A pirate flag flies against a dark and stormy sky

At Booty Bingo, we not only love playing bingo — we also adore all things pirate… arrrrggh! That’s why we’ve put together a list of the greatest pirates from fiction. Keep reading to find out who we think are some of the most celebrated fictional swashbuckling scallywags of all time!

Dread Pirate Roberts – The Princess Bride

Dread Pirate Roberts isn’t one person, but rather a title that many different people use in both the novel and film versions of The Princess Bride. Dread Pirate Roberts is a pirate with a fearful reputation, known for his skills with a sword and his sheer brutality, showing no mercy to those he comes across.

However, we discover as the story unravels, this is not necessarily the case. Over time, many people have assumed the name of “Dread Pirate Roberts” for their own purposes and, depending on who you came across and what their motives were, you might have been spared.

In The Princess Bride, our hero Westley finds himself at the mercy of the infamous pirate, who initially spares his life but warns him he may take it whenever he feels like it. Over time, the two become friends and the current Dread Pirate Roberts reveals his true identity, as well as the fact that he’s used his predecessors’ reputation to plunder and steal, all without having to slay a single person. When his targets discover that he is the legendary pirate, they simply hand over their cargo and riches, rather than facing his wrath.

In a cheeky ploy, Westley later adopts the name himself to achieve his goals.

Long John Silver – Treasure Island

A stash of pirate treasure hidden in a cave

Long John Silver is the ruthless pirate from the classic novel, Treasure Island (amazingly first published in 1883). In the book, Silver represents all that we know a pirate to be today: he has a parrot, one leg, and uses his charm to his own benefit.

Despite his soft spot for the hero of the story, Jim Hawkins, Long John Silver is undoubtedly a true pirate by nature. During the story, we discover Silver was the leader of the mutiny and the cause of all the trouble for the loyal members of the ship’s crew. Despite this, when Jim faces certain death later in the story, Silver saves him, even though he keeps him as a hostage.

Later in the tale, Silver steals some of the treasure and escapes alone, showing that despite his clear affection and fatherly mentorship of Jim, he is a pirate through and through.

Monkey D. Luffy – One Piece

This is a character that some players may not be familiar with, but bingo fans who also enjoy Japanese comic books and animation will be familiar with Monkey D. Luffy, the Captain of the Straw Hat Pirates, and the protagonist of the mega-hit Japanese comic One Piece. This comic, or manga, has sold more than 470 million copies across the world, spawned a popular TV show, movies, hundreds of different types of fan merchandise, and–even though it recently closed–a mini theme park.

In One Piece, we follow Luffy as he and his pirate crew travel around the world in search of the legendary pirate treasure, “One Piece”, which will allow Luffy to become the legendary Pirate King. Along the way, they face lethal foes, lose some friends, and gain some new ones, as they grow into a powerful pirate crew!

LeChuck – Monkey Island

A young woman plays games on a computer.

Older fans of video games may remember the good, old days of point-and-click video-game adventures, where the player guided a character around the screen, picking up items, interacting with characters and solving puzzles. One of the most legendary point-and-click series of games was (and is) called Monkey Island, which featured the legendary villain, the (mostly) undead pirate captain LeChuck!

LeChuck yearns for the heart of Elaine Marley, the heroine and love interest in the series, but often finds his dastardly plots ruined by Guybrush Threepwood, the hero of the franchise. LeChuck also has an insatiable desire for power, but despite often wielding mysterious voodoo powers, his arrogance and gullibility often leads to his defeat at the hands of Guybrush.

The Pirate Captain – The Pirates! Band of Misfits

Most of us will recognise the Pirate Captain from the 2012 3D and stop-motion animated film The Pirates! Band of Misfits, or as it is better known in the UK, The Pirates! In an Adventure with Scientists!

This film was produced by Aardman Animations, whose genius team also created other claymation films such as Wallace and Gromit, and Sony Pictures Animation. But this was not the first time the world got to experience the silly antics of The Pirate Captain, who first came to life in The Pirates! series of comedy novels.

The Pirate Captain may look like a typical pirate, but he’s unfortunately not very good at it. Thankfully his good nature, pleasant face, and love of ham has won the loyalty of the pirates in his crew.

Captain Jack Sparrow – Pirates of the Caribbean

Illustration of a pirate on a beach watching a ship in the bay during a full moon.

Would any of us have remembered Pirates of the Caribbean if it hadn’t featured Johnny Depp’s legendary portrayal of witty scallywag, Captain Jack Sparrow? Probably not. Unlike many of the other pirates in the series of hit films, Sparrow is obviously not an evil pirate, but neither is he a particularly good one. His character is very charming, self-serving, and has the wit and cunning to get himself into and out of some dire situations.

Throughout most of the films, Sparrow struggles between good and evil, but ultimately he always returns to help his friends, even if it’s against his best interests. Although in a strange way, Captain Jack Sparrow always gets what he wants in the end.

Honorary mention – “Captain” Abduwali Muse – Captain Phillips

Even if you haven’t seen the great film Captain Phillips, you’ll have likely seen the fantastic meme “I’m the Captain now”. This is why “Captain” Muse, even if he’s not the type of pirate we’re usually referring to here at Booty Bingo, makes it onto our list. And yes, Captain Phillips is based on a true story, but we know Hollywood often pushes the boundaries of what this means, which is why we’re referring to him as a fictional character.

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