By Jessica Wedemeyer
1:30pm PDT, Sep 19, 2022
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Ahoy! In honor of International Talk Like a Pirate Day on Sept. 19, 2022, Wonderwall.com is taking a look back at the all-time greatest pirates in pop culture, starting with this swashbuckler… Johnny Depp was at his best when he starred as Captain Jack Sparrow in 2003's "Pirates of the Caribbean: The Curse of the Black Pearl." He actually scored an Oscar nomination and two Golden Globe nominations for his performance as the legendary pirate in the beloved film franchise, which is based on a Disneyland ride of the same name. The character is so beloved, in fact, that there have been whispers about the scandal-plagued actor returning to the role in an upcoming sixth installment in the blockbuster series. Savvy?
Now keep reading for more…
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Buttercup wasn't the only one who fell in love with Westley in "The Princess Bride." The farm boy — who was perfectly played by Cary Elwes — became the fourth incarnation of the legendary Dread Pirate Roberts after he was captured at sea by his predecessor. Along the way, Westley picked up some major sword-fighting skills — and an immunity to iocane powder poison — and the rest is pop culture history!
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Dustin Hoffman's portrayal of Captain Hook in the 1991 cult classic "Hook" was the stuff of nightmares — for small children at least! With his perfectly groomed handlebar mustache and wig of black ringlets, Hoffman's Hook was exactly how we pictured the fairytale villain when we were little.
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The crimson pirate? More like the blonde-and-tan pirate! One of our all-time favorite Classic Hollywood leading men — Oscar winner Burt Lancaster — starred as the dashing pirate Captain Vallo in the 1952 adventure-comedy flick "The Crimson Pirate."
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Keira Knightley's Elizabeth Swann in the "Pirates of the Caribbean" franchise is so awesome that by the third installment — 2007's "Pirates of the Caribbean: At World's End" — she becomes not just a pirate, nor the captain of a pirate ship, but the king of ALL pirates. A woman is the Pirate King? We'll raise a bottle of rum to that!
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Tom Sturridge might not have had a peg leg or sent rival buckos to Davy Jones's Locker, but we still loved him as Carl in the 2009 British comedy "Pirate Radio." In the '60s-set film, Carl and his shipmates run a fictitious pirate radio station illegally broadcasting rock and pop music to the United Kingdom from aboard a ship anchored in international waters. Wasn't he adorkable?!
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One-Eyed Willy died long before the titular squad in 1985's "The Goonies" launched their quest to find his hidden treasure. But he still plays an important role in the epic coming-of-age tale — and to that, we tip our tricorn hat! (Mikey — who considers the long-dead pirate to be the first Goonie — is able to save his home with the treasure he recovers from Willy's ship.)
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We never thought we'd have a crush on Captain Hook! In 2012, Colin O'Donoghue joined the cast of ABC's "Once Upon a Time" in its second season as Killian Jones, who becomes known as the pirate captain nicknamed "Hook" after losing a hand. Is it any wonder he won the heart of Jennifer Morrison's Emma Swan?!
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Gene Kelly starred as Serafin — the handsome leader of a traveling circus who poses as the notorious pirate Mack "the Black" Macoco to win the affections of a young woman played by Judy Garland — in the 1948 musical comedy "The Pirate," which scored an Oscar nomination for best score.
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Two years after he won a Tony Award for his performance as the Pirate King in the Broadway revival of Gilbert and Sullivan's "The Pirates of Penzance," Kevin Kline returned to the role in the 1983 big-screen adaptation.
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There's nothing awesome about real-life Somali pirates, but we bow down to actor Barkhad Abdi, who scored an Oscar nomination for his acting debut as the leader of a gang of pirates in 2013's "Captain Phillips."
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In 1996, Tim Curry went toe to toe with the Muppets as Long John Silver in "Muppet Treasure Island." He had us shivering our timbers when he nearly defeated Kermit's Captain Abraham Smollett in a sword fight. Silver was one villain we wouldn't mind throwing overboard!
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Yes, "The Princess and the Pirate" is a bit before our time, but who doesn't love Bob Hope?! The American treasure portrayed cowardly actor Sylvester the Great — who eventually transforms into a swashbuckler of sorts — in the 1944 comedy. Hilarity ensues when Sylvester is forced to impersonate a dastardly pirate captain while caught up in a plot to kidnap a princess and recover buried treasure.
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NBC's "Peter Pan Live!" might have been widely panned, but it was must-see television nonetheless! We especially loved Christopher Walken's bizarre portrayal of Captain Hook in the 2014 live production, during which he forgot his lines on more than one occasion.
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Swoon! "Shameless" alum Zach McGowan is easily one of the most dashingly handsome men to sail the seven seas. He starred as the pirate Captain Charles Vane on the first three seasons of the 2014 Starz series "Black Sails."
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Okay, so they weren't exactly pirates in the traditional sense, but Noah Wyle and Anthony Michael Hall — as Steve Jobs and Bill Gates, respectively — were still pretty great on TNT's 1999 made-for-TV movie "Pirates of Silicon Valley," which scored five Emmy nominations. Just look how cute they were as young tech geeks!
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Hugh Jackman went to the dark side as Blackbeard in 2015's "Pan" — the Joe Wright-directed Captain Hook and Peter Pan origin story. The beloved Australian actor has never looked creepier!
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Oscar winner Charlton Heston looked practically unrecognizable as Long John Silver alongside a young Christian Bale as Jim Hawkins in TNT's 1990 made-for-TV adaptation of "Treasure Island."
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Hugh Grant voiced the Pirate Captain — who tangles with Charles Darwin (David Tennant) and Queen Victoria (Imelda Staunton) over his crew's pet "parrot" Polly, who turns out to be the last living dodo — in 2012's "The Pirates! Band of Misfits." The star-studded stop-motion family film — which was a huge hit with critics and at the box office — scored an Oscar nomination for best animated film in 2013.
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It's one of the greatest comedies of all time: "National Lampoon's Animal House." In the 1978 comedy classic, John Belushi stars as a frat boy named Bluto who dresses up like a pirate to lead the Delta brothers in a mission to sabotage their school's annual homecoming parade.
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Eddie Izzard starred as the one-legged pirate Long John Silver on Sky1's 2012 adaptation of "Treasure Island" — a two-part made-for-TV movie that scored Emmy nominations for its costumes and cinematography.
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Where our "Game of Thrones" fans at?! We'd be remiss if we didn't mention Lucian Msamati, who portrayed Lysene pirate and sellsail Salladhor Saan on three episodes of the hit HBO series. (The character has a much larger role in the series of books on which the show is based.)
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Macklemore and Ryan Lewis shot part of the pirate-themed music video for their hit 2013 single "Can't Hold Us" on the tall ship Lady Washington. But the Grammy winners should've left the swashbuckling to the experts. Macklemore admitted in 2014 that he and many of the music video's extras got violently ill during the at-sea shoot: "I was the sickest I've ever been in my life," he said. Well, we're glad he suffered in the name of art because we LOVE this music video!
