blood-thirsty buccaneer. One wishes that other current franchises were as well-crafted and smart.

4. The Black Pirate (1926) 
One of the earliest pirate films, The Black Pirate defined many of the key elements of the genre. Starring the dazzlingly athletic Douglas Fairbanks, the film is about a swordsman who calls himself the Black Pirate, set on avenging his father's death, and who is given the chance to secure power and save his own life if he successfully captures a wealthy merchant ship single-handedly and ransoms the noble lady aboard her. One of the earliest experiments in color filmmaking, this silent film dazzles with its spectacular stunts (many of which would terrify even the most hardened contemporary stuntman and probably wouldn't be attempted today), its outstanding fencing choreography, and Fairbanks's charismatic performance, one of his best. 

3. Mutiny on the Bounty (1935)
Widely considered the best adaptation of Charles Nordhoff and James Norman Hall's novel based on an actual mutiny that occurred in 1789, this suspenseful drama stars Charles Laughton in one of his best roles as the reprehensible, iron-fisted Captain Bligh and Clark Gable (rather disturbingly sans moustache) as Fletcher Christian, first mate, defender of the crew, and eventual leader of the mutiny. The film examines the miserable conditions aboard navy ships quite realistically and the screenplay by Talbot Jennings, Jules Furthman, and Carey Wilson thrillingly depicts the complexities of life on a ship run by a tyrant. The film would go on to win the Oscar for Best Picture and garner nominations for Best Director, Best Actor (Laughton, Gable, and Franchot Tone all received nominations), Best Writing, Best Music, and Best Film Editing.

2. Treasure Island (1950) 
Stevenson's novel is the essential pirate novel and it is the source for dozens of now-common ideas about pirates, like the black spot, treasure maps marked with an X, and parrots as pets. This is my personal favorite version, both a strikingly well-written adaptation (the screenplay is by Lawrence Edward Watkin) and the first appearance of Robert Newton in what would become his signature role of Long John Silver. Newton invented pirate-speak for his performance and is still being imitated today; he would play the role again in two unauthorized sequels, Long John Silver and The Adventures of Long John Silver. He is joined by Bobby Driscoll (the voice of Peter Pan) as young master Hawkins and Finlay Currie as Billy Bones.

1. Captain Blood (1935) 
Captain Blood is perhaps the greatest swashbuckler of all time and stars Errol Flynn, the ultimate swasher and buckler, in his first major role, opposite Basil Rathbone, who gives another brilliant performance as a menacing villain, and Olivia de Havilland, the first lady of swashbucklers. The story follows a doctor whose good intentions lead him to an accusation of complicity of the Monmouth Rebellion. Sentenced to transportation and enslavement, he escapes and reinvents himself as Captain Blood, the honorable pirate, welcoming escaped slaves to his crew and preying on merchant ships in the Caribbean. Directed by Michael Curtiz (The Adventures of Robin Hood, The Sea Hawk) and with an exceptionally good score by the great composer Erich Wolfgang Korngold, Captain Blood is the greatest pirate film of all time.

Honorable mentions: Captain Kidd (1945) starring the incomparable Charles Laughton at his most sneering; Blackbeard's Ghost (1968) starring the freakishly brilliant Peter Ustinov in unfortunately less than brilliant surroundings; Master and Commander: The Far Side of the World (2003) directed by Australian Peter Weir and starring Russell Crowe in one of his best roles; Stardust (2007), which features Robert De Niro in an extended cameo as a gay pirate captain enamored of his reputation as a bloodthirsty killer; The Swiss Family Robinson (1960), one of the finest of the Disney Studio's live action films.