‘Our Flag Means Death’ Team on Capturing Wee John & Izzy’s Calypso Drag for Episode 6

[Warning: The below contains MAJOR spoilers for Our Flag Means Death Season 2 Episodes 6 “Calypso’s Birthday” and 7 “Man on Fire.”]

Our Flag Means Death‘s crew really knows how to party if the sixth episode from the Max original’s second season is any indication, with the Revenge’s pirates celebrating “Calypso’s Birthday.”

While the installment marked a major milestone in co-captains Stede (Rhys Darby) and Ed’s (Taika Waititi) relationship, the episode also made way for iconic drag moments for Wee John (Kristian Nairn) and Izzy Hands (Con O’Neill). Episode 6 saw Stede and Blackbeard lean into their crew’s request to celebrate Calypso’s Birthday, which is essentially a made-up holiday for the pirate community.

Unaware that they’re being hunted by another infamous pirate, Ned Low (Bronson Pinchot), the Revenge Crew goes all out, making a stop for decorations, booze, and more supplies. Blackbeard even tries to impart some advice to local youths, played by Waititi’s own real-life daughters. As the festivities kick off aboard the Revenge, Stede and Blackbeard sit back and enjoy the crew’s merriment, but the real show begins when Wee John makes his grand entrance as the goddess Calypso.

“I have to say, one of my most joyous costumes that we got to make was at the Calypso [Birthday],” costume designer Gypsy Taylor tells TV Insider. “It’s just a joyous party. They’ve all found flowers from town and made little outfits out of them. And we really wanted Wee John to have a beautiful moment of celebration. We thought, what better way than to put him in drag?”

Descending down the stairs, Wee John makes his grand entrance as the magnetic sea-centric figure with the help of Taylor’s designs. “One of my idols is John Waters, so it was my little ode to Divine,” she says. “So I took the sort of red-pink flamingo dress but made it seafaring. We made it all out of bluey-greeny algae tones, and then there’s alabaster shells that Wee John’s collected. And then he’s made this beautiful feather boa out of all this seaweed and algae, and he’s sort of turned into a seafaring, sea witch version of Divine.”

It was a fun project for Taylor, who gushes, “That might have been one of my most favorite days on set. He’s the most beautiful. I’ve never made anything like this. We had padded boobs, we cinched his waist, and we gave him a big bum and hips. We did the full drag extravaganza, and it was just magic.”

That magic extended to the makeup looks as makeup and hair designer Nancy Hennah notes, “Kristian was just so into that whole drag look. He loved it, and we had a lot of fun getting ready for it.” As for designing the look, Hennah adds that she and her team were “thinking about the colors that they would’ve had access to in that time and how they would’ve got them from the market the day before.”

Despite the intricacy of Wee John’s Calypso, it was Izzy’s drag look that caused a little more workshopping behind the scenes. Inspired by Wee John’s efforts, Izzy follows his lead and dons a more muted, but no less iconic drag look for the party. Explains Hennah, “One of the biggest challenges actually, weirdly, was when we were doing Izzy’s makeup, getting the eyebrows right. We powdered out his face, and we did the lipstick, and that was great, but we went through about four different versions of the eyebrows before we found the right [ones].”

According to Hennah, it was very important to O’Neill that Izzy didn’t “look comedic.” Rather, “he wanted it to be beautiful, and he ended up looking so beautiful in that scene. We had so much fun with it.”

Beyond the look, Izzy’s drag moment was elevated with a gorgeous cover of Edith Piaf’s “La Vie En Rose,” with which he serenades the crew more than once as the crew is briefly interrupted by Ned Low and his crew, who torture the Revenge pirates. Ultimately, the Revenge crew breaks its chains and overpowers Ned Low’s crew, when O’Neill is able to continue his beautiful musical moment.

The romantic tone of the performance is further elaborated as it plays over Blackbeard seeking to comfort Stede after he pushes Ned Low off the boat and is seemingly coping with his first kill. The sequence quickly turns heated as Stede initiates a more physical relationship with Blackbeard.

As for how the song choice came to be, music supervisor Maggie Phillips credits showrunner David Jenkins, saying for her part of the process, “That was more the unsexy part of being a music supervisor, where it comes into clearances and production and how do we figure out how to make it work within the episode.”

Phillips recalls, “It took a while to clear that song. It was just a tricky clearance, not because they didn’t want it, but it was overseas and whenever it’s an international clearance, it’s more difficult and timely.” There was also some back and forth between Jenkins and O’Neill over what version of the song he’d sing.

“He was initially afraid, he was hesitant about singing in French because he didn’t know French,” Phillips explains. “And so we went back and got permission to sing it in English, and while we were waiting for the permission to have him sing it in English, [O’Neill] taught himself how to [sing it] in French.”

“He was still scared to do it,” Phillips shared, “but then it came out, and it was so beautiful. So we ended up using all the French parts of it even though we were cleared for both.” In the end, Phillips says that the moment was “so beautiful,” praising O’Neill: “He’s so good as Izzy.” We couldn’t agree more.

Izzy closes out the final moments of that episode as the Revenge finds itself free of Ned Low’s crew and seemingly smooth waters spread across the horizon. As we see in Episode 7, that peace only lasts so long.

But what did you think of Izzy and Wee John’s epic drag moments in the sixth installment or Stede and Blackbeard’s relationship status update? Let us know in the comments section, below. And don’t miss the Season 2 finale when it drops on October 26.

Our Flag Means Death, Season 2, New Episodes, Thursdays, Max