For anyone who’s never seen Rob Reiner’s 1987 film The Princess Bride, consider this your spoiler alert. For everyone else, you’ll remember that the Dread Pirate Roberts is actually the nom de guerre of Princess Buttercup’s true love, Westley (Cary Elwes). Though not so dreadful onscreen, as a pirate, he had the reputation of never leaving anyone alive.
9. Pittsburgh Pirates
While the Pittsburgh Pirates haven’t exactly had a successful past, their rich history is full of hope. They played in the first World Series, winning five games and losing two. They were the first Major League Baseball team to be broadcasted over the radio, the first to draft players from India, and the first to win a World Series off a home run, as well as many other notable achievements. With 19 consecutive losing seasons, the Pittsburgh Pirates hopefully have better days ahead, especially now that they’ve earned a spot on our list.
8. Hard Harry / Happy Harry Hard-On
In Pump Up the Volume (1990), Mark Hunter (Christian Slater) is an unassuming high school student by day and a rebellious FM pirate-radio DJ by night. “Hard Harry,” AKA “Happy Harry Hard-On,” extolls his views regularly, railing against what he sees wrong with America and society in general. After being blamed for a listener’s suicide, he challenges everyone to do something about their problems instead of giving in. With the community at large upset about his rabble-rousing, the FCC gets called in to shut him down, but not before he exposes the high school principal as a criminal and inspiring listeners across the nation to voice their own truths.
Edward Teach, also known as Blackbeard, was an infamous English pirate who lived and pillaged during the 18th century. While he may not be as much of a pop-culture icon as the rest of the pirates on our list, we wanted to throw in a “real” pirate for good measure.
6. One-Eyed Willie
In The Goonies (1985), One-Eyed Willie is the driving force behind Mikey and his gang, as they seek to find treasure and escape the evil Fratellis. With no One-Eyed Willie, there would be no movie, and with no movie, there would only be a hollow pit in the heart of every child who grew up in the ’80s. The only thing that fills that hollow pit is the Truffle Shuffle.
5. Elizabeth Swann
Elizabeth Swann of the Pirates of The Caribbean franchise becomes a Captain in the third installment, Pirates of the Caribbean: At World’s End (2007), when she exchanges herself to the pirate Sao Feng for the return of the Black Pearl. Feng hands the reins of his ship over to Swann, who arrives at Shipwreck Cove, and after some heated pirate politics, becomes a Pirate Lord, and later, Pirate King. Without her — and without the her gradual ascension — the swashbuckling days of piracy would have over.
4. Long John Silver
Long John Silver is a fictional character and the primary antagonist in Robert Louis Stevenson’s novel, Treasure Island (1883). It’s also the name of a restaurant chain dishing out a booty of family-sized sea treasures, with a mascot who goes by the nicknames “Barbecue” and the “Sea-Cook.”
3. Jean LaFoote
Taking his name from the real pirate, Jean LaFitte, barefoot fictional pirate Jean LaFoote is always out to steal cereal from his nemesis, Cap’n Horatio Magellan Crunch, better known as Cap’n Crunch.
2. Captain Hook
Antagonist in J. M. Barrie’s Peter Pan (1904), Captain James Hook is a villainous pirate captain of the Jolly Roger brig, and lord of the pirate village in Neverland, where he is widely feared. Peter Pan’s archenemy was supposedly Blackbeard’s boatswain, and the only man Long John Silver ever feared. Captain Hook’s two fears are the sight of his own blood (which is supposedly an unnatural color), and a single fateful crocodile.
1. The Pirate Party
The newest political party to have representatives in Germany’s state parliament, the Pirate Party ousted the Free Democrats after recently winning nearly 10% of the vote for the Berlin state parliament. Because the party’s agenda is all about Internet freedom, we’re awarding the Pirate Party our number one spot on our list.