The 8 Best Pirates of All Time, Ranked (One Piece, Games, Movies, & More)

Treasure Island, Pirates of the Caribbean, and One Piece have shaped the modern image of pirates. Be it the confident swashbuckling hero, the carefree spirit driven by a thirst for adventure, the bumbling idiot, or the cutthroat killer, fictional pirates come in a few styles, but nearly all of them have something in common: they are consistently and reliably cool. Games like Assassin's Creed 4: Black Flag let players step into a long-gone part of history where the high seas represent total freedom, a type of romanticization that taps into people's desire to break free from the shackles of government and society.

When somebody in 2026 thinks of a "pirate," they are far more likely to picture Kermit the Frog in a captain's hat than historical figures like Anne Bonny or Black Bart. That is wild to think about, but the idea of a pirate is far more alluring than real piracy. Let's take a trip through fictional history to highlight the very best pirates from literature, movies, games, and, naturally, anime.

We are going to stick solely to traditional sea pirates; no sky or space pirates. The latter are way too hard to properly classify, and it would be weird to place somebody like Metroid​​​​​'s Ridley among these upcoming characters.

One exception aside, we are sticking to one character per franchise. Otherwise, this would be mostly One Piece characters.

8 Captain Flint (James McGraw)

The Original Pirate Ghost Story & The Ultimate Legend

• Debut: Treasure Island (1883) by Robert Louis Stevenson
• Most Relevant Appearance: Black Sails (2014-2017)
• Captain of the Walrus

Let's get the exception out of the way early. In Treasure Island, Captain Flint hangs over the story like a specter, his hidden treasure driving the rest of the characters to hell and back. Important as he is to the narrative, Flint is primarily a ghost story and myth rather than an actual character; however, Black Sails rectifies that by focusing entirely on the mysterious captain.

Everyone is a monster to someone. Since the world has given me the label, I shall choose to live by it. — Captain Flint in Black Sails

The prequel series shows Flint (or James McGraw, as he is first known) to be dark, dangerous, and calculating. Rather than craving gold, women, or entertainment, Flint seeks to start a war, a goal driven by his history with the government. Formerly a celebrated officer, he was vilified and depicted as a monster; consequently, he decided to become the worst version of the villain he is portrayed as. He is a tragic figure who is willing to go against the whole world, and he shows how far a person is willing to go while driven by a grudge.

7 Edward Kenway

A Pretty Realistic Example Of A Fictional Pirate

• Debut: Assassin's Creed 4: Black Flag
• Captain of the Jackdaw

The idea that pirates were driven by a "call to adventure" or a "love for the sea" is a beautiful romanticism, but it's one born of fiction, not history. Silly as Assassin's Creed can get at times, Ubisoft's games strive to be somewhat historically accurate, and Black Flag's handling of Edward Kenway serves as a prime example. Born into a struggling family, Edward's turn to piracy is driven by desperation and, also, arrogance. Not only isn't he a hero, but he doesn't even become a pirate willingly, as the 1713 Treaty of Utrecht turned him into one.

For years, I've been rushing around, taking whatever I fancied, not giving a tinker's curse for those I hurt. Yet here I am, with riches and reputation, feeling no wiser than when I left home. Yet when I turn around and look at the course I've run, there's not a man or woman that I love left standing beside me. — Kenway in Black Flag

Black Flag lets players embody every part of the pirate life, be it ship-to-ship combat, diving for treasure, hunting, or politics. While not straight-up depicted as a villain, the game paints Edward in a morally grey light that likely comes close to reflecting the life that real pirates experienced. He starts as a scoundrel seeking to prove his worth, chasing glory and a twisted sense of freedom at the expense of the people who actually matter to him.

Kenway is also the only captain to have a stealth ship. That must count for something.

6 Dread Pirate Roberts (Aka, Westley)

Reputation Maketh The Pirate (And, Also, The Dreamiest Of Pirates)

• Debut: The Princess Bride (1973) by William Goldman
• Most Famous Version: Cary Elwes's portrayal in The Princess Bride (1987)
• Dread Pirate Roberts is a title, not a single person.

Ah, now for something a touch more lighthearted and way more romantic. Along with being hilarious, The Princess Bride is a throwback to old-fashioned swashbuckling stories popularized by the likes of Errol Flynn; in fact, Cary Elwes's Westley is basically just an Errol Flynn character with the humor turned up to 11. Dread Pirate Roberts refers to an inherited title, with Westley being just the most recent recipient. Pirates weaponized their reputations, with captains like Blackbeard being so synonymous with fear that his legacy lives on to this day. In The Princess Bride, "Dread Pirate Roberts" is known as the man who takes no survivors, and he seemingly cannot die.

Death cannot stop true love. All it can do is delay it for a while. — Westley in The Princess Bride (1987)

By just uttering this name, Westley can win battles without needing to swing his sword. Although he shouldn't be taken lightly, Westley is the gentleman pirate who doesn't have a single bloodthirsty bone in his body. He uses his wit, charm, and gorgeous hair to get out of life-or-death situations, all the while following his heart's desire to find true love.

5 Guybrush Threepwood

The Mightiest Of Pirates

• Debut: The Secret of Monkey Island (1990)
• Captain of the Sea Monkey (and other ships)

From the right mouth, wit can be sharper than a blade. That brings us to Guybrush Threepwood, an upstart pirate who dreams big, cannot swing a sword to save his life, and has the power of the tongue at his disposal. He won't ever outfight anybody, but he can surely insult them into submission. That is the way of the Monkey Island games.

I want to be a mighty pirate! — Threepwood in The Secret of Monkey Island

Scrawny and prone to bursts of cowardice or idiocy, Threepwood sought out a life on the sea because he simply wants to be a pirate. He aspires to be like the figures that outlived the Golden Age of Piracy, but he is really a no-name underdog who stumbles his way through one adventure after another (and one puzzle after another). He isn't Blackbeard, but rather the guy who wants to be Blackbeard.

4 Long John Silver

The Pirate That Started Everything

• Debut: Treasure Island (1883) by Robert Louis Stevenson
• Has been portrayed by Orson Welles, Charlton Heston, Tim Curry, Jack Palance, Lance Henriksen, and Eddie Izzard

Long John Silver drew the map that modern pirates follow. Immortalized through the original book and a billion adaptations that cover everything from cinema to anime, comics, and even music, this humble sea cook is the archetype who set the tropes of a fictional pirate. With a missing leg, a crutch, and a parrot on his shoulder, Long John Silver's look is not only unquestionably iconic, but continues to be referenced to this day. If somebody dresses as a pirate for Halloween, they will likely come as Long John Silver, even if they don't have a specific character in mind.

There's never a man looked me between the eyes and seen a good day a'terwards... — Long John Silver in Treasure Island

Also, make no mistake, Long John Silver has way more to offer than just a legendary aesthetic. In the book and many of the movies, he is a complex figure who can go from a caring mentor to a terrifying monster at the blink of an eye, and he is a master manipulator who even puts the likes of Captain Flint on edge, who has first-hand experience of Silver's ability to sway people to his side. Which other pirate has a fast food restaurant named after them?

3 Captain Jack Sparrow

The Pirate Who Made Pirates Cool Again

• Debut: Pirates of the Caribbean (2003)
• (Former) Captain of the Black Pearl

Long before One Piece broke through in the states and Assassin's Creed embraced the sea, Pirates of the Caribbean showed up and rehabilitated the whole genre (or character type, I guess). A few movies and games aside, pirates were not in vogue in the '90s and early 2000s, but that all changed when Disney decided to adapt a theme park ride and cast Johnny Depp in a supporting role.

Gentlemen, milady, you will always remember this as the day that you almost caught Captain Jack Sparrow. — Sparrow in Pirates of the Caribbean

Introduced in a legendary scene that showcases him as both a genius and an idiot, Jack Sparrow is a captain without a ship, the subject of a mutiny, and the "worst pirate ever," a reputation that he simultaneously lives up to and subverts. Before POTC, cinematic pirates were incapable of escaping from the shadow of Long John Silver, but Sparrow completely broke the mold, all the while retaining the core tenets associated with fictional pirates. Far from a hero, Jack's entire being is defined by his desire to sail the sea forever, and he will do anything to get it done. While the series arguably outstayed its welcome, Jack was the only reason we got 5 POTC movies.

2 Luffy

The Protagonist Of The Most Successful Pirate Story Ever

• Debut: One Piece (1997) by Eiichiro Oda
• Captain of the Straw Hat Pirates

While it needed some time to explode internationally, One Piece has become downright inescapable, with the manga, anime, and live-action adaptation all being huge successes in their own right. No other pirate story comes close to matching One Piece's scale, ambition, and longevity, and that will likely never change. There are roughly 10,000 great OP characters, but Luffy is its face, heart, soul, and energy. Seeking to become the King of the Pirates by finding Gol D. Roger's "One Piece" treasure, the Straw Hats' captain is all about that pirate life, and even his "goal" is merely an excuse to go on adventures with his crew and live the way he wants with no regrets.

I'm not going to conquer anything. The one who is most free... is the Pirate King!!! — Luffy in One Piece manga

In many ways, Luffy is chasing the ultimate romantic ideal of a life on the sea and away from the overbearing hand of a corrupt government. He believes in a world where a person's dreams are far stronger than their upbringing, race, status, or history. He has an innate charisma that regularly turns rivals into either allies or his mortal enemies. In 2026, Luffy is the modern pirate.

Before We Get To Our Number One Pick, Here Are Some Honorable Mentions

• Peter Blood (Captain Blood 1935 movie)
• Tetra (The Legend of Zelda: Wind Waker)
• Revy (Black Lagoon)
• Redbeard (Redbeard comics)
• Miss Fortune (League of Legends)
• Captain Pugwash (Captain Pugwash)
• The Pirate King (The Pirates of Penzance)
• Captain Barbossa (Pirates of the Caribbean)
• About 50 One Piece characters

1 Captain Hook

The Pirate Captain Of All Pirate Captains

• Debut: Peter Pan; or, The Boy Who Wouldn't Grow Up (1904) by J. M. Barrie
• Most Famous Version: Peter Pan (1953)
• Captain of the Jolly Roger
• Has been portrayed by Dustin Hoffman, Jason Isaacs, Garrett Hedlund

If Long John Silver codified the look of a pirate, then Peter Pan's Captain Hook created the myth and cemented its place in pop culture. From his high-society red coat to his obsession with Pan and menacing presence, Hook is the definitive pirate captain AND villain. Even in adaptations that depict him as a goofball who is constantly outwitted by children, Hook still manages to be the most captivating figure in every single scene, often overshadowing Peter Pan himself.

I'll get you for this, Pan, if it's the last thing I do! — Hook in Peter Pan (1953)

Even more so than Long John Silver, Hook is the pirate that all modern interpretations aspire to either be or escape. The original book character is arguably the most famous literary pirate of all time, while his Disney version is comfortably the most famous cinematic pirate of all time. While Luffy and Jack represent the modern era, Hook is the past, blueprint, and legend.