Our Flag Means Death: "Pilot" and "A Damned Man"

(This is the first installment of my biweekly recaps of Our Flag Means Death, the HBO Max comedy series that debuted in March 2022 and quickly discovered an adoring fandom. I’ve never seen it! These recaps are only available to paid subscribers, except this first one, which is available to all.)

• “Pilot” (originally aired March 3, 2022)
• “A Damned Man” (originally aired March 3, 2022)

So I'm reading through a tabletop role-playing game named Thirsty Sword Lesbians at the moment, right? It's hugely acclaimed, having recently won the prestigious ENNIE Award for Game of the Year. I'm just enough of a good critic to know that this game is super well-designed, with a wonderfully deployed, consistent self-conception that extends to every inch of every page. And I know myself just well enough to know that while I would gladly play in a Thirsty Sword Lesbians game, I don't think I would ever be all that into it. Indeed, I would almost certainly bounce off it pretty hard.

We are in a historical moment when a brief window of time where it seemed as though the forces opposing queer people had largely thrown in the towel gave way to a historical moment marked by their Jason Voorhees-esque return from the grave. Just when you thought you were mostly safe to live your life of rainbow-drenched whimsy, here come the social conservatives to tell you you shouldn't.

Simultaneously, we are in an artistic moment filled with stories about people, often queer-coded people, living their lives in small, supportive communities that offer emotional support and space to process trauma. Even media that is not explicitly queer (but may feature queer characters) is full of stories like this, stories like The Good Place or basically every critically acclaimed kids cartoon of the past decade or the novels of Becky Chambers. The appeal of these stories is obvious. Most of us have lived lives where we wish we could find a small, supportive community that offers us emotional support and space to process trauma. In the past, that space was meant to be found within the nuclear family, your local religious body, or your immediate community. But in the 2020s, nuclear families are riven with division, religion is no longer all that central to most American lives, and our communities are increasingly isolated and diffuse.

All of the above applies times 20 for many queer people, who have often been rejected by their families of origin, religious bodies, and communities. The idea of a "found family" trickled into the rest of culture out of queer spaces for a reason: We had to invent our own family units when the world wouldn't listen to us. (I wrote so much more about this here.) So in art depicting the metaphorical or literal formation of these communities, art like Thirsty Sword Lesbians, we can find a lot of comfort and process a lot of pain.

Did I mention how much I struggle with art like this?

Not all of it. I love Chambers's novels, for instance, and I was very jazzed by the first two episodes of Our Flag Means Death (I'm getting there, I promise). But every time I engage with art like this, my hackles go up, and it takes a lot to win me over. It's the contradiction, I think. We are living through a moment when so many of our hard-won freedoms are being stripped away. Therefore, the proper artistic response should be stories that retreat ever so slightly from that problem to offer comfort and support. But what if that retreat reads cowardly, not comforting to the viewer (aka, me)? What if that retreat feels like a lie?

So let's talk about a TV show about some pirates, shall we?

Our Flag Means Death and the strength of allowing your subtext to do the work

‎Until I started this project, the things I knew about Our Flag Means Death were, in total:

1. It was about pirates.
2. Taika Waititi was involved somehow.
3. Two men were in love in a way the internet adored.

Two episodes in, the show has not yet unveiled either Waititi (who directed the pilot but hasn't taken a vital role onscreen yet) or the promised dudes in love arc. And yet you can tell this is a show meant to explore ideas about a space where everybody — including queers, including metaphorical queers — can learn to accept themselves better. It positively emanates off the show, to the degree that I could sort of sense its vibrations in the atmosphere all those months ago when it debuted. "That seems nice," I thought, "but probably not for me."

Yet Our Flag Means Death is a metaphorical found family show with some teeth to it, at least through two episodes. The genius of its conception is that this ad hoc little group exists within a very real historical context (the early 18th century) and amid very real historical figures (including protagonist Stede Bonnet).

Thus, the show's subtext does a lot of work for it. The pirates aboard this little ship are on a literal floating island of tolerance and acceptance, one that is probably at least a little bit ahistorical. (Then again, pirates were often more accepting than others in their society. Maybe this is like when David Milch had the characters on Deadwood use modern curses to convey how shocking contemporaries would have found the language in the camp.) The second they get off the ship, things might go very poorly. But on the ship? They're going to be okay.

What's smart about this is how it essentially fast-tracks the show's very premise. Stede is a guy who just wants to find a place that feels a little more like home, and as such, he's built that home out on the high seas. Even though he's a lousy pirate, he's trying to create a crew that will prop him up to being a halfway almost decent one. And in the process, maybe they'll all come to trust each other along the way.

The series is, in other words, a workplace sitcom. And I love a workplace sitcom.

Another of my maxims about how TV works is that at its core, TV is a medium built atop relationships. That's especially true in long-form TV comedy. If a show runs for hundreds of episodes over a decade or more, it needs to have relationships at its core that will be fruitful to explore for most of that time. (No relationship is fruitful to explore for all of that time.) And that's even more true for the workplace comedy, which can't fall back on tried and true family relationships that have been present in human storytelling for millennia.

The will-they/won't-they, for instance, grew out of the workplace sitcom, because on a workplace sitcom, tossing in a dash of romance was a good way to get people invested in a relationship at or near a show's core. The Office (in all its iterations) became so huge because it so accurately captured a way that lots of people all around the world feel about their bosses.

But the Office example also speaks to the trap of the workplace sitcom. The relationships the characters on that show have with their boss are all individuated, but they're also collective. In the American version, Jim and Pam and Dwight and Ryan all have different relationships with Michael. Still, they're fundamentally expressions of the same relationship, which is a kind of irritation at Michael's power over them. That irritation expresses itself in different ways (Dwight kowtows, while Jim snarks), but it runs through every facet of the show. That ubiquity allowed The Office to become a global hit. And yet also core to that show, in every iteration, has been a will-they/won't-they between a bored salesman and a daydreaming receptionist. If the bad boss stuff hadn't worked, the romance might have still drawn people in. It's a TV trick as old as Cheers.

Our Flag Means Death has taken a page from The Office's playbook. While we're starting to understand how all the pirates relate to one another, the most fundamental relationship in the first two episodes is that of the pirate collective to Stede. Stede is an unlikely pirate captain, being an aristocrat who tried to buy his way into the pirate's life.

He's also an unlikely pirate captain in the show's worldview because he's not a traditionally hard, masculine figure. There's a flashback to how much he loved flowers as a child, and he's clearly doing his best to let his crew make decisions as a collective as much as possible. When he seems to have murdered a man near the end of the first episode, it sends him into paroxysms of guilt, to the degree that the man's ghost haunts him. (That man, Nigel Badminton, was also his chief bully at school. I don't love this storytelling device, as it's very "tell me you're a queer show without telling me you're a queer show," but the series does get at least some mileage out of it.)

All successful workplace sitcoms get you to invest just a little bit in the idea of wanting to work in the setting depicted. I don't actually want to work at Dunder-Mifflin, but I might enjoy hanging out with the employees. And I would love to have a drink at Cheers. But you don't need to buy into Michael Scott or Sam Malone's visions for their workplaces to want to be there.

That's not the case with Our Flag Means Death, a show where the audience is meant to have rather the same relationship with Stede that the other crew members do, I think. We're meant to find him a bit of a curious figure but also to hope that he can pull off the creation of an egalitarian floating community, a found family at sea.

All of which brings me to one last comparison point: Ted Lasso. That show is similarly fascinated with a guy who pushes back against the codes of traditional masculinity in the name of redefining what it means to be a man. But where that show is explicitly about a cishet soccer boy, Our Flag Means Death is already setting up this pirate ship filled almost entirely with men (and one seemingly genderfluid pirate) to be something of a polycule just waiting to happen. There's something queer about Our Flag Means Death, even in the early going, and I find it fascinating to trace what, exactly, indicates that fact to the audience because it's not just the hype.

How I learned to stop worrying and love (this particular example of) tenderqueer nonsense

I've written before about how comfort-food TV often rubs me the wrong way, and many of the shows I touched on in that article are shows that fall under the umbrella of the series I discussed at the start of this article. I think it's great that Schitt's Creek, for instance, imagined a world without homophobia, and I get why so many people need that particular brand of escapism right now. But I, with my evangelical upbringing, see that escapism and think, "Why are you lying to me?" (You can click on the earlier link to go through a more thorough outlining of my feelings on this matter.)

At the heart of most arguments about art, stretching back to the Greeks, is an idea of whether art would do best to depict the world as it is or the world as it should be. We need both kinds of art to function as a society because we need both mirrors and aspirations to truly understand ourselves. Thus, the argument over whether some piece of art is tenderqueer nonsense or not is largely an argument about what you, the audience, most need a work of art to do for you at this moment in time.

It will be interesting to see where Our Flag Means Death takes me in the weeks ahead, but for these first two episodes, I'm impressed by its ability to offer both the world as it is and the world as it should be, albeit in very silly terms. The ship itself is a kind of model of what the world might be like, but once you get off the ship, you find the limitations of that worldview. The other characters the pirates meet confound them or confront them or confuse them. They bump up against a society that finds Stede's entire existence hard to understand. They also represent a society that is actively making the world a worse place to a handful of indigenous people. (More about this in the "Other thoughts I thought" section.)

Our Flag Means Death is lying to me, but all art is lying to me on some level. What's important is that I find the kinds of lies it tells soothing and the truths it alludes to bracing. It's a very funny, overtly ridiculous show. It is not trying to present some ultra-realistic view of either my world or the world of the early 1700s. But its vision of life is sufficiently its own that I'm invested in where all of this is going.

Now when do the boys kiss?

‎Other thoughts I thought:

• Longtime readers will know that I tend not to talk about the jokes in my reviews of comedies, because what am I going to say? "That was funny"? Suffice to say, I smiled a lot watching these episodes and even laughed out loud a few times. It isn't easy to make me laugh, so that's a compliment.
• I found the stuff with the various indigenous characters in the second episode a bit wince-inducing. It was like the show wanted to acknowledge that even at his best, Stede represents a country running rampant over an entire continent where people already lived. And yet it can't just do that. It must also have his charm semi-win over the understandably recalcitrant indigenous folks.
• I've always loved Rhys Darby, and he's absolutely wonderful as Stede. When the first episode opens with him conducting a crew meeting as though he's asking people at a Best Buy for their thoughts on that year's holiday party, I knew I would like this show.
• Other performances I'm vibing with in the early going: Samson Kayo as Oluwande, Vico Ortiz as Jim, and Matthew Maher as Black Pete.
• I appreciate that the show cast a non-binary performer as Jim/Bonifacia, simply because that indicates the show is aware of what it's doing with this character without having to hang a neon sign on it. I like my trans rep best when it's loud by being quiet. (I had a whole metaphor about wearing neon underwear that I cut because it made no sense, but you have to read about the thing I cut to know it existed now. I'm sorry.)
• I do not think fight choreography will be this show's strong suit.
• Creator David Jenkins previously made the very funny TBS series People of Earth, which you should seek out, uh, if you can. (It appears it's on Hulu in the U.S., but these days, one never knows.)

On September 5: Blackbeard shows up, and he looks a lot like Taika Waititi in "A Gentleman Pirate" and "Discomfort in a Married State." If you're not a paid subscriber, you won't be able to read that one. Sorry! (I shouldn't tell you this, but if you only want to buy a single $5 pass to read all of these once they're done, the final article will post on Monday, October 17!)