Rhys Darby captaining a pirate ship in Our Flag Means Death

‘Our Flag Means’ Death Cast Breaks Down What Makes the Heartwarming Pirate Comedy Work

Our Flag Means Death is a comedy about pirates trying to navigate the world of … well, pirating, but having a captain like Stede Bonnet isn’t exactly the best way to go about a pirate’s life. And talking with the cast of the new series showed me exactly why the series works.

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They all understood the history they were telling, the horrors that existed in that time, and used it to inform their characters and their own fictionalized telling of it, and it’s an incredible new comedy from some of our favorite comedians. (I truly love seeing Rhys Darby-led a show.)

https://www.youtube.com/watch?v=xFE8ASwxmpA

Talking with Rhys Darby, he brought up how hard it is to balance comedy and being earnest while playing a character like Stede Bonnet, who isn’t exactly a perfect man. He’s complicated and a mess and abandoned people he loved to go off to be a pirate to prove something to himself, and yet, you still find yourself rooting for him.

Darby said,

Exactly. That’s the tough thing to be able to sort of pull off. And that was the challenge. That’s what really intrigued me because I can do comedy easily. I live and breathe it. I can come in and make scenes, you know, very funny, but the challenge for me was what if you were a bit of a prick and you did that, like what if you had a background that wasn’t quite right. You have to keep remembering that and flash backing and seeing where you came from and am I doing the right thing? And then there was also some very dramatic and emotional moments in the show. And so those were also a challenge to me, sort of acting challenge. And so, you know, it was the best job ever because not only do I get dressed up amazingly and do these amazing scripts that Dave has put together, but I get to challenge myself in those ways. And so can the charming man, it’s the ultimate challenge? Can people still root for me, will they go with me when, you know, clearly, they must be thinking, “ah, really this guy?”

The show also brings to life a queer storyline at the center of the show, something that many have known existed within pirate lore for years but we rarely see explored onscreen. Vico Ortiz plays a fascinating character in Bonifacia, and they talked about joining the show and the excitement to work with such comedy legends while also bringing to life those queer storylines that we know existed.

“I mean, what brought me in was the fact that even though it’s a super funny, very goofy, very silly show, it brings so much warmth and so much depth and it doesn’t shy away of like being pirates, you know, and not just in the violent side, but also in the fact that pirates were like very queer and all of like the way that they approach life. So I was like, yeah, I’m in, count me in it’s my type of show,” Ortiz said, and their costar Samson Kayo also talked about his excitement for his character Oluwande and working with Ortiz.

“I feel like it was very important to understand who we both are as Vico and Samson, before we delve deep into our characters, because then it wouldn’t be genuine,” Kayo said. “And I feel like the fact that we were able to have conversations and open conversations and just like, you know, and stupid conversations as well. Like, it was really, it was really nice to be able to actually know Vico the person and for Vico to know Sam, the person, because then it made our relationship strong immediately.”

Yo-ho yo-ho a pirate’s life for me

What works about Our Flag Means Death is the show’s ability to bring depth to its characters while not shying away from the fact that they are still pirates. Stede is a disaster of a captain, but he has crew like Oluwande who want to try to help, even though they don’t think he should be their leader.

The show balances the horrors of history with a modern take on pirates in a way that genuinely shows that the creators care about the story they’re telling and the history that exists with some of these characters (like Taika Waititi’s Blackbeard), and it’s an exciting new adventure for some of our favorite comedy legends.

Our Flag Means Death premieres on HBO on March 3.

(image: HBO)


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Rachel Leishman
Rachel Leishman (She/Her) is an Assistant Editor at the Mary Sue. She's been a writer professionally since 2016 but was always obsessed with movies and television and writing about them growing up. A lover of Spider-Man and Wanda Maximoff's biggest defender, she has interests in all things nerdy and a cat named Benjamin Wyatt the cat. If you want to talk classic rock music or all things Harrison Ford, she's your girl but her interests span far and wide. Yes, she knows she looks like Florence Pugh. She has multiple podcasts, normally has opinions on any bit of pop culture, and can tell you can actors entire filmography off the top of her head. Her work at the Mary Sue often includes Star Wars, Marvel, DC, movie reviews, and interviews.