Our Flag Means Death Season 1 is now available on HBO Max.
Everything about the basic description of HBO Max’s comedy series Our Flag Means Death warns potential viewers, like a Jolly Roger whipping in the wind, that it's not going to be for everyone. But for those who appreciate comedy that sails away from mainstream, this is a wild ride meant with plenty to enjoy.
Loosely based on the life of Stede Bonnet (aka "The Gentleman Pirate”), an actual wealthy, 18th Century landowner from Barbados who left his wife and kids to pillage in Blackbeard’s territory, the series presents its own take on Bonnet’s origin story, warts and all. Season 1 paints him as the most unlikely pirate to ever claim the title, but also an eccentric optimist who, over time, begrudgingly earns some respect from his crew, his peers, and even his family. Smartly, creator David Jenkins (People of Earth), assisted by executive producer/director Taika Waititi, uses Bonnet’s odd footnote in history not as a punchline, but as an aspirational underdog story worthy of celebrating as he punches holes in the pirate genre’s most outdated and worn-thin tropes.
As played by New Zealander Rhys Darby (Jumanji: Welcome to the Jungle), Bonnet is a distracted, starry-eyed dreamer who longs to break the chains of an arranged marriage to Mary (Claudia O'Doherty) and the land-based life forced upon him by familial, class, and financial expectations. The first and fourth episodes, “Pilot” and "Discomfort in a Married State," reveal the frustrations that come from his mocking father and his loveless marriage, and the circumstances that finally spur him to abandon all he knows to set sail on The Revenge, a custom-built ship with living quarters that arguably surpass any pirate ship featured in the entirety of the Pirates of the Caribbean franchise. Surrounded by his beloved silk frocks, massive library, and creature comforts, Bonnet’s glamping version of pirating is as aspirational as it gets. However, functional, it is not.
Having hired a ratty crew who barely tolerates him, Bonnet sails about looking for adventure with no experience or means to navigate the actualities of pirating without immediately getting killed. If not for the kindness of his more sympathetic hires like Oluwande (Samson Kayo), Lucius (Nathan Foad) the records keeper, and eventually the intrigued Blackbeard (Taika Waititi), it’s an understatement to say Bonnet would be sunk.
Much of the fun of the series is watching Darby, festooned in gorgeous silks or silly nightcaps, roam around the boat or out on occasional side trips still acting like the lord of the manor. It’s pure fish-out-of-water storytelling, but Darby goes for it with a charming zeal, instilling his crusty crew with attitude-adjusting exercises to work through their trauma or approrisms to chant them out of their poor negative thinking. His equally weird crew on The Revenge is composed of a gaggle of international comedians and character actors, like Kristian Nairn (Hodor on Game of Thrones), Nat Faxon (Ben and Kate), Guz Khan (Taskmaster), and Joel Fry (Cruella), who all play extremely well against Darby’s brightness, tempering him so the eccentricities don’t go too extreme.
The writers also build investment-worthy B and C stories around many of the supporting players, which broadens out the scope of the series and gives the diverse cast a chance to shine in very unexpected storylines. Vico Ortiz is particularly captivating as a gender-fluid member of The Revenge pursuing their own revenge. And in keeping with the trope-shattering intentions of Our Flag Means Death, the idea of homosexuality not being a real thing on isolated ships at sea for months is rightfully mocked, and same-sex relationships are instead normalized within several charming instances throughout the season. And while the homophobia expected in the genre has to appear, it’s represented by Blackbeard’s proto-pirate first mate Izzy Hands (Con O'Neill), but treated in a very atypical way. His bigotry and bullying are denounced and stripped of their power over and over again so the characters aren’t diminished for whom they love or how they love.
Kudos also to the casting team for landing a murders’ row of big-name comedians from Will Arnett to Kristen Schaal to work within the quirky parameters of the show’s premise. In particular, Our Flag Means Death knew exactly what to do with Leslie Jones’ talent as Spanish Jackie, the frightening, bigamist pirate who has no time for Bonnet’s schtick. She’s perfect in the role and is a worthy adversary for many in the cast.
Another big plus is having Waititi as a main character because it's easy to forget with his more recent heightened character work in JoJo Rabbit and Thor: Ragnarok that the man can act the hell out of those quiet, emotional moments too. Both he and Darby are experts at going big, but reuniting them in this series as polar-opposite pirates with wounded souls allows us to appreciate their beautifully subtle performances, too. Their characters’ relationship gets the slow-burn treatment as they form mutual respect for one another’s pasts and their current approaches to life in episodes like "The Best Revenge Is Dressing Well" and “The Art of Fuckery.” And it's the culmination of that bond that really feeds the emotional climax of the final two episodes, “Act of Grace” and the cliffhanger ending of “Wherever You Go, There You Are.”
Our Flag Means Death isn’t going to be everyone’s cup of grog, but that’s really woven into the DNA of the series as it celebrates the unconventional, the outcasts, and the wanderers looking for their tribes. By the season finale, Bonnet’s folly stitches together a collection of weirdos you can’t help but love and root for with vigor as they show their bravery in embracing their truest selves.