Our Flag Means Death, created by David Jenkins, is a weird and darkly romantic comedy about the golden age of pirates. Specifically, the year is 1717 and the plot—based on a true story– centers on one English aristocrat, Stede Bonnet, played by Rhys 
Darby, who is bored with his life and decides to give it all up to chase his dream of being a pirate. Bonnet, nicknamed “The Gentleman Pirate,” finds his way onto a ship and quickly bonds with a ragtag band of pirates who have been left without a leader. General wackiness ensues as Bonnet’s crash course in pirating is tested when his ship crosses paths with the most famous and vicious pirate of all, Blackbeard, played by Taika Waititi, who, at first, has neither the patience nor the tolerance for Bonnet’s ineptitude. But Blackbeard quickly becomes enamored with Bonnet’s charm and style and the two forge a strong relationship, both professional and personal.
The best way to capture the tone of Our Flag Means Death is by noticing Waititi’s name in the credits. The Oscar-winning writer/director/producer/actor made a name for himself with his irreverently unusual World War II film Jojo Rabbit, in which he played a child’s imaginary Hitler. Waititi furthered his reputation for the offbeat with his fresh and funny Thor: Ragnarok, still the cleverest of all the Marvel films, and the brilliant and critically acclaimed FX series What We Do In the Shadows (one of my all-time favorites). While Waititi did not create Our Flag Means Death, and he only directs one of the eighteen episodes, there is no mistaking the distinct imprint of Waititi’s sensibility on the show. Waititi is the master of blending weird and sweet, mastering the juxtaposition of seemingly incompatible themes and emotions, and bringing an offbeat, sometimes uncomfortable humor to his projects.
Our Flag Means Death is brimming with irreverence and Waititi’s brand of unusual humor, but it is in the mixing in of vulnerability and sensitivity where Our Flag Means Death separates itself from any other run-of-the-mill fish-out-of-water comedy. There is a depth here, in theme, character development and emotion that separates this show from being ordinary. There is absolutely nothing ordinary about this show.
And it all begins with the casting of Darby as Bonnet. Rhys Darby’s performance in Our Flag Means Death is exhilarating and unexpected, reminding me a bit of Anthony Carrigan’s scene-stealing NoHo Hank from HBO’s also brilliant series Barry. Darby, a New Zealand actor best-known for his voiceover work and for co-starring in the series The Flight of the Conchords and Wrecked, truly finds another gear here, as his naturally exuberant demeanor blends perfectly with his character’s optimistic yet naïve confidence. Darby is a true joy to watch in every moment, no matter what he’s doing, but when he is paired with the weirdly offbeat cast of characters that inhabit Our Flag Means Death, it becomes a comedically synergistic miracle.
Our Flag Means Death does feature a cast of seemingly thousands, including many famous cameos and bit parts—some that work, some that do not—and it does take a while for the cast to gel, but once they do, it is magic. Joel Fry and Nathan Foad are particularly strong in their supporting roles, but it is the fantastic Con O’Neill who takes every opportunity to scene steal here—quite a difficult feat when sharing the screen with Darby and Waititi. I generally am not fond of Waititi as an actor, particularly when he’s not reined in, and although there are moments here when he does sink his teeth a little too much into the scenery, he is, for the most part, really strong and he gets better as the show progresses, showing a range and subtlety that I’ve never seen from him.
With all that said, the first episodes are rough and I beseech you to not give up, as the show truly hits its stride about halfway through the first season. I promise you it is worth it to stick with it. The creators obviously needed time to figure out what they had, but, once they figured it out and found their rhythm, it was perfect.
What makes Our Flag Means Death so perfect, and why it took the creators so much time, I assume, to hit their stride, is the fact that it begins as a standard fish-out-of-water comedy about a daffy, classy, educated gentleman trying to get along with a dysfunctional group of dirty, low-class, foul-mouthed, violent and misunderstood pirates, but it finds a way to rise above being standard fare. It could have been so easy to just stay stagnant, reveling in easy jokes and pirate tropes, but the show takes several turns, defying expectation and taking the story into realms you are not expecting, including love—a lot of love, in fact, including same-sex romance, and a lot of it.
The sweetly romantic element of Our Flag Means Death is the most surprising, and the most emotionally rewarding. You find yourself so invested in these characters that you truly care about their feelings and their relationships—it’s ok to get sappy about it, at least that’s what I kept telling myself.
Our Flag Means Death will take you to such unexpected places and explores such unexpected emotions, I encourage you to just let it take you on its weird, wacky and wonderful journey. It is bawdy and naughty, sweet and sensitive, funny and perverse, romantic and dark, but it is also a whole hell of a lot of fun. Eighteen half-hour episodes that were a pure joy. I will never stop missing this show and longing for more.
Both seasons of Our Flag Means Death are currently available on MAX.