Cindy Vallar, Editor & Reviewer
P. O. Box 425, Keller, TX  76244-0425

Real-world pirates were criminals. They were dark rulers of the high seas. They plundered, pillaged, smuggled, and killed anyone who got in their way. Hollywood pirates, though, are more of the “tall, dark, and handsome” sort. They may plunder and smuggle, but only to get the girl and smite those girls’ greedy suitors.

 
So the Treasure Was Divided by Howard Pyle

Captain Jack Sparrow explained his misdeeds in 2003’s Pirates of the Caribbean: The Curse of the Black Pearl as follows: “Me? I’m dishonest, and a dishonest man you can always trust to be dishonest. Honestly. It’s the honest ones you want to watch out for . . . .” The statement seems to describe many fictional pirates – they are dependably unpredictable.

 

As an employee of a costume shop that specializes in pirate garb, I’ve encountered my fair share of pirate films. Here’s a list of my favorites. They all feature pirates who are technically criminals. They do bad things, but I can’t help but love them.

The List

Pirates of Penzance, 1983

In the movie Pirates of Penzance, the main character Frederick (Rex Smith) signs up to apprentice as a pilot, but ends up apprenticing as a pirate due to a miscommunication. Frederick is placed with the Pirate King (Kevin Kline), leader of the Pirates of Penzance. Frederick does not want to be a criminal, so he makes a personal commitment to ridding the seas of pirate ruffians. The movie is a musical comedy, so the presence of pirates who can sing and dance makes it hard not to love the musical mateys.

The Goonies, 1985

“Goonies” is the nickname for a group of outcast preteens, who are the underdog protagonists of the film. The movie is set in the 1980s, when the Goonies discover an old treasure map that supposedly leads to the famous (at least in hometown lore) pirate One-Eyed Willie's buried treasure. We don't ever meet Willy, but the fact that his legend inspired this quirky quest and childhood classic secures its place in my heart and on this list.  View the trailer

Treasure Island, 1934

This movie is based on Robert Louis Stevenson’s classic novel and involves a journey to find, you guessed it, a treasure island. Very loosely, the adventure begins with rumors of treasure and young Jim Hawkins’s (Jackie Cooper) discovery of a map. When Jim embarks on his journey, he is warned about a one-legged pirate named Long John Silver (Wallace Beery), whom he quickly encounters. Throughout the film, Long John Silver has lovable moments, leaving Jim confused as to whether or not Silver should be trusted. How does it turn out in the end? You’ll have to watch to find out.  Learn about the novel

Pirates of the Caribbean: The Curse of the Black Pearl, 2003

Pirates of the Caribbean is a Disney film franchise that was created because the pirate ride at Disney World had decreased in popularity. Rather than let the ride sit unused or tear it down, the company decided to create a movie in hopes of making the public fall in love with pirates. They succeeded. In 2003 Disney brought us Captain Jack Sparrow (Johnny Depp). Sparrow is the ultimate lovable bad boy: he’s good-looking; he can swing a sword; he has a great sense of humor; and he takes away riches from greedy overlords. Disney makes the audience fall in love with him, and then they take him away, leaving everyone wanting more. View the trailer

[This pirate movie likely has the highest budget of any of the movies on the list. The other movies in the franchise, released after The Curse of the Black Pearl, follow a similar pattern to this one, so I only included one on the list.]

 

Peter Pan, 1953

This animated classic is based on J.M. Barrie’s play, Peter Pan, or the Boy Who Wouldn’t Grow Up. After pre-teen Wendy is told it is time for her to grow up, she is visited by Peter Pan, who promises her a life of never having to. He takes her and her younger brothers, John and Michael, to the magical Never Land. Never Land is full of happiness and fun until Peter’s nemesis, the pirate Captain Hook, captures Wendy, her brothers, and Peter’s friends, the Lost Boys. Peter must outwit Captain Hook to save them. Although the pirates in this movie are mean, they are also dim-witted and often humorous, which make themhard to dislike.

Hook, 1991

Hook delves into what happens when Peter Pan grows up. Now a stodgy businessman with children of his own, he has forgotten the things that were so important to him as a child: adventure, friendship, and fun. When Captain Hook kidnaps his children, Peter must return to Never Land and face his arch-nemesis, and team up with a number of old favorites, like Tinkerbell and the Lost Boys.)  Dustin Hoffman plays Captain Hook, and Bob Haskins is his pirate sidekick, Smee, so of course, the pirate characters are irresistibly fun.

Captain Blood, 1935

Captain Blood opens when Dr. Peter Blood (Errol Flynn) is falsely convicted of treason and sold into slavery. In an effort to become free again, the doctor and his enslaved friends rebel and take over the Spanish ship that attacked the city of Port Royal. The rebels flee and become some of the most feared pirates of the seas, but when they return to Port Royal, they find it has been taken over by France. There, the rebels must determine whether they should join the new king or maintain their feared status. The moral struggle they face is the perfect example of unpredictable, lovable pirates. They broke out of jail, but they were wrongly imprisoned. They fought against Port Royal, but now should they fight for it? Watch to see.  Learn about the author of Captain Blood     Learn about the history behind the novel

The Princess Bride, 1987

The Princess Bride is a movie with a unique cast of characters: a giant, a royal family, the Dread Pirate Roberts, a six-fingered man, an albino, a town booer, and even a medicine man. The plot is unique, too. There is a standard romantic love triangle, but also an attempt at memory erasing, a royal wedding, a fire swamp filled with terrible obstacles – quicksand and rodents of unusual size – the avenging of a loved one’s death, and, of course, sword play. As you can see, the description for this pirate flick is a bit complex, so I’ll leave it at “nothing is as it seems, but everything is as you wish.”