Every September, the internet decides to dust off its “Arrr matey!” jokes and lean into chaos for International Talk Like a Pirate Day. And while most brands will post a half-baked skull emoji and call it a campaign, we’re taking it seriously — because pirates deserve better.
Also, shoutout to Bill Yost — LinkedIn’s very own pirate 🏴☠️. The man’s literally branded himself with the emoji. This list is inspired by him and the fact that he’s been carrying the pirate torch on LinkedIn longer than most of us have been carrying our personal brands.
So grab your peg leg, pour yourself a questionable grog (or LaCroix, no judgment, ok I’m totally judging you), and plunder your streaming service for these five films that will make your Talk Like a Pirate Day binge legendary.
1. Hook (1991)
There are pirates. There is Peter Pan. And there is Robin Williams in the role of a lifetime as a grown-up Peter who forgot how to fly until Rufio — the real star — shows up. Dustin Hoffman as Captain Hook is pure camp theater. His wig deserves its own Oscar.
Why it works today: It’s about rediscovering your inner child — and your inner pirate. Also, you can yell “RU-FI-OOOOOO” in the office Slack and see who the real ones are.
2. The Goonies (1985)
Technically not a pirate movie… until it is. A bunch of kids from Oregon stumble on One-Eyed Willy’s treasure map and end up in a booby-trapped cave straight out of Disneyland. Pirates, chaos, and Sean Astin before Lord of the Rings.
Why it works today: Because it’s about underdogs who win by being feral and sticking together. Also, if you’ve ever yelled “HEY YOU GUYS!” on Zoom, you already know the Goonies are forever. I’m looking at you David Smoak. IYKYK.
3. Pirates of the Caribbean: The Curse of the Black Pearl (2003)
Johnny Depp’s Captain Jack Sparrow redefined the modern pirate — part rockstar, part drunk uncle, part eyeliner model. This first installment is pure swashbuckling chaos with cursed gold, skeleton fights, and Orlando Bloom being hot before Legolas made him hot.
Why it works today: Because Captain Jack’s entire brand is winging it. He’s a personal branding icon: unhinged, unpredictable, and unforgettable. Basically LinkedIn if it wore eyeliner and had a jar of dirt.
4. Pippi Longstocking (1988)
Is Pippi a pirate? Technically, yes. Her dad is a pirate king, and Pippi herself lives feral with a horse and a monkey, flipping adult authority the bird every chance she gets. She’s basically the first influencer — colorful, chaotic, and always doing whatever she wants.
Why it works today: Because Talk Like a Pirate Day isn’t just about eye patches — it’s about channeling that wild, lawless energy. Pippi walked so LinkedIn creators could post chaos.
5. The Princess Bride (1987)
“As you wish.” Inigo Montoya. The ROUS (rodents of unusual size). This film is technically a fairytale but features one of the greatest pirates ever: The Dread Pirate Roberts. Except he’s actually Westley, except he’s actually just a guy in a mask being romantic and stabby.
Why it works today: Because it has everything — pirates, true love, sword fights, and a six-fingered man. Quote it all day and everyone will think you’re charming instead of insufferable. Probably.
Watching these five films is the ultimate way to embrace the chaos, yell “ARRR” at strangers, and remember that pirates aren’t just about treasure — they’re about being unhinged, feral, and free.
So pour the rum (or LaCroix), cue up one of these classics, and let your pirate flag fly. And if you see Bill Yost on LinkedIn — give him a hearty “Arrr,” because the man’s been living this holiday year-round. 🏴☠
And giving an honorable mention to our dear pirate in Dodgeball. How could we forget Steve the Pirate? The man walked into a corporate gym, spoke fluent “Arrr,” and proved once and for all that sometimes the weirdest character is the most unforgettable. Which, if we’re being honest, is the true pirate way.
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