Learning to Take Risks Like the Queer Pirates in ‘Our Flag Means Death’

Love and connection require emotional risk. After the harrowing nature of the last three years, I needed ‘Our Flag Means Death’ to remind me.

It is the third year of the pandemic, and everyone is talking about pirates.

In my life, particularly, friends of various genders and sexual orientations want to talk to me about Taika Waititi playing the legendary pirate Blackbeard on an HBO Max show called Our Flag Means Death. If you haven’t heard of it, congratulations on having zero nerds in your life. It is the uncool hit show of the year, a half-hour comedy by David Jenkins, and it’s stacked with queer pirates hurling bon mots and homoerotically stabbing each other. Those who love it are possessed by it, because there’s nothing else like it on television. The plot loosely resembles what would have happened if Jack Sparrow’s eyeliner became sentient and joined Muppets Treasure Island. That said, the plot is secondary. The seafaring drag is the draw.

It reminds me of the inexplicable sea shanty era on TikTok, when whaling songs from the 1800s became trendy to sing in collaborative stitched videos. Unlike the more zeitgeisty shows set in our tragic present, like Abbott Elementary, Succession, and White Lotus, Our Flag Means Death is totally divorced from our contemporary reality. Everyone in my corner of the internet has been obsessed with the gay pirates for months. And if we’re maybe a little slap-happy after being inside for so long, at least we’ve found a harmless outlet for our mania.

A lesbian friend periodically leaves me voice memos in which she questions her sexuality: “Am I attracted to dudes now? Or am I specifically attracted to Taika Waititi as Blackbeard?” I cannot help her, but I love listening while she works through it. An ostensibly heterosexual stranger married to a woman writes me a detailed Twitter message about how the queer inclusivity of Our Flag Means Death made him realize he was bisexual. I am a repository for these kinds of musings because, as always, I have no chill, and I make my love for the show publicly known across several platforms. I reassure these friends that being attracted to pirates is perfectly reasonable and normal. We’re all logical, sane adults. There’s just a little bit of madness in the air, and this strain of it is mostly, probably, definitely harmless.

When I finally come down with Covid for the first time, two and a half years into pathological avoidance, I am sick for three weeks around Thanksgiving, during which time I post about rewatching Our Flag Means Death on a near-daily basis. It becomes a bit, sort of, but it’s also deadly serious: After a Paxlovid rebound has me sick for more than the allotted ten days, I need badly to disassociate from my reality. In these dark days, when antisemitic ramblings or mass shootings are pinned on the mental breakdowns of the culprits, I’m grateful that my fantasy life starts and ends with a silly pirate show.

I’m also grateful that this particular internet community considers my DMs a safe space for queer nonsense. As one of those annoying bisexuals who thinks everyone is bisexual, I’ll never blink at a friend’s gay panic. As the joke goes, the pandemic made everyone queerer, and it’s anecdotally true that many if not most of my friends have broadened their definitions of their own gender and sexuality over the past few years. It does make me think, though: What is it about the pirates?

Waititi, not a credited writer on the show, but one of its directors, producers, and stars, posits an answer in an interview with Vanity Fair. Pirates, he says, are “people without any rules . . . it makes perfect sense that they had no rules around sex.” That iconoclastic attitude towards sex and romance tracks through the show, during which three pairs of lovers among the ship’s crew flirt by way of a prosthetic finger, knife-throwing, and swordfighting, respectively. The two leads almost kiss in the moonlight shortly after burning down another ship. Violence, so prevalent on screen as both the means and the end, is in this strange show most often used as kinky foreplay.

In the first heady days of the pandemic, we joked about the roaring twenties that would follow the end of the horror—but three years in, the risk hasn’t evaporated. The party has begun for some, while leaving many behind without a care. We have the inflation and depression that seem inextricably tied to the ’20s, but we’re missing out on the interwar fun they seem to have had a hundred years ago. Reckless drinking and sex make us more vulnerable to diseases that kill, so outlets for revelry are few and far between, with days of fear and isolation the only constant. In 2022, I spent most of the year wondering how we peons, the rabble who keep the country functioning, are still following the rules three years into societal collapse. I suspect I am not alone.

Not incidentally, the fantasy of a pirate’s life, summed up in a song sung by one of the crewmembers in Our Flag Means Death, is one of absence, violence, and transgression: “Oh, a pirate’s life sounds just right / Sounds quite nice, I could say that twice / Sounds quite nice, we won’t live long . . . Smash and gouge and stab and poke / And choke you out, that’s a pirate’s life / Pirate’s life, short, but nice.”

This eruption into no-holds-barred violence sounds deadly, but also desperately appealing with its sly double-entendre. There is an ambient rage in the air. Outside of my window on Skid Row, in downtown Los Angeles, fights break out at all hours. Inside my apartment, I feel like I am supposed to survive Covid so that I can keep working my remote data entry job. Survival is required, but only in service of someone else’s bottom line. The well-meaning messages I get every day urge me to feel better; no one can believe I’m still sick; my supervisor’s patience ran out after a week. The idea of escaping from a white-collar life of obedience in favor of, well, I guess, queer piracy—a life with a greater threat of injury and death but stuffed with excess, evolution, and ecstasy—may be unappealing on its face. But when the former no longer offers longevity or safety, the lure of adventure is obvious.

In early 2022, I quit my office job. I absconded to Los Angeles and took on remote work that is less demanding, less interesting, and less dangerous than a front-facing job that required me to interact with people face-to-face. This deep into the pandemic, I have oriented so many parts of my life around the avoidance of illness that when I get sick, I’m completely at loose ends. What was all of it for? Is the shape my life is in now worth the sacrifices I made to stay safe, now that that safety is compromised? Who am I without my vigilance, my anxiety, my magical thinking? If worry doesn’t head off disaster, what place in my life does worry have? And is it possible that somewhere along the way, I became a coward?

If worry doesn’t head off disaster, what place in my life does worry have?

Pirates, in the mythical sense, are allergic to cowardice. But in Our Flag Means Death, which is first and foremost a half-hour comedy, cowardice is played for laughs. It is punished, and it is ridiculed. It’s a flaw to be overcome, and it’s central to the character arc of the show’s protagonist, Stede Bonnet (played by a very dashing Rhys Darby). What’s the point of fear, the story asks, except in service of vanquishing enemies? Bonnet transforms from a “lily-livered rich boy” to a skilled pirate. His growth shows the limits and the exaltation of fantasy, the true cost and catharsis of leaving one’s comfort zone to become the heroic figure he dreams of being.

Bonnet’s sacrifices aren’t small: He leaves his family and fortune in pursuit of a life he doesn’t understand. He sheds more than his comfort to become a pirate. He sheds blood, sweat, tears. The other pirates on his crew are there for lack of other options; the real Stede Bonnet, on whom the character is based, lived in the early eighteenth century and was a rich landowner in Barbados who had every other option. But bravery is its own reward, at least in the mythos of the show. Moreover, it’s through bravery that the Bonnet of Our Flag Means Death gets almost everything he ever wanted, and even fulfills some desires he hadn’t known how to articulate to himself: He falls in love with Blackbeard, the pirate he thought he wanted to be. In his quest to emulate his hero, whom he perceives to be tougher than him, he finds a man who loves him for the ways he is soft.

Idealized bravery and emotional honesty are central to Waititi’s portrayal of Blackbeard. To his crew, to Bonnet, and to the audience, Blackbeard is the platonic ideal of a pirate, the epitome of a legend. He is not one trope but a dozen in the shape of a character, with an archetype for anyone to latch onto. Our Flag Means Death finds the apocryphal villain occupying a wide spectrum of gender and performance over a handful of episodes. Blackbeard, as second banana, goes on his own dramatic journey of transformation during the first season’s ten-episode arc: He enters the story with literal smoke and fire as he rescues a damsel-like Bonnet from a burning ship, clad in a hypermasculine leather ensemble, appearing every bit the Blackbeard of legend—fierce and pillaging, the perfect foil to Bonnet’s innocent “gentleman pirate.” But when we first meet him, Blackbeard is tired of living up to his own mythology, and so he’s fascinated by Bonnet, a man who gave up a comfortable existence to roam an ocean he is dangerously ill-equipped to navigate. In a twist played for both laughs and pathos, Blackbeard sees Bonnet’s naivete as brave.

As Blackbeard spends more time with the earnest Bonnet, his piratical swagger and bravado are replaced by a different kind of charm. He softens and becomes more “open and available” to his unlikely crew. His competencies as a sailor and as a pirate never change, which seduces both the crew and the audience. (Competence is sexy across gender and sexual preference.) The myth-making of earlier episodes is broken down gradually; in episode six, Blackbeard makes the ridiculous claim that he doesn’t feel fear and, by the end of the episode, is found in a bathtub weeping in terror at a memory of his abusive father. Vulnerability, gradually revealed, is courageous.

I loved watching Blackbeard go from impossibly cool to something more complicated. No one is cool anymore, not now. The pandemic took “disaffected” out of our vocabulary. I’m not sure anyone I know can feign the old ice queen distance, not after the last few years. Instagram stories became deposits of Covid selfies and test results, video diaries, confessionals. Who wants to watch an outfit of the day vlog without a hint of facetiousness now? Even the emerging Gen Z sense of humor, as I’ve witnessed it, relies on a kind of misplaced earnestness that mocks irony.

Maybe Blackbeard became an obsession for the terminally online because his plot so deftly mirrors how the pandemic changed us. Maybe those changes were as much a function of growing up as they were a function of Covid. Blackbeard is first the antagonist, then the comic relief, then eventually the serious romantic co-lead—recognizable life stages in the maturation of my fellow millennials. The final episodes of Our Flag Means Death find him domesticated, quite literally: In the penultimate episode, his beard is shaved and he’s tamed into something resembling a wife, folding clothes for himself and Bonnet after their capture by (and surrender to) the English navy. I recognized that shift. In the past two and a half years, half my friends got married or pushed out pandemic babies. Even before Covid, there was always the frightening possibility that love would somehow transform my vibrant single friends into Stepford wives. I had a fear of that for myself. But every act of giving oneself over to caring and being cared for takes humility and risk; the alternative, it turns out, is unbearable. Connection requires gambling. Blackbeard, like my friends, realized before I did that surrender can be brave.

Maybe Blackbeard became an obsession for the terminally online because his plot so deftly mirrors how the pandemic changed us.

I gave the last three years away to my anxiety. I realize now that I’ve used the pandemic, and my justifiable fear of falling ill, as a way to keep people at arm’s length. Friends and lovers were too risky. Dating was too dangerous. Why would I gamble? But life went on in spite of my fear. A pause button doesn’t exist. Abnegation and agoraphobia may bring me some relief, but they can never bring me joy. When I was sick, I craved the company of other people more than I had when I was well. The obvious hit me. I knew that our only hope of collective survival is community, but I forgot that love and connection require emotional risk. Other people may have learned this before me; I needed Our Flag Means Death to remind me. The most surprising part of the show is that the love story between Blackbeard and Stede, cartoonish figments of a cable sitcom, is played entirely straight.

I don’t find it mysterious that so many people in my life find this iteration of Blackbeard so attractive. Waititi’s portrayal of Blackbeard straddles femme and masc presentations; he wears whatever he wants, not limited to preconceived notions of gender; he lives life with a vim and vigor practically unimaginable to my peers, cowed and disillusioned by our reality. He’s handsome, yes, and also pretty, and also competent, and also vulnerable. There’s truly something for everyone there, but the biggest draw is the courage he demonstrates when he admits to Bonnet that he’s fallen in love with him. We all want to be that brave. The same qualities that attract Blackbeard and Bonnet to one another are the ones we most need from ourselves, and from each other.

I think this is what it is about the pirate show: We want to be both Bonnet and Blackbeard. Right now, I want to be rescued, and I want to do some rescuing. I want to be good at things, and I want to be told it’s not only my utility that makes me worthwhile. I want pretty things, and to be considered pretty—to “wear fine things well,” as the characters do. Pursuing the things and the people you love, especially when you’re out of practice, is liberating. Choosing to love someone gives them the power to hurt you; loving them anyway is brave. Our Flag Means Death offers a unique escape because it’s an entire alternate reality unto itself; the real world, our world, never breaks in. Yet it also delivers us back to ourselves with the reminders of the only things that matter: truth, beauty, freedom, love. There aren’t many shows that offer that kind of enlightened escapism these days, and frankly escapism is the only thing I crave. That, and being a pirate.