How ‘Our Flag Means Death’ Became the Funniest Show on TV

BEHIND THE SCENES

Creator and showrunner David Jenkins breaks down the new season of TV’s most adorable star-crossed pirates.

A photo illustration of Minnie Driver, Taika Waititi, Rhys Darby, and Leslie Jones in ‘Our Flag Means Death’
Photo Illustration by Luis G. Rendon/The Daily Beast/Max

Our Flag Means Death debuted in March 2022 to respectable viewership numbers that grew. And grew. And grew some more. With each week of its 10-episode run, viewership increased, eventually tripling its original audience. The little gay pirate workplace and romantic comedy-cum-historical fantasy that could is back for a second season on Max, and fans will be glad to know that piracy power couple Stede Bonnet (Rhys Darby) and Ed Teach, aka Blackbeard (Academy Award winner Taika Waititi) won’t be parted for long.

The first season of Our Flag Means Death introduced viewers to fictional versions of the real historical figures Stede Bonnet (aka The Gentleman Pirate) and Blackbeard, as well as their respective crews. The two captains instantly forged an unlikely connection. Stede, who decided to exorcize his midlife crisis by abandoning his family and taking to the seas, despite being at best a piracy novice, hero-worships Blackbeard and is thrilled to make his acquaintance. The fearsome Blackbeard, who among friends goes by his real first name, Ed, is taken with Stede’s commitment to enjoying the finer and frillier things in life, marveling at his new friend’s on-ship library and massive, beautiful wardrobe.

While the two captains are an odd couple, each of their crews regards the other as an entirely different species. Aboard the Revenge, Stede reads bedtime stories to his crew and encourages them to use their words when conflicts emerge, while on Blackbeard’s ship, Ed’s first mate Izzy Hands (a deliciously scowling, jealous Con O’Neill) rants that his captain is now a shell of the terrifying legend he used to be. Over time, Blackbeard’s crew begin to appreciate the healthier work-life culture on the Revenge, where there’s room for romantic and collegial dyads to form and pair off.

Of course, the path of true love never runs smooth even for a couple as invested in each other as Stede and Ed. At the end of the first season, the crews are split between ships and land, and Ed believes Stede has permanently abandoned their relationship for his original family, causing a heartbroken Ed to revert to his fearsome Kraken persona. As the second season opens, Stede is frantically trying to get back to Ed and explain that he’s all in on their relationship. Ed’s behavior has been swinging erratically from depressed to murderous, even toward Izzy, and when the two captains and crews meet again, there’s an extra twist: Stede and company have been co-opted by the far more capable and successful Chinese Pirate Queen, Zheng Yi Sao (Ruibo Qian).

Rhys Darby standing in a still from ‘Our Flag Means Death’

Nicola Dove/Max

On the eve of the second season’s three-episode premiere, creator and showrunner David Jenkins reflected on the series’ approach to workplace dynamics, male friendships and romance, and the character arcs he’s most excited for fans to see.

The first three episodes of the season premiere feature a bunch of breakups and reshuffling of romantic and work relationships—not just Stede and Ed. Were you chasing anything in particular, narratively, by splitting up so many dyads?

Definitely. To watch the effects of Stede and Blackbeard’s relationship reverberate through everybody's lives is so interesting. Their separation doesn’t just happen to the two of them, it’s happening to all of them, because they’re a family. Just as the breakup reverberated throughout both crews, getting back together is going to do the same thing.

That makes sense.

The goal was just being true to the character beats and finding ways to make them ring true. Oluwande (Samson Kayo) and Jim (Vico Ortiz, they/them) are friends who got romantic. It rang true to me that they’d watch each others’ lives move forward, and then come back together to find that they still care about each other, and each of them is also happy for the other person. I've seen that happen in real life a bunch of times, but I don't see that dramatized a lot. I think there should be a lot of different flavors of relationships in this show. And there's so many different pairings that you get a lot of chances to be like, “Oh, how are these two different from Stede and Ed?”

How does that relate to your interest in exploring tenderness and vulnerability in male characters? In previous interviews, you’ve referred to Our Flag Means Death as examining the burlesque of masculinity. What does it bring to your work to be exploring it over the course of many hours of storytelling?

That’s an area where Taika’s and my interests overlap a lot. There’s something so understated about his sensibility—I think some of it derives from his New Zealand accent, actually—that suits asking questions about masculinity. And it's fun to look at pirate stories, to play against that genre’s whitewashed, heteronormative conventions. Growing up as a guy, you get a lot of pressure to be just one type of a guy, the guy who refuses to feel things. Men are in terrible trouble in that way. We’re getting better about talking about feelings, but there’s so much more to cover—body dysmorphia, vulnerability, not just talking about feelings, but understanding them and having this whole range of emotions—those are always the things I want to watch.

Do you have favorites among on-screen stories that make room for a broader emotional palette?

Heat and Midnight Run are two really lovely Robert De Niro movies where characters have these very big emotional lives. It’s a similar thing with Robert Redford and Paul Newman in Butch Cassidy and the Sundance Kid. I like extending that. We can push it further, because there's so many different ways to be a man! Not everything has to be a shoot ’em up action thing where people don’t have feelings. A lot of men feel like they need permission to just be their weird selves, to be funny, to dress differently. Try some different things! Maybe wear a color! Put some product in your hair! Don't worry about it, it's gonna be fine. You're gonna be fine.

David Jenkins standing in front of a stand and repeat at Comic Con

Dia Dipasupil/Getty Images

Our Flag Means Death is not a casual show. It’s very funny and playful! But there is not one single frame of the show that plays it cool. As an artist, what’s the significance of qualities like sincerity and earnestness?

I hate coolness, it’s so ungenerous. And I like that you said that it’s not casual. I’m not a casual guy. This is a deeply uncool show. There’s something so special about seeing comedic actors like Rhys or Taika, who are so used to coming into a scene, being incredibly funny and destroying, and then leaving, having to use their earnestness, and not using their weapon of immediately diffusing it by going for a laugh. When I see that, it makes my heart leap. There’s something particularly special about seeing a comedic actor do it.

It’s really fun to watch comedic actors dispel the notion that dramatic acting is 180 degrees away from comedic acting.

Characters that call for that type of performance are a lot of what I love about Robert Altman, Christopher Guest, and Harold Ashby movies. They’re comedies, but those characters really grow and they experience pain, and the pain they feel is real. And then the funny shit that they do is even funnier because of it. Those are the things that bring me the most joy.

Tell me about Zheng Yi Sao, the Pirate Queen. She’s such a good foil for Ed and Stede—her ambition, competence, and leadership style are all so distinct from theirs.

Zheng Yi Sao is the most competent pirate captain on our show, and was the most successful pirate captain in history. She lived about 100 years apart from these fellas, and she was so successful that China had to cut her in and do a treaty with her so she would move on to some other field. She wound up making another fortune in gambling!

One thing that jumped out at me in these first three episodes of the season is how much therapy-literate dialogue is used—where did that come from?

I just think it's funny. The thing about a workplace is that they all see everything that’s going on with others, because they're all on top of each other all the time. I don't want to go l too far with it, but it’s fun that some of these characters can see that one of their friends is in a weird relationship with his boss, and then say “hey, you might want to look at that.”

Where do you think that comes from for the characters themselves?

There’s a level of care on that ship that Stede almost infected them with in the first season, and now those ideas are more alive because of how Stede built the Revenge’s culture. You can see that that spirit is still kind of alive when Jim tells the story of the wooden boy to Bang to calm him down. That’s a little bit of Stede’s kindness being alive in the world still, and of Jim needing and being able to call on it now that everything’s so dark. For them to go from an “every person for themselves” ethos to thinking “there was a time when life meant something on this ship, it doesn’t have to be this way” is interesting growth for the character, and is true to Vico as a person. There's a real kindness to how they carry themselves—they’re one of those people that just makes everybody feel safe. It’s nice to see some of those character traits bleed through to Jim.

Without getting too spoilery, what’s coming up over the rest of this season that you can’t wait for viewers to see?

I’m really excited for Izzy’s journey. Con O’Neill did such beautiful work, and getting to see where that character goes and how he grows, I think is one of the most exciting things of the season. To see where Ed and Stede’s relationship goes is gratifying—to see how they navigate each other and find, hopefully, a more mature way of being together.

Jim's relationships with Archie (Madeleine Sami) and Olu develop, too, and more broadly, the crew coming together as a new kind of family, now that Mom and Dad are getting back together. I also like that Lucius (Nathan Foad) is back, and has an angry young man thing going on that he has to process. For Lucius to go through something really harrowing and have to grow up with it is so interesting, because he had all the answers in the first season.

We can’t not talk about the mermaid sequence at the end of the second episode. How did that come about?

We really have to pick our shots on the show, so that was very storyboarded out. I knew I wanted Kate Bush’s “This Woman’s Work” for the scene, so that was incorporated in it. Unfortunately, Rhys had had a really bad near-drowning experience shooting in a tank before, but I didn’t know that until we were working on the stunts! But when Rhys saw the gorgeous tail, and it looked so cool and beautiful, he decided to go for it. He knew the scene was going to look awesome. So he navigated that costume, which is basically a big flipper that he needed to move his entire core to make it work, and Taika’s there with all this glue to keep his wig on underwater all day. When it’s humming and all the departments are working, everyone feels safe. It gives everyone a feeling of “let’s do it—let’s jump in!”

Leslie Jones and Taika Waititi sitting at a table in a still from 'Our Flag Means Death’

Nicola Dove/Max

Speaking of jumping in, what degree of pressure did you all feel coming into the second season, knowing how high the expectations were from the show’s incredibly passionate fan base?

I don’t feel pressure from the fans, I just feel unconditional love and acceptance, and I think that the writers room feels that too. We all want it to be good, and we want the storylines to be cool. But it’s less pressure, and more just the level of freedom that it gave us, knowing somebody’s watching. It makes doing all the hard work a joy, because you know it’s going to be appreciated. Some people will have critiques, and that’s fine.

I just know that this—the fan reaction to this show—will be the honor of my career. The fan community is so kind and nice and talented—it's just a good vibe, and it’s been safe and affirming for everyone.

We’re all basking in the glow of the adoration of the show from our fanbase. It’s infectious—when we all get together, it saturates every element of the show, and it's a very special thing for all of us.

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