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Can This Pirate Comedy Bring Real Romance Back to TV? - Vanity Fair

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The biggest will-they-or-won’t-they of spring TV was between two middle-aged pirates— and when they finally did, they broke decades of disappointing tradition. Can Our Flag Means Death get a second season and keep a good thing going?
Image may contain Clothing Apparel Face Human Person Jacket Coat and Rhys Darby
Rhys Darby and Taika Waititi in Our Flag Means Death.By Aaron Epstein/HBO Max

It’s not a twist, exactly, when HBO Max’s Our Flag Means Death turns out to be a love story. Creator David Jenkins is insistent that the romance between pirates Stede Bonnet (Rhys Darby) and Blackbeard (Taika Waititi) was the center of the show from the very beginning. But for queer viewers who have seen sparks fly between beloved characters only to have it fade away into nothing, the episode nine kiss between the two ship captains was a major event. And it’s hard to blame anyone for being surprised by a full-blown television romance. After all, they hardly exist anymore.

Our Flag Means Death is in many ways a quirky workplace comedy cut from the same cloth as The Office. But the entire first season is structured around Stede and Blackbeard, from their meet-cute shortly after a stabbing to an awkward date on a treasure hunt to that long-awaited clinch. TV shows pair up their characters all the time. Still, it’s hard to think of any recent series that has given so much attention to a classic will-they-or-won’t-they.

Moonlighting is such a satisfying show because you're watching Cybill and Bruce, and are they going to get together?” says Jenkins in a recent Zoom call, referring to what’s become the gold standard of slow-burn TV romance. “I guess there's not many shows where it's the main event.” Adds Darby, “I feel like it was big in the ’80s, and then we fell off the wagon with it. The world's changed so much, and I guess we forgot about romance.”

Internet fandom, with its ships and fan fiction and amazingly detailed fan art, never forgot about romance. Those viewers have embraced Our Flag Means Death with an intensity that has delighted and surprised the people who made it. Darby has encountered adoring fans before, when he was a voice on Netflix’s Voltron series, but “this is tenfold,” he says. “This is unbelievable. And because of the fans, this thing is now surfing so high.” The season ended on March 24, but Darby says he saw the intensity of fan response pick up as the final episodes aired—and one search of #OurFlagMeansDeath on Twitter proves the enthusiasm hasn’t waned.

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Stede and Blackbeard may be the center of the show, but there’s a full supporting cast behind them—including two other boundary-breaking love stories, a nonbinary pirate with a mysterious past (played by nonbinary actor Vico Ortiz), and a raft of guest stars. They all fit, somehow, into the welcoming but still violent world based very, very loosely on the adventures of the real Stede Bonnet and Blackbeard. (They did team up in real life but probably didn’t put more emphasis on teatime and feelings than on looting and plundering.) It’s a show in which Nick Kroll and Kristen Schaal show up as ridiculous French aristocrats and Will Arnett plays a rough-hewn pirate who is also Blackbeard’s ex; it’s also a show with a lot of flashbacks to different characters dealing with childhood trauma. The final episode includes a heartbroken Blackbeard holed up in a pillow fort and Stede faking his death via jaguar. With so much going on, everyone can find something to love.

There are streaming numbers that suggest Our Flag Means Death is outflanking Disney+’s Marvel series Moon Knight (“What is it? Is it a knight who lives in the moon?” Darby teases), though as with any streaming show these days, the true ratings are difficult to pin down. And in our IP-obsessed era, it’s hard to quantify the value of a devoted fanbase, especially for something that isn’t based on any IP other than vague legends about people who lived 300 years ago. Jenkins, circumspect, will only say this: “All the analytics that I can see, say that we're outperforming. And then the analytics that they can't share at the network, you kind of talk to them and they're like, ‘Yeah, yeah, it's good, it's good.’”

Confirmation of a second season, however, remains frustratingly elusive—although, in this reporter’s opinion, Darby and Jenkins don’t sound like guys who are worried they won’t get to continue their story. “I think with the amount of impact the show has had, you'd be stupid not to think, ‘Hmm, wonder where else we should take this thing?’” Darby says. “Like I said earlier on, it's become a phenomenon.” Jenkins, pointing out Darby’s salt-and-pepper stubble, jokes that “Rhys is already growing a season two beard.”

Our Flag Means Death, with its period costumes, huge cast, and numerous stabbings, was not an easy show to make. “We had this beautiful production, and then we had the same amount of time that Barry gets to shoot,” Jenkins says, with plenty of praise for the contemporary, Los Angeles–set HBO show. “Everyone has to put a wig on and everything, so a 10-hour day becomes a 14-hour day by the time you get everybody there.” Darby, who immersed himself in Stede more than any other role he’s played, says he did take the character home with him at the end of the day—“but I was only home for a few hours a night, and they were for sleeping.”

But success, as it so often does, has a way of softening the hard parts. For Jenkins, that meant not just making the show but ensuring he was the right person to make it. He, Waititi, and Darby are all straight men in their 40s—the exact demographic that has shepherded so many of the will-they-or-won’t-they romances in TV history, and also bungled so many of the would-be queer ones. To do things differently, Jenkins knew he needed the right staff to help him. “If you're going to write a show for a modern audience, I think that you need the sociological imagination of a well-rounded room,” he says. “So that you can create something that appeals to more than just a bunch of dudes who are in love with Sopranos—which includes me. If you have a nondiverse room, you're just going to make the same thing over and over.”

To reframe the story about two historical figures who were “monsters” in real life, Jenkins worked with eight additional credited writers— Adam Stein, Eliza Jiménez Cossio, John Mahone, Simone Nathan, Zayre Ferrer, Alex Sherman, Alyssa Lane, and Yvonne Zima—to establish their own pirate lore. “I want buy-in and push-backs and on some level, blessing, with which history we're going to revise and why,” Jenkins says. “And I don't want that to come from a straight white male perspective. I think that's really dangerous.”

Darby credits his teenage sons, in addition to his work on the show, with keeping him up to date on changing norms around gender and sexuality. “I'm so happy that I get to be up to speed with how things are these days and not only know about it but to be in the driver's seat,” he says. “That's the whole thing with this amazing amount of fan art that's come through. I wake up every day and see this stuff, and just to feel like we are doing a really important job of including. I feel really, really proud.”

It’s not hard to guess why lawless, libertine pirates have captured the imagination of generations of men, who have been inspired by their legends to spin macho fantasies from Errol Flynn’s Captain Blood on down. Like Westerns, the pirate movie genre has also been reinterpreted to include more perspectives, like on Starz’s Black Sails. But for virtually everyone who touches it, the promise of pirate life remains the same: you can escape a stultifying society and create your own, making new rules and building a new community on the high seas.

Our Flag Means Death embraces the same fantasy—just from the perspective of this version of Stede Bonnet, who packs his captain’s quarters with books and is introduced in the first episode giving this pep talk to his shipmates: “If someone comes back from the raid mentally devastated, we talk it through as a crew.”

“He's pretty brave to try to live this way,” Jenkins says. “To try to live this dark, strange dream, and to see him doing it in a way that isn't just violence.” Can that utopian, emotionally accessible vision of pirate life continue? Only season two can tell— but if not, there’s always the fan fiction.

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