The Radical Freedom of Our Flag Means Death

What a long, strange voyage the first season of Our Flag Means Death was. A period comedy that riffs on the biography of Stede Bonnet (Rhys Darby), the so-called Gentleman Pirate who abandoned his wife and children for an outlaw’s life on the high seas, it opened with a few mildly amusing episodes in the Monty Python vein. Then it evolved, unexpectedly, into a tender queer love story that found Stede a soulmate in the notorious Blackbeard (executive producer Taika Waititi). But by the end of the season, Stede had returned home to take responsibility for his estranged family. He and his wife, Mary (Claudia O’Doherty), fake his death so she can inherit his fortune and he can return to Blackbeard. She gets the last words of the season: “To Stede Bonnet: complicated, hard-headed, really quite irritating at times—and now free. May he roam!”

Free is the operative word. More than pirates or LGBTQ romance or maritime history, Max’s Our Flag Means Death is about radical freedom. The universal appeal of that concept might help to explain why the show became one of last year’s biggest surprise hits. It returns Oct. 5, amid impossibly high expectations, for a mostly successful, intermittently inert second season that complicates the liberated bliss of free love with the moral responsibility that comes with free will.

It’s hard to imagine a richer setting, humorous or otherwise, for an exploration of freedom than a pirate ship in the year 1717. Concurrent with the Golden Age of Piracy, on both sides of the Atlantic, was the Age of Enlightenment, when scientific reasoning challenged religious dogma and philosophers such as John Locke, Jean-Jacques Rousseau, and Thomas Hobbes debated how best to balance individual liberty with a social contract that made peaceful civilization possible. Yet as their ideas percolated among the literate elite, society at large remained repressive. Couples like Stede and Mary were all but forced into loveless marriages. Sodomy was punishable by death. And, of course, Britain’s colonial economy hinged on chattel slavery.

Like the Wild West and the 19th-century circus, piracy attracted people—mostly men, but also some bold women—who could not or would not assimilate. Our Flag creator David Jenkins takes this historical reality deep into the realm of unmistakable fiction; as he acknowledged in an interview, “The real Blackbeard was a rapist who handed women over to his crew. The real Stede Bonnet was a slave owner. When we tell these stories, we have to be clear with what we’re doing because all of these people were despicable.” Instead of psychopaths, whose definitional incapacity for emotional growth makes them pretty boring characters, the show’s pirates are misfits warped by bad childhoods and rigid societal roles. “I was just uncomfortable in a married state!” Stede exclaims in the midst of a guilt-driven fever dream. (This turns out to be a paraphrase of something that was actually written about the real Bonnet in his own time.)

When he does find comfort, it’s in the arms of the world’s most fearsome pirate. Weary of adventuring, Blackbeard boards Stede’s ship Revenge planning to kill the captain and steal his aristocratic identity. But before he can do it, they fall, quite slowly and unwittingly, in love. Each palpably treasures what he finds in the other. Blackbeard admires Stede’s odd combination of naïveté and refinement; for Stede, who calls the pirate by his real name, Ed, Blackbeard is everything he’s ever wanted to be. What they share is a restlessness that has caused them to rethink the lives they’ve established for themselves. “You ever feel trapped, like you’re just treading water, waiting to drown?” Ed asks. This isn’t a story about two men coming out as gay. It’s a story in which two individuals, Stede and Ed, realize that they were made for each other.

It is love that (temporarily) liberates them. Piracy is just a means to that end. In the anarchic, cutthroat, casually anachronistic fantasy world Jenkins builds—where Ed and his bitter first mate Izzy (Con O’Neill) dress in bikers’ leathers and the Republic of Pirates is a tourist trap—no pirate would get worked up over an anomaly as benign as two men kissing. Thus the Revenge is a haven for queerness and gender nonconformity. Blackbeard stan Big Pete (Matthew Maher) and Stede’s scribe Lucius Spriggs (Nathan Foad) become boyfriends. The nonbinary actor Vico Ortiz plays Jim Jimenez, who is introduced as a female fugitive disguised as a man but who begins, once their cover is blown, using they/them pronouns. No one raises an eyebrow or requires an explanation. A sweet romance unfolds between Jim and their best friend Oluwande Boodhari (Samson Kayo); in Season 2, Jim has a female admirer. And one of the first season’s only female-identified characters, Leslie Jones’ hilarious tavern owner Spanish Jackie, has 19 husbands and counting.

Love is the most sublime expression of freedom in Our Flag, but, as Jackie’s dominance suggests, it isn’t the only one. Gender roles are as fluid as gender expression in this imaginary past. When Stede returns to Mary at the end of Season 1, he discovers that he was holding her back as well. Having prematurely reported him dead, she’s since found fulfillment hanging with other widows, dressing androgynously, hooking up with her art teacher (Tim Heidecker), and painting Modernist masterpieces about 200 years ahead of their time. Once he’s back, the only way to free her of wifely financial dependence and amicably part ways is to stage a death hoax with many witnesses—cue the elaborate set piece involving a cheetah, a piano, and guest star Kristen Johnston. Liberated women abound in a second season whose most thrilling addition is Mozart in the Jungle’s Ruibo Qian as Zheng Yi Sao, the Chinese pirate queen who, in this time-shifted telling, wields her empathetic ear as a weapon and has a soft spot for Olu.

Not that these free women are necessarily happy. A standout episode casts Minnie Driver and Rachel House as a famous pirate couple who’ve retired, become antique collectors, and are now so desperate to spice up the relationship that they’ve taken to poisoning each other, Phantom Thread style. Their midlife rut mirrors that of Ed, who turns full-on sadistic in the wake of Stede’s disappearance—which happened the night they were supposed to run away together. He’s heartbroken, but more than that, he’s just as purposeless as he was back when he was plotting to kill Stede and usurp his life. Faced with all the freedom in the world and no one to share it with, Ed chooses nihilism. As one character observes, he has to choose: live or die?

Jenkins is taking a risk by navigating into darker waters, and particularly in testing Stede and Ed’s love. Shippers who just want to see dirt-encrusted pirates kiss in the moonlight will have to be patient. Because Our Flag needs real conflict to avoid devolving into sub-Pythonian inanity or fan service. It needs characters endowed with free will to make stomach-churningly awful decisions as well as healthy ones. It needs Ed to backslide so far that he’s forced to confront his worst self. In fact, when the pathos starts to dissipate, midway through the eight-episode season, the story gets almost as bogged down in episodic filler as it did at the beginning of the series’ run. The show is still fun in this mode. It just doesn’t feel as daring, or as liberating, as it can at its best. Our Flag means freedom—and freedom is the opposite of smooth sailing.