A Pirate Comedy Sails On at HBO

HBO Max’s swashbuckling comedy depicts some real-life pirates in midlife crises

In donning the boots of the legendary Blackbeard, Taika Waititi laments his inability to immerse himself in the pirate experience—to really feel his character’s emotional journey. “I wanted to go Method, but I couldn’t find a time machine,” the actor-director-producer deadpans. “When I go Method, I go back to the year that it was set and live in the 1700s, if I can.”

Waititi may be able to crack wise about the production of this quirky HBO Max period comedy from creator David Jenkins (People of Earth), in which he’s a star as well as a director and exec producer; but the truth is, in the age of COVID, emulating 18th-century hygiene standards—copious spitting included—comes at a risk. And yet? “Art is a risk,” Waititi quips. “We put our lives on the line with this show, in more ways than one. Luckily, none of us got COVID. We had a very strict testing process throughout the shoot, [but] it’s just difficult.”

What wasn’t hard for the Jojo Rabbit Oscar winner was reuniting with fellow New Zealander and frequent collaborator Rhys Darby. “It’s always a dream,” gushes Waititi about working with his What We Do in the Shadows co-star.

“We love working together,” echoes Darby, who leads this new series as Stede Bonnet, who abandons his high-born life to become a Gentleman Pirate. “When you’re making comedy, you want to feel comfortable. The worst thing you can feel is awkward or not get on with certain people, because then you can’t jam. Knowing that we were together meant that we had each other’s support—both through the comedy stuff, which is fun and easy for us, but also the dramatic stuff, which was more of a challenge.”

The dramatic material that grounds the broad humour of the series is, in this case, a deep dive into ye old midlife crisis. “It’s probably a late-life crisis if it’s 300 years ago,” muses 46-year-old Waititi. “But we talked about this. It’s that part of us where we wake up one day and we go, ‘Is this it? Is this what happened to me? Is this my life?’ What happened to, ‘I want to be an astronaut or a fireman.’ At what point did I give up? Is there still time to hold onto some part of life—that fantasy and that dream you had when you were young? It’s also about being wanted. I think a lot of us can identify with this idea of, ‘Are we relevant? Do people even like us?’ ”

The tale of woefully inept pirate Stede Bonnet, absurd as it may be, is actually based in truth. And it was Jenkins’ wife who first heard the story and convinced her husband it would make for an interesting series. Most of the details on Bonnet had to be conjured up by the writers, yet even where there was real historical info available, Jenkins and his team decided not to dig too deeply into Bonnet—or even Blackbeard—beyond broad strokes. “The real Stede Bonnet owned slaves in Barbados during a time where being a slave in Barbados was the worst place you could be. The real Edward Teach [Blackbeard] is not a good guy and not a guy that you’d want to see a show about,” says Jenkins. “We’re already in an alternate reality. We’ve got two people from New Zealand playing Stede Bonnet and Edward Teach. We were like, ‘Let’s stay away from the trauma and go more into the escapism and the fun of it.’ Someone else can deal with the trauma, in something else, if they want to do that.”

That said, even though this is an absurdist comedy, the creator bristles at the word “parody.” Rather, Jenkins explains: “The big thing is, how do you make it credible [as a pirate adventure] and do you have characters that have a recognizable-enough journey that you want to follow them and you can ground it? Then you can make them big and funny and silly, and the thing will hold together. It’s less about making fun of the genre than it is trying to bring new story beats into it that we haven’t seen.”

“And the things that were done really well, don’t do them,” he continues with a chuckle. “I don’t want to compete with Pirates of the Caribbean; they had more money than us, and a couple of those were really good. So you start looking for the things that you haven’t seen. In this [show], it’s funny because it’s daily life—little, minute things. Automatically, I think, when you start looking at teeny-tiny things in a really big genre, it just gets funny—and interesting in a different way.” 

Our Flag Means Death airs Thursdays at 8 p.m. & 8:30 p.m. on Crave1