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Taika Waititi, in long grey hair and a long grey (hey, wait a second!) beard as the apparently inappropriately named Blackbeard in Our Flag Means Death Photo: Aaron Epstein/HBO Max

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Taika Waititi warns that his pirate show Our Flag Means Death might turn viewers into pirates

‘They’re going to look all the way around, and they’re gonna be like, “Should I… become a pirate? Should I?”’

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People who tune into the HBO Max pirate comedy Our Flag Means Death aren’t going to be surprised by the tone or nature of the humor. Co-stars Taika Waititi and Rhys Darby worked together on the TV series Flight of the Conchords and Waititi’s movies Hunt for the Wilderpeople and What We Do in the Shadows. (Darby, famously, was the profanity-hating leader of the “werewolves, not swearwolves” pack.) The new series shares some of the same subdued absurdist comedy they use in those projects, built around the same kinds of endlessly awkward, puffed-up strivers who have no idea how ridiculous they look to everyone around them. This time, Darby stars as awkward, incompetent pirate captain Stede Bonnet, and Waititi backs him up as his partner and mentor, Edward Teach — aka the notorious pirate Blackbeard.

What may surprise people, though, is that the show’s silly confrontations, outsized characters, and weird story developments are all drawn from real history. Stede Bonnet, the “Gentleman Pirate,” was an actual 18th-century plantation owner who abandoned his wife and children, bought a ship, and declared himself its captain, in spite of his lack of nautical experience. He was notoriously inept at the job, and the records of his career show him repeatedly being wounded, captured, or suborned as captain. He did in fact wind up partnering with Blackbeard, in a troubled relationship seemingly designed to fuel plot twists.

While the historical record marks some of the facts — what ships he looted, when he lost control of his own ship, and so on — there’s relatively little information about the smaller details of his life, or about what happened between him and Blackbeard to cause the various wrinkles in their personal and piratical relationship. Our Flag Means Death creator and showrunner David Jenkins (who also created the 2016 TBS series People of Earth) tells Polygon that the mysteries around their relationship inspired him to turn their lives into a comedy series.

“I saw a really great story with a lot of holes in it,” Jenkins says. “And a great start: This guy has a midlife crisis, and then he blows up his family and his life. And then he becomes a pirate. Which already is a couple of different genres at once — it’s like true crime, mixed with whatever genre ‘midlife crisis’ is. And then he’s bad at it, and then he gets stabbed, and then he meets the world’s greatest pirate, who befriends him. And we don’t know why any of these things happened. Figuring out how to patch those holes in the story — just making it up — was really the reason to do it, in my book.”

In a group interview ahead of the show’s release, Jenkins, Darby, and Waititi (who also executive produced Our Flag and directed its pilot episode) talked to Polygon about their roles on the series, the balance between improv and scripts, and why Waititi thinks the show might inspire other people to ditch their lives and take up piracy — though he advises against it.

This interview has been edited for clarity and concision.

Rhys Darby as fancy-schmancy pirate captain Stede Bonnet and Samson Kayo as his crewman Oluwande in Our Flag Means Death
Rhys Darby as Stede Bonnet and Samson Kayo as his crewman Oluwande
Photo: Jake Giles Netter/HBO Max

Were the rest of you aware of Stede Bonnet before the show started?

Taika Waititi: No, I had never heard of Stede until David told me about him, when we first met over the phone. I’d heard of Blackbeard, but knew nothing about him. And then when I talked to David more about Blackbeard, I got the feeling that I probably shouldn’t bother doing any research. I did a tiny bit, enough to find out no one knew anything about him, and I thought, “That’s perfect. Now I don’t have any homework. Or have to learn an accent!”

Rhys Darby: Yeah, I didn’t really know about the guy, but upon reading a bit about him, he’s very intriguing! This guy’s a huge risk-taker, and something about him lets people believe in him. He’s very troubled. And his drives are the most complicated thing to try and work out. Why did he leave the wife and kids? Why did he go into the most notoriously bad, dangerous profession you could ever do? You think, “He probably won’t survive.” And of course, he didn’t. But he lasted a surprisingly long time, really, for someone who had absolutely no skills, apart from walking in high heels. I wanted to be that person because I knew there were elements of his life that I could relate to — that kind of overconfidence, and no one believing in me.

Waititi: Stede, to a lot of us, is a kind of heroic figure, because he had the balls to do it. I think a lot of people are gonna watch this show and then turn to look at the house around them and say, “This is not my beautiful wife, this is not my beautiful house.” They’re going to look all the way around, and they’re gonna be like, “Should I … become a pirate? Should I?” They’re going to question things about their lives. It’s not to say that they’ve made the wrong decisions to get where they are, but that questioning is a thing we all do. I don’t think you should ever say, “Yeah, I should definitely go and be a pirate.” “Screw up your life and go be a pirate!” is not what the show is saying. But it is tapping into this inherent sense of —

Darby: “Are you happy?”

Waititi: “Have I had enough adventure? Have I actually lived my life?” We all feel that.

David Jenkins: And then there’s a part of it where — wherever you go, there you are.

Waititi: Yeah, you can’t escape yourself.

Jenkins: You’re still gonna be fucked up. You didn’t fix your baggage by running away from it. Stede thought he could outrun his baggage, and you can’t outrun your baggage.

Darby: You take your baggage with you.

Waititi: I’m loving where this is going. You’re dragging the baggage along, and then you get on a boat with the baggage. And the baggage is made out of lead.

Darby: But here’s the thing — he could have dropped all his fancy garments, put on some crappy clothes, and just joined a crew. He would have spoken a lot better than the others, but he could have faked that, and he could have just been a crappy crew member. But he decided “No, I’m going to be the captain!” It doesn’t make any sense!

This show fits so much into the themes of Taika’s work, from What We Do in the Shadows to Thor: Ragnarok, about people self-mythologizing, creating these proud images for themselves that the real world completely undercuts. How did that end up being such a central idea here?

Jenkins: It seems like it appeals to both of us. And I think there’s a lot of overlap in terms of what appeals to us in comedy. Definitely in this, I really like something about a character in existential freefall, because I feel that way. I think everyone feels that way, on some level, and likes to see it reflected onscreen. As opposed to, like, James Bond, who’s invulnerable. Who cares? I don’t care about James Bond. That’s why there are 20 movies about him — anyone can play James Bond. Rhys, you could play James Bond if you wanted.

Darby: Can you make that happen, Taika?

Waititi: Yeah, done.

Jenkins: I think to play someone who is in this much pain, and do it as a comedy — that’s wonderful for me. I think on some level, we all feel like that, and we want to see that reflected onscreen. But I don’t want to see it in a drama. I want to laugh when I see it. I want to feel it, but I want to laugh.

Waititi: Yeah, I echo that. I’m attracted to characters who are just trying desperately to be seen, or to be cool, or just to be pulled in from the margins. And often, when that happens, they realize, “Oh, it was way cooler way out there, way cooler with a small group of my people. We were unique!” So that self-realization, the idea that people always want something more, and then when it’s presented to you, it’s actually one of the worst things, it’s actually the biggest curse you can have — I love those stories.

Jenkins: It’s the oldest story — be careful what you wish for.

Waititi: And the things you’ll sacrifice along the way to what you wish for — your friendships and relationships and the things that made you who you are, the things that made your real friends see you, those are the things you’ll give up to fit in.

An offscreen figure (pssst: It’s Leslie Jones!) holds a knife to Rhys Darby’s nose in Our Flag Means Death Photo: Aaron Epstein/HBO Max

The show is telling a big central story that’s obviously carefully planned, but I’ve also talked to Leslie Jones, who says there was a lot of improv on the set. How did scripting and improv feed into what we’re seeing onscreen?

Jenkins: I don’t think there was enough improv on set! We had an insane schedule, with a huge amount of plot. We were budgeted and designed as a one-hour show, but with a half-hour production schedule, which means we really had to chase these episodes to get them shot. And then there are certain emotional beats that we really needed. So trying to find places to find the fun was hard.

There were wonderful things in there — there was an improvisation between Rhys and Taika at the end of the show where I remember everyone clapped on the set. It was awesome. Taika did some crazy judo move, and it’s in there in its entirety. You try to find those things even while you’re moving forward and trying to advance the characters.

Waititi: That’s the thing — improv still needs to move the scene forward, and move the story forward. It can’t just be two people doing puns on the same theme again and again, which is a very American style of improv that’s kind of pointless. What I’ve found as a director is that there aren’t a lot of people who can actually do it. Some people are just not suited to it. I think it’s actually dangerous to just open it up to every single actor and go, “Let’s improvise!” because it’s just chaos. Everyone gets pissed off with each other, because no one’s listening. So it’s a balance you have to have.

Jenkins: It’s interesting because the cast composition. I really like it when you can build a company of people from different traditions — we have Con O’Neill from Chernobyl, and Rory Kinnear from the James Bond movies, and then people from Saturday Night Live, and then people like Rhys and Taika. And it’s like, everyone’s a little scared of each other when it starts, because —

Waititi: Different gangs coming together.

Jenkins: Everyone comes from a different thing, and they’re like “Oh, shit, you’re really a serious actor!” and “Oh, shit, you’re really funny. I’m not funny!”

Waititi: Oh, here comes the Meisner guy! [In four completely different tones.] Meisner guy! Meisner guy! Meisner guy! Meisner guy!

Taika, after doing so much work as a director, how do you approach something this complicated as an actor?

Waititi: Well, luckily for me, my directing here had finished before I did any acting. That’s a comfort zone for me, directing myself, but I’m starting to feel like I’d prefer to concentrate just on the acting in a given scene. I think I’m better when I do that. When I’m directing, I’ll just give myself the easiest shit to do. A lot of the time when I’m directing, if I’m running out of time, I’ll say “My character doesn’t even need to be in this scene. I dressed up in all this stuff all day for nothing.” [To David.] How was I with the other directors, though?

Jenkins: I thought you were good with them. I mean, it’s intimidating when you’re coming in and directing a director. I was anticipating a little, like, “Euuugh, how’s this gonna go?”

Darby: There were a few times when you were like, “Oh, I wouldn’t have done that.” [General laughter.] Not to the director, but he said that to me.

Waititi: I’d just come up behind them like, “Huh. Mmmkay. Well, that’s … Well, it’s your episode.”

Jenkins: Before “Action!” there was a lot of [Sucks teeth doubtfully.] “Ahhh. Hmm. You’re going to make that choice.”

Darby: I think the two of us can be hard to direct sometimes, when it’s the two of us, when we’re together, because we’re like, “Nah, we know what we’re doing. We know where this is going to go, so just let us do it.”

Waititi: We’re finding a rhythm sometimes, and the director goes, “Cut! Great!” and We’re like, “But … we just, we could feel the electricity! We’re about to create this beautiful little improv baby for you!”

The first three episodes of Our Flag Means Death are now on HBO Max. New episodes drop every Thursday.

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