HBO Max’s series Our Flag Means Death sounds like it was developed specifically with Rhys Darby in mind. The show is very loosely based on Stede Bonnet, a wealthy 18th century landowner who inexplicably abandoned his luxurious life for piracy. Known as “The Gentleman Pirate” (seriously), Bonnet’s brief time as a swashbuckling captain is ideal fodder for a silly retelling. And few seem as perfect to bring his story to life as the man who made the phrase “band meeting” so funny. But the show marks Darby’s first-ever starring role. It’s also the first time he has worked with Taika Waititi— who plays the legendary Blackbeard on the series—without Darby’s longtime friend also directing him.

What’s it like to play another well-meaning but unqualified manager, only this time as a show’s primary star? And is playing around on a big pirate boat with Taika Waititi as fun as it sounds? Those are just a couple of things we asked Darby about after we screened the first five episodes of the series and had a chance to talk with him about playing history’s most ridiculous pirate.

Nerdist: You’re best known for playing Flight of the Conchords’ Murray, but what’s it like being the lead of your own show?

Rhys Darby: It feels good. It feels like it’s the right time. I’ve been in this game for quite a long time now. And even though it kind of doesn’t feel like it, I’m no spring chicken. Conchords was my first TV show. That was my first foray into acting on television. And talk about being in the deep end. That was HBO America. I’d never even been to the states. Now that almost feels like it was a magical dream. But we didn’t know how lucky we had it until we did it. Then we finished two seasons and people were like, “So is there more? What’s happening? It’s so great.” And we’re like, “Well, no, that’s done now.” And then I was like, “Well, what happens now?”

Rhys Darby and Nathan Foad on a boat in Our Flag Means Death
HBO Max

So I carried on with my life. Went back to England, carried on with standup. But the acting bug was there. I felt my whole standup career had been leading to comedic acting, which is what I’ve always wanted to do because I like improvising. I like working with other people. Being a being a standup on stage is fun, but it’s a little monotonous. You don’t get to create with other people and that’s where the real fun is, holding a straight face in front of your friends while they improvise and you try to get through a scene together.

I did other shows after that. Went back to New Zealand, did some stuff there, created my own show. But really I was in with America. I had a good agent. I still have a great manager here in the states. And so they kept saying, “Come back, come back. You’ve got to come back to America.” And Jemaine (Clement), Bret (McKenzie), Taika, and I, we kept at it. We knew that we had something the Americans and the rest of the world enjoyed. So for me, it was just biding my time, keeping myself in the loop.

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Continuing his career in the US included Darby starring on TBS’s Wrecked for three seasons. He says he enjoyed working on the show, which shot in beautiful locales like Puerto Rico and Fiji. But he was far from the series’ lead. At least initially.

RD: I was number seven on that call sheet. Then the Shipley Brothers slowly started to put me into the first position through storylines. I enjoyed, and I’ve always enjoyed, including the movies I’ve done with Taika, being that side character that comes out three or four times during the movie to do some hilarious scene that steals those moments and lifts the vibe of the audience. And that was cool, but I guess my skills caught up with me and I knew one day I’d end up having to be the lead. Now it’s happened. So long story short, it felt like the right time.

The cherry on the top is my mate Taika being there. It just felt like it was meant to happen. That’s why when you see me in that captain role it should fit like a very fancy shoe.

HBO Max

You’re playing a character based on a real person. How much research did you do into the real Stede Bonnet?

RD: I read up on him and it turns out I didn’t really need to. But when you are playing someone real you want to get as much information as you can on them just in case. I didn’t know how historically accurate these guys were going to go. Turns out a little bit, but of course we’re making a comedy series. That gives you so much more poetic license to go right off the rails. Because it was well over 300 years ago we know the basics of the story, but the details are pretty far and few between.

One thing historians do know is that Stede Bonnet was from Barbados. Darby asked the show’s creators if they wanted him to do a Barbados accent, but you won’t be hearing one on the show. 

RD: I kind of knew straight off the back that was not going to be a requirement. You don’t hire Rhys Darby if you don’t want the voice. So that was fine. But other aspects of the character I wanted to really get to grips with was why this person, who had everything, decided to leave it all and go on this ridiculous adventure. I wanted to see if there was anything historically that turned out to be a red flag for obvious reasons why [Bonnet] did this. But there wasn’t anything. And so we really just came down to the idea that we can speculate he was bored and he wasn’t happy in his married life.

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One aspect of the real Bonnet the show does incorporate, with great success, was the Gentleman Pirate’s love of books. Which is only fitting when you realize he was essentially a real-life Don Quixote.

RD: He was an avid reader. It was the thing he did most. He loved reading and had this huge library. And of course it was during the golden age of piracy, so he was reading adventures about these guys out on the high seas who were swashbuckling and killing. And he was like, “God, I want a piece of that.” I think that’s what it sort of came down to.

Darby also found present day inspiration for his character by looking at other well-off individuals who chase adventure in far off places.

RD: I was trying to think about a modern equivalent when you look at someone very wealthy, like Sir Richard Branson. Or even James Cameron, who’s gone, “You know what? I’ve got so much money. I’m going to now buy a submarine and go down to the deepest depths of the universe.” And Richard Branson was at one point in this massive balloon or a plane that circumnavigated the globe. That kind of adventurous spirit is risky as hell. But risk goes hand-in-hand with people who are courageous and people who have got a lot of coin, whether inherited or whether made themselves.

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But it’s like, what have you got to lose? You’ve got literally everything to lose, but you’re one of the few people that have literally got everything. It’s something not many of us will ever be able to feel because none of us are as wealthy as these type of people. But that was a mindset that excited me as well.

At its core this show is about the most ridiculous midlife crisis anybody’s ever had. Are there any elements of your own life that you pull from to play someone having a midlife crisis? Is this something you can relate to in any way?

RD: What I can relate to is that I am that midlife crisis age. And when I go away and work on Wrecked or anything like that, and you are someone who’s been happily married for a long time, something disconnects when you’re away. You’re on your own and all of a sudden you’re a boy again. You’re living in your own hotel room, listening to your own music, not having to worry about your kids. You click into this 20-something feeling again, which is really the best time in your life when you have absolutely no responsibility and you can feel like you’re free. I think for [Stede], having money and having that feeling again, it must have been what drove him to be able to escape and do that.

Of course, these days you can have little flights of fancy. When I go away and stay in a hotel, do some standup shows, or do a series in Fiji, for five minutes I can pretend this is my life. But then you wake up a few days later and you miss your kids. You want the security of your family. You can’t wait to get back. Someone will piss you off or something will go wrong. We kind of explore this in the show as well.

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Darby says one time, very briefly, he considered a years-long undertaking similar to Stede Bonnet’s own adventure. On the longest-of-long shots Darby signed up to be part of a mission to Mars. While he says he never would have actually gone because of his family, he did love the idea of going on such a wild and unexpected adventure.

RD: I thought, “Yeah, I’ll be a guy that could go to Mars.” I wasn’t taking it seriously, because I’m not going to leave my kids, my cat, and my wife, obviously. But you do start to get this little thing in your head going, “I could jump on the spaceship and just go to Mars.” I’m one of these guys that loves reading adventure books and dreaming about stuff like that. I like Star Wars, Indiana Jones, that kind of thing. And I’m a 12-year-old kid in my heart. I can see how that can spark something. Maybe back in those days, when you don’t live that long, [Bonnett] probably thought, “Hell, I’m just going to do it because I really don’t love that woman and these kids.” Some guys aren’t kids people.

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It’s funny you talk about getting to feel like you’re 12 or in your 20s again, because you’re playing someone who’s playing at piracy. Meanwhile you are on these elaborate boat sets wearing ornate costumes with incredible props around you. What’s it like to pretend play at being a pirate yourself?

RD: It’s everything you could imagine.

Taika and I and some of the others would look at each other going, “Oh my God, can you believe we’re 47 and we are now just playing pirates?” And they’ll spend God knows how much money making this ridiculously well-detailed set. You feel almost guilty. We also felt like, “God, when you look at what is surrounding us, we better do a bloody good job here.” It actually lifted our game because we had to act as well as the set, because it was beautiful.

We were like kids in a candy store. But also we knew we had this responsibility. We can’t just f*** around too much. And believe me, people like Taika and I, we will f*** around all day. We’ll go right off script and come up with stupid ideas that need more props. We had to go, “You know what, we’ve got to hold it together and do a bit of play.” But luckily the scripts were so good that we could just do the job. And if this show keeps going, we might get away with a bit more murder next time around.

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You’ve worked for Taika Waititi before (Flight of the Conchords, What We Do in the Shadows), but this is the first time you’re working with him and he’s not directing you. Exactly how much improv is going on? And what’s something about working with him that people might not expect?

RD: Definitely quite a bit of improv going on between him and I specifically. We’ll do a scene together and we’ll always do the scripted stuff first. Then if we feel like there’s something else can add to it we’ll just add it. We won’t even have to ask each other. I’ll just add something and he’ll respond to it, or vice versa, because we expect it.

We really take the moment and see what we can add to it. We just want to make it better. That’s kind of a given.

Now folks will be a little surprised at some of the dramatic tones that end up going of this show. I can’t wait for people to see that because he’s, I mean, has he done much dramatic stuff? I don’t really think so.

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This story, Stede, Blackbeard, you, Taika, the entire cast, the writing, they’re all inherently silly, but the show itself is not as over-the-top silly as a lot of people will expect. What did you do to keep it grounded so that it doesn’t feel like a cartoon but is still funny?

RD: That’s a good question. And yeah, people may be expecting it to be a lot more ridiculous, more like Monty Python, but it has a real gravitas and it has real heart to it. I think that’s what’s going to give it its longevity. People are going to tune in for the silliness, but they won’t be expecting that this is an emotional journey. That’s what I think people are going to really take out of Taika, and hopefully my own, performance. There’s real depth to it. So when we do say silly things, that is just the personalities of these characters.

As humans, we have heart and sorrow. And these characters are absolutely full of that. Both lead characters are deeply damaged people and you can see that. That’s what I’m excited to see is that there are scenes that hopefully are going to make people cry as well. It was fun to act like that because comedy is easy for us. But when we have to get into the touching stuff, that’s when we’re pulling on some new muscles, both of us. I mean, I’ve done a little bit of that with some of the characters I’ve played. There’s a lot of empathy in those guys. But it was cool to explore that for the two of us. And because we’re old friends that made the connection that much more real.

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I think you’ll know I mean this question as a compliment. Why do you think you are so good at playing affable, in-over-their-head buffoons?

RD: I think it’s because I’m an Aries. But I’m on the cusp, 21st of March. As my wife always tells me, “You’re on the cusp,” because she’s a proper Aries. She’s 10th of April and she’s very bossy and very domineering. I’m not majorly into [astrology], but I understand it. I know that I’m in Aries, and so therefore in my friend group I am the one who’s kind of making the decisions or bossing people around, but in a very lighthearted way.

And I’m also a unique person because when I get angry or when I get bossy it’s just ridiculous. No one believes it. Maybe it’s the cusp thing, or maybe it’s because both my parents are very silly, funny people. I have that sense of humor. I think it’s just my general makeup that I do take charge. Some of it comes from my history, cause I’m ex-army. I was in the New Zealand military for four years. I’ve seen and acted alongside and been part of an institution that has authority and I know how to play it. But also really love laughing at it.

The other thing is I’m not as intelligent as I come across. (he laughs) When I was in the part-time soldiers as a cadet back in New Zealand, because I was very silent back in those days—and I still am I’m a very kind, shy guy that doesn’t say much, I’m not overly social at parties unless I’ve had a couple of drinks—the Sergeant major once said to me, “You’re so silent. I don’t know, you’re either one of two things: you’re incredibly smart or you are very dumb.” I’m still trying to work out which one of those guys I am. And I think I take that mindset into those roles, so that first Conchords part was perfect for me. And I think once again here I am as the leader of this rag tag fleet and it’s another perfect fit.

You’re now back at HBO. Taika Waititi is now back at HBO. What would it take to get Bret and Jemaine back to HBO for another season of Flight of the Conchords?

RD: It would definitely take Jemaine wanting it. It’s always down to him and Bret. I’m always there for them to do whatever they want. I’m only ever a phone call away. I will never not want to work with them, never not want to play that character again. But I’ve always been the third and I’ve never made the decisions.

I don’t have any power over that, but I’m really stoked to be working with Taika again now. And Jemaine texted me yesterday. He’s in town. He must want to catch up with me. So the only thing I will ever keep doing is suggesting to Jemaine, “Hey, we should work again soon.”

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With Rhys Darby and Taika Watiti playing two infamous pirates, each equally absurd in their own way, viewers likely won’t be asking about other shows after Our Flag Means Death premieres at HBO Max on March 3. They’ll be asking when the swashbuckling series will get a second season.

But now that Darby is “first” on his own show (one that features a great guest spot from fellow Flight of the Conchords alum Kristen Schaal), we’re confident he has enough sway in his sails to get perfect cameos for both Bret and Jemaine if they want to get the band back together for a silly sea shanty.

Mikey Walsh is a staff writer at Nerdist. You can follow him on Twitter at  @burgermike. And also anywhere someone is ranking the Targaryen kings.