What Jack Sparrow Can Teach Your Boys About Masculinity

My favorite movie scene as a writer is from Pirates of the Caribbean.

A Disney movie filled with goofy dialogue and primitive physical comedy, yes.

But behind the shiny objects that dazzle the kiddies and sell tickets is a strong development of Jack Sparrow’s character and a pretty tasty dive into the essence of masculinity.

Jack Sparrow isn’t a typical character from the Disney repertoire of beauty/beast and princess/knight. In fact, I’d wager the average viewer wouldn’t call him masculine or a ‘hero’ at all. He doesn’t seem to have a killer instinct or willingness to fight. He loves big hats and waves his arms wildly as he runs (which is often) from trouble and threats. The guy is wearing a pound of eyeliner, and not for stage makeup’s sake.

And yet, I am unwavering in my belief that he is the most masculine character a Disney writer has ever penned.

If you take a look at the opening scene – the sequence of the series – we are zoomed in on Jack’s stoic and majestic face as he looks to the horizon (clearly atop a sailboat mast). Power, strength, and focus are projected as the music swells. Our hero.

Then, with a clever zoom out, it’s revealed that this majestic ship is a mere tattered sailing dinghy… that’s sinking.

Jack’s expression snaps to reality, and he drops to the base and begins bailing water out enthusiastically. This shows us a real and vulnerable, the ‘behind the scenes’ of an accomplished sailor.

And then, a grave warning. The skeletons of hanged pirates flap in the breeze right in front of Jack’s little sloop.

Jack immediately removes his hat in a show of respect for these fallen brothers, despite the fact that he’s got an emergency on his hands (sinking boat).

This demonstrates a fierce loyalty to some kind of set of internal standards, honor, a code later referenced.

In the final shot of our intro sequence, the music crescendos, and Jack is again atop the mast. The boat has already sunk below the water, and his mast is all that remains dry as he approaches the dock.

Right as the top of the mast is about to be overtaken by the dark harbor water, Jack reaches the dock and casually steps off just in time. He strides down the dock without a care for his lost sailboat or even a glance backward.

In this moment, he moves forward towards some goal (though it isn’t clear yet what) and he isn’t bothered by lost money in the boat or his frantic sinking experience.

I think the viewer can feel his complete confidence and ease that the future problems will be sorted as they arise.

Jack has taken a situation most would deem as negative, scary, or embarrassing and glided through it with an almost slight self-deprecating flourish. This is pure masculinity.

This is the part of masculinity that doesn’t get celebrated for the magic it contains. We cite Rocky, Rambo, Schwarzenegger as giants in the world of masculine men. And strength, the ability to take a physical beating (and give it back), is part of the equation. The rest, however, is more nuanced.

It’s about charging into the unknown, unprepared and maybe even scared shitless… but with a sly grin.

This is the real swagger of masculinity. Not arrogance exactly, but an unwavering self-belief in one’s own competence. Confidence says “I have the ability to do X.” Competence says “Whatever comes up, I’ve got what it takes to handle it” or rather… “I’ll be okay no matter what comes.” In this regard, the scrawny idealistic kid from ** is every inch the man and a tough guy John Wayne.

When young men are taught how to “be a man” or more recently “how not to be a toxic man,” there’s really no mention of this part, this essence. But there should be.

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