Arr, mateys! There are few characters that have proven to be both popular and cool as pirates throughout film history. They have graced our screens for as long as cinema has existed, and whether they are portrayed as villains or heroes, they are often characters that exude coolness. Stereotypically, they have a great look with dozens of eccentric accessories, but importantly they sail the seven seas and answer to nobody’s rules but their own (plus the lingo is usually pretty cool too).

In celebration of the 16th anniversary of Pirates of the Caribbean: The Curse of the Black Pearl’s theatrical release, here are 10 of the most notorious swashbuckling pirates from film history.

10. Captain LaRoche (The Pirates of Blood River)

Over the course of his career, Christopher Lee proved himself to be the perfect cinema villain and excelled in roles including Count Dracula, Saruman, Count Dooku, Frankenstein’s Monster and The Mummy. Playing such cool and legendary characters, it is only fitting that he once appeared as a pirate and traversed the seven seas. He got this chance in 1962, with the role of Captain LaRoche in John Gilling’s British action film The Pirates of Blood River. Slightly deviating in this role from his classic English accent and charming persona, he retains a suaveness and is fantastic in the villainous role. Captain LaRoche is menacing and dangerous, but equally cool and intriguing, complete with a French accent. In the film, a group of pirates led by LaRoche attack a 17th Century Huguenot settlement in a quest for treasure and will stop at nothing to obtain it.

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Source: Screenshot via Columbia Pictures

9. Blackbeard (Blackbeard the Pirate)

A notorious real-life English pirate who operated around the West Indies, Blackbeard appears in many works of fiction. One of the most notable is Blackbeard the Pirate, which was directed by Raoul Walsh and released in 1952. The plot sees Robert Maynard, a British Navy Lieutenant, who attempts to prove that privateer Henry Morgan (Torin Thatcher) engages in piracy. Maynard finds himself working aboard a ship captained by Blackbeard (Robert Newton), who just happens to be engaged in conflict with Morgan. Newton does a terrific job playing the fearsome pirate, complete with a fine beard, and although the film may seem a little dated by today’s standards, there is no doubt that this movie and the characterization helped to define the typical Hollywood pirate as we know it today. It is a fun and exciting flick, and also one of the most important pirate films in cinema history.

http://www.slothmorse.com/2014/09/19/talk-like-pirate-day/ Source: Slothmorse.com
Source: Screenshot via RKO

8. The Black Pirate (The Black Pirate)

One of the earliest screen portrayals of a pirate, the 1926 silent adventure film The Black Pirate was shot entirely in two-color Technicolor and was just the third feature to be filmed this way. This makes it an important film, which is furthered by legendary action hero Douglas Fairbanks’s fantastic portrayal as the titular character. Fairbanks masterfully portrays the character in the silent medium through his physical actions and facial expressions, however, he manages to do this without it being over the top and without too much pageantry (this is also aided by the advancement in Technicolor). There are many great swordfights and stunts, but the film and character of The Black Pirate is perhaps best remembered for the famous sequence where he slides down the sails. This action is now a must for any pirate and is regarded as Fairbanks’s finest moment.

https://quixotando.wordpress.com/2009/09/19/international-talk-like-a-pirate-day/ Source: Quixotando.wordpress.com
Source: Screenshot via United Artists

7. Wesley/Dread Pirate Roberts (The Princess Bride)

This 1987 fantasy comedy adventure film is considered an ’80s classic and this is largely thanks to the character of Westley/Dread Pirate Roberts (Cary Elwes). Westley becomes a pirate to save his childhood sweetheart, Princess Buttercup (Robin Wright), from kidnappers and the evil prince she is set to marry. In addition to a cool all-black costume, Dread Pirate Roberts has all the traditional characteristics of a fairytale pirate (although he spends little time at sea) and has many great action sequences, but a part of this film’s charm is also the subtle comedy that goes along with it and being able to balance both action and romance to perfection. It is a fun, quotable and dramatic family film which became a cult classic and what is considered one of the most re-watchable films of all time. Elwes perfectly portrays the character of a hero pirate, which is somewhat of a rarity.

http://www.bloomberg.com/bw/articles/2013-10-03/silk-roads-dread-pirate-roberts-versus-the-princess-brides Source: Bloomberg.com
Source: Screenshot via 20th Century Fox

6. Captain Barbossa (The Pirates of the Caribbean)

Although he is not the coolest pirate in the film series, there is no doubt that Captain Barbossa from The Pirates of the Caribbean is one of the greatest movie pirates to grace the big screen. Masterfully portrayed by Geoffrey Rush, Barbossa is introduced as the villainous and undead captain of the Black Pearl after committing mutiny against Jack Sparrow and is a key character throughout the saga. In addition to looking the part of a dirty and weathered pirate with all the necessary accessories, he also has the perfect voice and treacherous and untrustworthy personality of a classic pirate who goes by his own code. Although not all of the films are fantastic, they are largely aided by Captain Barbossa and his complex relationship and history with Jack Sparrow. Captain Barbossa also gets bonus points for being resurrected and his brilliant re-introduction at the climax of Dead Man’s Chest.

http://pirates.wikia.com/wiki/File:Hector_Barbossa_-_On_Stranger_Tides.JPG Source: Pirates.wikia.com
Source: Screenshot via Walt Disney Pictures

5. Captain Jamie Waring (The Black Swan)

Both a love story and an action packed swashbuckling adventure, Henry King’s 1942 film is based on the novel by Rafael Sabatini and features a fictionalized version of notorious buccaneer Henry Morgan. The star, however, is Captain Jamie Waring (Tyrone Power), who is charming, stylish and a man of action. After peace is made between England and Spain, former pirate Henry Morgan is made Governor of Jamaica and tasked with stopping his old comrades. To do so, he enlists his young pirate friend Captain Jamie Waring and his lieutenant, Tom Blue (Thomas Mitchell). Not trusted by either the residents or the pirates, Waring falls for the former Governor’s daughter, Lady Margaret (Maureen O’Hara), and it is up to him to save the day and get the girl. Although a heroic character, he also retains a rogue and dangerous persona which has since become very popular in pirate, and other, movies.

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4. Captain Blood (Captain Blood)

In addition to the great name, Captain Blood (Errol Flynn) is also one of the greatest film pirates of all time. A likable hero with bags of charisma and athletic prowess, he is a former physician turned pirate to get revenge on the system which falsely accused him of treason. This sees him go on a swashbuckling adventure which allows him to be the hero whilst acting like a pirate, and it was such a memorable first major performance from Flynn that it helped to launch his career. He went on to become one of the greatest action heroes in the 1930s, including playing Robin Hood in the 1938 classic, The Adventures of Robin Hood (also directed by Michael Curtiz). Captain Blood was also the first of eight films co-starring Flynn and Olivia de Havilland, making them an important duo in swashbuckler films which were hugely popular at the time.

http://www.doctormacro.com/movie%20star%20pages/Flynn,%20Errol-Annex.htm Source: Doctormacro.com
Source: Screenshot via Warner Bros.

3. Long John Silver (Treasure Island)

One of the most famous fictional characters of all time and the source of inspiration for the majority on this list, Long John Silver is a Robert Louis Stevenson creation and the main villain in the classic 1883 novel, Treasure Island. He has since appeared in dozens of other stories and is considered to be the quintessential pirate (complete with a parrot on his shoulder and a missing leg). There are numerous portrayals which could be included (Muppets Treasure Island getting an honorable mention), but it is the 1950 adaptation of Treasure Island that gets the nod. Long John Silver is brilliantly played by Robert Newton, who captures the pure evil and manic persona whilst retaining the all-important coolness that the character requires. It was such an excellent portrayal, that it set the standard for screen portrayals and he even reprised the role a few times (and later played Blackbeard).

http://www.theguardian.com/culture/2014/nov/28/the-10-best-pirates Source: Theguardian.com
Source: Screenshot via Walt Disney

2. Captain Hook (Peter Pan)

Another classic literary character is Captain Hook, who is created as the villain in J.M Barrie’s famous novel and play, Peter Pan. There have been numerous brilliant portrayals of the instantly recognizable character, including Dustin Hoffman’s in the 1991 film Hook, but the greatest is the 1953 Walt Disney Animated Classic. Captain Hook, voiced by Hans Conried, is seeking revenge on Peter Pan who cut off his hand and fed it to a crocodile. He is very dangerous and evil, but also very stylish. For comic effect, he is also portrayed as a cowardly character with a childish temper and is completely reliant on his assistant, Mr. Smee. Although his cowardice is atypical of many other pirates, there is no doubt that he is a classic villain with a fantastic physical appearance which will instantly spring to mind whenever discussing fictional pirates.

http://disney.wikia.com/wiki/Captain_Hook Source: Disney.wikia.com
Source: Screenshot via Walt Disney

1. Captain Jack Sparrow (Pirates of the Caribbean)

There has been a rejuvenated interest in pirates in the last 15 years, and this is all thanks to The Pirates of the Caribbean and Johnny Depp’s brilliant portrayal of Captain Jack Sparrow. An antihero with loose morals and a cowardly personality who appears only out for himself, he remains very likable due to his comedic actions, cool appearance, a penchant for danger, and even heroic deeds, when push comes to shove. Depp based his characterization on Keith Richards and Pepe Le Pew, which proved to be the perfect combination as he has emerged as one of the most popular film characters of recent times. His ambiguous motives make him an intriguing character and one of the great modern antiheroes, but he is also an excellent swashbuckling combination of comedy, drama, action, and romance which has helped him win audiences over ever since appearing on our screens for the first time in 2003.

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Source: Screenshot via Walt Disney Pictures