Say hello to your new favorite pirate, Stede Bonnet.
Often referred to as “the Gentleman Pirate,” Stede was a wealthy landowner who upended his life to sail the high seas. His real-life exploits are now the subject of HBO Max’s comedy series Our Flag Means Death, created by David Jenkins and starring Rhys Darby as Stede and Taika Waititi as the infamous Blackbeard.
It was Jenkins’ wife who first told him about Stede’s adventures; she thought it would make a good TV show. One Wikipedia rabbit hole later, and he was hooked. In pursuing a career in piracy, Stede left behind his wife Mary (Claudia O’Doherty) and their children, which Jenkins described as a “world-class midlife crisis.”
“His personal life almost conforms to plot structure,” Jenkins told Mashable in a phone interview. “When you find that within history, it’s amazing.”
“Reading the history of it, you’re like, ‘Alright, how did you get here?'” said Jenkins, “He’s clearly running from his life on land, and it’s just a wonderful question to start with.”
Our Flag Means Death explores Stede’s decision with flashbacks to his childhood and his failing marriage. These elements of tragedy mix with the comedy that comes from Stede being a complete fish out of water in the pirating world. Jenkins described him as an “outsider artist of pirating” and a “class tourist.”
The balance between Stede’s darker past and more humorous present is tricky to get right. But Rhys Darby pulls it off. He plays Stede as relentlessly optimistic about his new life as a pirate, yet haunted by the choices that led him there.
“Stede did a terrible thing to his family. If you cast it wrong, he’s a very hard character to get behind,” Jenkins said. “Very quickly, the only person I thought of for this was Rhys [Darby]. He has this childlike quality that’s endearing.”
Taika Waititi as Blackbeard.
Credit: Aaron Epstein/HBO Max
Joining Darby is Taika Waititi, whose take on Blackbeard is unlike the bloodthirsty versions we’ve seen of him in the past. Jenkins described Waititi’s Blackbeard as having a similar mindset to Bill Murray in Lost in Translation: tired of his life and the legends surrounding him.
“When we were in the room writing it, I just kept hearing [Blackbeard] in [Waititi’s] voice,” said Jenkins. “There’s a mellowness to it that is inherently really funny. I think that Taika has cat energy, and to give Blackbeard this kind of cat energy is fun. It opens him up and you get to do a lot of different things with him.”
“Rhys has dog energy, by the way,” he noted, “Taika has cat energy, and I think that’s why they’re very good together.”
I think that Taika has cat energy, and to give Blackbeard this kind of cat energy is fun.
Darby and Waititi’s interactions are among the highlights of Our Flag Means Death. Their different energies speak to a curious real-life camaraderie, as their two pirates did actually collaborate in the early eighteenth century. “The central thing that makes the show interesting for me is that Blackbeard took Stede under his wing, for some reason, in real life,” Jenkins said. “And it really makes no sense — there’s all these holes in it. Filling those holes in with things of your own invention is one of the joys of doing a true story like this.”
Where Stede is eager to learn about piracy, Blackbeard is weary of it. But in Stede’s strange new “gentleman pirate” ways, Blackbeard finds fresh inspiration for being a pirate. Jenkins explained, “Seeing them discover a need for each other that neither anticipated and charting how that relationship goes is the meat of the story.”
That’s one glorious crew.
Credit: HBO Max
Among the lovable misfits of Stede’s crew is another buccaneer based on a real-life pirate — or two! Beneath a wax nose and false beard, Jim (Vico Ortiz) is a woman named Bonifacia in disguise. Jenkins was inspired by pirates like Mary Read or Anne Bonny, who disguised themselves as men. Jim/Bonifacia’s relationship with gender ends up being one of the season’s most impactful subplots.
“If you’re on this ship, you’re running from something, and you’re running to something that you can’t be on land,” said Jenkins. “It makes sense to me through that lens that there would be somebody who’s pushing against ‘traditional’ relationships or ‘traditional’ ideas of gender.”
“There’s a Bonnie and Clyde quality to this life.”
In fact, one of Jenkins’s favorite pirate facts that he learned while working on Our Flag Means Death was the term matelotage, which was a civil union between same-sex pirates. “The more you look at it,” he explained, “the more you write to the fact that this is a queer-positive world.”
Something else that astounded Jenkins about pirates was “just how fast it all moved — their lives were quite short,” he said. “Your career [in piracy] wasn’t very long.”
Then why would anyone — Stede Bonnet included — become a pirate? “It’s a crime spree,” said Jenkins. “I think that’s what’s interesting about it to me: There’s a Bonnie and Clyde quality to this life, where they just decided to live really hard and die quickly. And wow, what a choice to make.”
Our Flag Means Death debuts on HBO Max Mar. 3, with new episodes weekly.
