The Princess Bride and How Image Shaped the Pirate

Piracy has never gone out of style.

Pirates have been a constant throughout world history but the pirates we think of today often take form in how we imagine early modern Atlantic pirates. The late 1600s and early 1700s saw a surge of piracy throughout the Caribbean and into the Americas. Their targets were often British ships and the constant battle against these criminals threatened to destabilise the British American colonies. At least, that’s how British officials viewed the situation.

Our fascination with pirates stems from the colonial era because the colonists often happily worked with pirates. In many cases, the criminals were seen as almost heroic because they smuggled illegal yet desirable goods into the colonies.[1] Colonists wanted more options and pirates provided such goods.

However, in order for pirates to seem a legitimate threat to trade, they had to appear frightening. Newspapers in London and North America printed thousands of reports about pirates’ crimes. In turn, pirates broadcasted their crimes to newspapers that would publish their accounts. They frequently let sailors on captured ships go free so they could warn authorities about the pirates’ horrible crimes.[2]

This historical detail has not gone amiss in 20th and 21st-century popular culture. There have been numerous big screen adaptations of the popular pirate novel, Treasure Island, while, over the past 13 years, Disney has created one of the most lucrative franchises of all time based on its own theme park ride with the Pirates of the Caribbean films.[3]

However, an alternate example shows Hollywood’s success in conveying how pirates had to maintain a specific image in order to succeed. This historical detail shines in the 1987 film The Princess Bride (based off the 1973 novel by William Goldman) with the Dread Pirates Roberts.

In the Princess Bride, the heroine Buttercup has fallen in love with the ‘Farm Boy’, aka Westley, who must leave to make enough money to marry her. Unfortunately, he is soon reported dead at sea at the hand of the infamous Dread Pirate Roberts who leaves no one alive. Later, Buttercup has agreed to marry Prince Humperdink, who in turn has arranged to have her kidnapped and assassinated to start a war with the rival country, Guilder. The kidnappers are soon pursued by a lone ship captained by a ‘Man in Black’, who is no doubt the Dread Pirate Roberts. He is referred to as such because he dresses in all black, including an eye-mask, which adds to the mystery behind his origins and identity.

After besting the three kidnappers in a battle of skills and wits, the Dread Pirate Roberts takes Buttercup for his own. Yet, this is where the twist of the film is revealed. It turns out the Dread Pirate Roberts is actually her true love, Westley.

The twist in Westley’s tale is that one day the Dread Pirate Roberts told him he wished to retire with his riches. Roberts then revealed his secret: ‘I am not the Dread Pirate Roberts. My name is Ryan’. It turns out he had inherited the ship from the previous Dread Pirate Roberts just as Westley was set to do after serving as valet for three years. It turns out the real Dread Pirate Roberts had been retired for over fifteen years and was living like a king in Patagonia. However, the most significant part of this story is this: ‘The name was the important thing to inspire the necessary fear. You see, no one would surrender to the Dread Pirate Westley’.[4]



The Dread Pirate Roberts holds similarities to the real-life infamous pirates Blackbeard and Bartholomew Roberts of the eighteenth century. Both of these pirates depended very much on their reputations for success.

Little is known about the pirate Blackbeard, but thanks to his image he is to this day the most notorious pirate who ever lived. Blackbeard was actually named Edward Teach (sometimes referred to as Thatch) and likely hailed from Bristol. He only served as a pirate captain between 1717 – 1719 until he died in battle off the coast of Charleston, South Carolina. Unlike Bartholomew Roberts, he did not amass much wealth but his notoriety terrified both colonists and British authorities.[5] His most powerful weapon was his image. He grew his hair out long and sometimes attached lit sparklers to his beard to make himself look as frightening as possible. This image was the deliberate antithesis of early modern polite society, with its popular trend of maintaining a clean-shaven face to express cleanliness and civility.[6]



Blackbeard the pirate from A General History of the Lives and Adventures of the Most Famous Highwaymen, Murderers, Street-Robbers, &c., Vol. 1 (London, 1734).


Bartholomew Roberts has the reputation for being the most successful pirate in the history of the Atlantic.[7] Without this pirate, there would be no Dread Pirates Roberts in the Princess Bride. His success, wealth and loyal crew served as the direct inspiration for the fictional pirate of a similar name.[8] He and his crew sailed as far south as Brazil and as north as Newfoundland and gained sinister reputations as pirates. Like Blackbeard, Roberts likely changed his surname for the role and he certainly looked the part. He was described as dressing in crimson coats with feathers in his hat, and wore gold jewellery to signify his wealth.[9] The visible display of wealth indicated his power as a pirate to the public, but in reality he did not embody many piratical characteristics. For instance, he abhorred drinking and maintained a strict order on his ships. He was also surprisingly kind to his victims and, contrary to his cinematic namesake, preferred not to harm anyone if possible.[10] With his strict discipline he intended to create a large and successful fleet of pirates, which he did, and to allow survivors to tell their stories to newspapers.



Similar to the Dread Pirate Roberts, both Blackbeard and Bartholomew Roberts changed their image and their names to create their own personal brands. As Westley said to Buttercup, the name was the most important part of the story. In history, the name of these pirates conjured up frightening images and kept these pirates in our memory to the modern day. Film franchises and movies like The Princess Bride do well to remind us that it is not the actual criminal pirate we admire, but the image they send to the public.

Rebecca Simon recently submitted her PhD thesis to King’s College London. Her thesis examines the public executions of pirates, British legal history and print culture in the early modern Atlantic world. You can find her on Twitter @beckalex. 


[1] Many goods, such as textiles, spices and tea were banned because the British desired a trade monopoly to weaken European competitors in the Americas. Douglas R. Burgess, The Politics of Piracy: Crime and Civil Disobedience in Colonial America (Lebanon, NH, 2014), 27.

[2] Peter T. Leeson, The Invisible Hook: Hidden Economics of Pirates (Princeton, 2009), 117.

[3] The films, I argue, that would not have succeeded were it not for Johnny Depp’s interpretation of Captain Jack Sparrow.

[4] Clip via youtube:

[5] Angus Konstam, Blackbeard: America’s Most Notorious Pirate (Hoboken, 2006), viii, 293.

[6] Alun Withey, ‘Shaving and Masculinity in Eighteenth-Century Britain’, Journal for Eighteenth-Century Studies 36:2 (2013), 229 – 230.

[7] Marcus Rediker, Villains of All Nations: Atlantic Pirates in the Golden Age (Boston, 2004), 33.

[8] Barb Karg and Arjean Spaite, The Everything Pirates Book: A Swashbuckling History of Adventure (Avon, MA, 2007), 228.

[9] Captain Charles Johnson, A General History of the Pyrates (London, 1724), 212.

[10] Ibid, 183.





2 thoughts on “The Princess Bride and How Image Shaped the Pirate

  1. c m maratos says:

    One of my favourite films and very undervalued and overlooked by the public. Great comparisons to actual historical pirates. Great background information regarding the pirates.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s