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The pirates of the Revenge standing on the deck of the Revenge cheering under a banner surrounded by flowers Photo: Nicola Dove/Warner Media

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Our Flag Means Death’s Calypso party was designed for you to throw your own

Let loose and celebrate the most ostentatious fake holiday on the calendar

Zosha Millman (she/her) manages TV coverage at Polygon as TV editor, but will happily write about movies, too. She’s been working as a journalist for more than 10 years.

Everybody needs to cut loose every once in a while… especially pirates. The pirate lifestyle is freeing, of course, but it can also be monotonous. That’s why holidays like Calypso’s birthday are so important to slow down and really properly celebrate.

Of course, the joke of episode 6 of Our Flag Means Death season 2, “Calypso’s Birthday,” is that it’s not a real holiday, holy or otherwise. As a bemused Blackbeard (Taika Waititi) has to tell Stede (Rhys Darby) about the crew’s request to honor Calypso with a big bash: “Yeah, they’re just trying to Calypso you. It’s totally just a made-up excuse for a big party.” But, Stede being Stede, he embraces it all the same. And so, the crew sets about throwing a proper Calypso’s birthday soireé — and Our Flag Means Death’s behind-the-scenes crew had to make it all happen.

The primary goal, as anyone working on Our Flag’s production side will tell you, was to make sure things looked as if they could be properly sourced by pirates scouring through a market for impromptu party trimmings.

“We couldn’t get too commercial with our decorations, because they’re still objects that have to look bought and made available at the pirates’ republic floating market,” Ra Vincent, the show’s production designer, says. “So choosing our materials, we were very careful not to make anything too manufactured-looking.”

Still, the party on the Revenge had to tell a story with all its little facets — and in this case, be a bit of a bright light after a very grim time for the crew. “There’s a little bit of a dark streak that runs through season 2, and this was one moment to really celebrate,” Vincent says. “A little moment of joy for those characters — and actually dive a little deeper into kind of who they are as [they are] becoming more fully fledged characters, and finding out what the joyous side is.”

Which meant everyone’s Calypso party look had to not only be a standout, but be full of little details, ones that the camera might only barely catch. After so many episodes of most characters wearing the same outfits, the Our Flag Means Death team made a conscious effort to introduce new elements for the characters to express themselves in a more jovial setting.

The color palette was based on the flowers and fruits in season at the time: things like vibrant bougainvillea flowers or watermelons (though the ones we see in the episode are fake, as it was the end of winter in New Zealand). They used natural dyes for the clothes, which Vincent points out “look better on camera anyway,” but also worked as a nice period touch. And it was important to costume designer Gypsy Taylor that some of the elements of the market be literally stolen — they are pirates, after all.

“Let’s imagine they’ve pinched some flowers, and then they’ve come back and put them in their hats. Or they’ve stolen, like, a pretty little lace thing that they’ve seen and decided to decorate their neck,” Taylor says.

Behind the scenes, Taylor and hair and makeup designer Nancy Hennah made sure everyone’s look was specific to them while still working as a whole unit.

“We went through and lined up the photographs of each fitting to get the different positions of that makeup on their face — to look good as a group, not just a single character,” Hennah says. “We did a lot of practice before we even got the cast.”

For Hennah, Taylor, and Vincent, the character was in the tiny details, even if few of those would be big on-camera moments: The silverware at the table is all mismatched. Blackbeard’s look is close to what he looked like at the end of season 1, to reflect both his inner turmoil and his butterflies around Stede. Hennah and her team worked hard to find grease that would look like the crew might have found it on the boat. Even party-crasher Ned Lowe (Bronson Pinchot) had a look laced with little features that tell a larger story, like Pinchot wanting Ned to look like he was “rotting from the inside out,” a look achieved with the suggestion that he has possibly been sniffing gunpowder. Taylor says her team even made hundreds of fake rats so they could piece them together to make someone a “nice fur jacket,” pirate style.

But the party does have to stop and pay a proper tribute to Calypso, in this case Wee John (Kristian Nairn), who emerges in full drag and looks properly glam.

A behind the scenes sketch of Wee John’s outfit, where an illustration of Kristian Nairn is watercolored over with a mermaid dress and a giant seaweed boa, Divine-like make-up, and a flowing yellow wig
On the left, concept art for Wee John’s Divine-inspired Calypso look; on the right, the finished product in Our Flag Means Death season 2.
Image: Gypsy Taylor/Warner Media
A shot of Wee John (Kristian Nairn) dressed up as Calypso, looking formidable in a mermaid-style dress, with a giant “seaweed” boa wrapped around him Photo: Nicola Dove/Warner Media

If you’re thinking Wee John’s outfit seems hard to source at a pirate market — well, sure, you could argue good tulle is hard to come by on the high seas, and Taylor took a bit of artistic license to put some rhinestones on it as well (“Because, you know, how could I not?”).

But Hennah and Taylor still saw Wee John’s look as one he’d been saving up from things he had access to during his travels. “We knew that earlier we’d had this thing where they found the indigo dust. So we knew there was that blue, we could get a metallic blue [makeup] that could be around, it might have been something that he had saved from whatever,” Hennah says. In her mind, Wee John wanted this almost as much as Nairn: “I think he’s been trying to get in drag for ages!”

(If that’s not enough explanation, consider Vincent’s argument that the show already takes a “broad” approach to historical accuracy, and “giving away historical accuracy to make room for a fantastic theatrical performance” is what Our Flag Means Death is all about.)

It’s just kismet Hennah’s makeup designs worked well with Taylor’s primary inspiration for Wee John’s look: Divine, the legendary drag queen who starred in more than a few of John Waters’ movies.

“I just sort of thought: What’s joyous?” Taylor says. “And then sort of like, Well, look, Ursula [from The Little Mermaid] was inspired by Divine! So I did a full circle moment of Divine to Ursula to Wee John [and] back to Divine.

“And I wanted to do my little ode, my version, which was: If it was going to be Divine but you’re at sea, and you’re only making a drag outfit out of what you can find out in the ocean, we had a giant feather boa out of seaweed.”

It’s not real seaweed; that would’ve been far too fragile to be worn around. But Taylor and her team did construct a very real-looking seaweed boa out of “thousands” of pieces of silicone and fabric. And true to the sourcing nature of the whole Calypso affair, the top of Wee John’s dress is lined with abalone and pāua shells, some of “the only shiny things Wee John had access to.”

In the end, though, Wee John’s grand entrance gets shown up a bit — not by the antagonistic Ned Lowe, but rather by Izzy (Con O’Neill), whose turn for the celebratory gets musical with a performance of “La Vie en Rose.” It’s a moment that Taylor says brought tears to the eyes of many on set: “It was like, full sea enchantress siren, you know?”

But it’s also a moment that O’Neill fought to keep totally sweet and grounded.

A shot of Izzy (Con O’Neill) in his Calypso Party finery Photo: Nicola Dove/Warner Media

“Con really, really wanted Izzy to look beautiful, and for it not to be a sort of comedic look,” Hennah says. “He was really focused on the fact that Izzy’s been going through this process for his character and the love of Blackbeard and all other things that are happening. And he really wanted him to be looking beautiful — and that was really what happened.”

Among the details it was crucial to just right, for both Izzy and Wee John? Eyebrows.

“It took us like four or five goes of completely different eyebrows before we found the right line,” Hennah says. “They just didn’t have the right height, and they didn’t have a sort of… [these] just look softer and more beautiful. They didn’t look like evil eyebrows or funny eyebrows. It was just the most beautiful version.”

It’s the advice she’d give anyone trying to throw their own Calypso party (no matter what day the party falls on, of course): “A good eyeshadow palette with lots of metallics and blues. The eyebrows are very important.”

They may seem small, but these are the details that the Our Flag Means Death crew hoped to provide the crew of the Revenge to help make the world feel more lived in. It feels a little more special under the spell of “Calypso’s Birthday,” where the lighting is always soft and the vibes consistently lovely (except when the ship is being boarded, of course). Even in the flurry of his first kill, Stede gets swept up in the magic of it all, passionately kissing Ed before taking him to bed. But that, too, is the goal of the show, and the relief the Calypso party aimed to provide.

Calypso’s birthday has the juice to make anyone fall in love — just look at those lanterns! But ultimately, Hennah, Taylor, and Vincent underscored that doing your own Calypso party is a personal journey. “Calypso’s Birthday” is just one example of what honoring the most holy day in the “Calypsyan” calendar could be. And the most important thing is always to have fun and be yourself with it.

“If there were another dozen characters with different personalities, Calypso’s party could look quite different but still had the same energy behind it, but with a different aesthetic,” Vincent says. “So it’s all about attitude.”

That said, Vincent did offer one bit of practical advice born from the knowledge of what it takes to rig a set like this: “Scale is what helps these particular parties with their celebrations. They have the ability to hoist decorations up high on masts and, you know, it creates a sense of grandeur. And if you’re able to climb the tree in the backyard and hang your festoons from a safe height, then you’re going to create an environment where you can have a wild rumpus.”