Truth be told, you had me at pirates and Rhys Darby. Sprinkle in a little Taika Waititi as a co-star and execute producer, and “Our Flag Means Death” feels like a can’t miss outing from HBO Max. That’s a lot of pressure on everyone involved to deliver on such high expectations. Fortunately, the new series fires on all cylinders right out of the gate and never lets up.
Deeply funny and satirical, “Our Flag Means Death” feels a lot like “What We Do in The Shadows,” but for pirates. And that’s a good thing, as both shows perfectly balance that deadpan delivery juxtaposed against the absurdity of situations. Pirates actually feels even more freeing, loaded with the ability to poke fun at both history and fiction simultaneously. “Our Flag Means Death” is the perfect satire that scratches the itch left in the wake of the wildly successful “Peacemaker.”
Created and written by David Jenkins, “Our Flag Means Death” is a six-episode comedy series that follows Stede Bonnet, a wealthy aristocrat who leaves his wife and children behind to pursue a life of piracy. Known as The Gentleman Pirate, his cushy life makes him a rather poor pirate captain, who is consistently disrespected by his crew as well as constantly getting everyone into the worst situations imaginable. Before long, he inadvertently befriends the feared Blackbeard, who offers to teach him the ways of piracy if Bonnet will teach him the ways of the gentleman.

While Bonnet was in fact a real person, the series ramps up the satire to 11, with Darby playing The Gentle Pirate with complete affable abandon. The series blends historical events with a healthy dose of satire. “Our Flag Means Death” brilliantly plays with history, exaggerating our misconceptions and long standing interpretations of the pirate life. It not only helps that this is all lead by Darby, who has proven time and time again that no one plays it straight even when the joke is on him better. But the supporting cast is also terrific, with Matthew Maher as Black Pete, Joel Fry as Frenchie, Sampson Kayo as Oluwande, Ewen Bremner as Buttons and many more familiar comedic faces as the crew all giving it their all here. The series also features guest appearances from Leslie Jones, Fred Armisen, Nick Kroll and Kristen Schaal. Oh yeah, and Waititi as Blackbeard is the nail to hammer it all home.
The casting (minus Armisen, who I simply cannot get behind and find his comedic delivery and timing to be abysmal and unfunny at every turn) is as close to perfect as you can get for something like this, and “Our Flag Means Death” looks and feels like everyone is having as much fun making it as we are watching it. What also sets the show apart from other attempts is again, in like with something like “What we Do in the Shadows,” there is a balance of purposeful narrative that is what drives the ridiculousness. For what should feel like a collection of silly sketches featuring pirates, “Our Flag Means Death” manages to unify them all with a story loosely based on actual history. This allows the show to be as unanchored as it wants to be without ever getting lost at sea.

There is a fine line between fictionalized history and satire, and “Our Flag Means Death” manages to give validity to both without ever feeling imbalanced. It seems to be having just as much fun playing with history and historical inaccuracies as it does satirizing them with over the top, ridiculous characters. The series isn’t necessarily laugh out loud funny, but it is consistently funny and even more engaging as all of the characters but hero and villain are interesting and unique. They all have their own schtick in one way or another, and there really isn’t a weak link. It is situationally funny, and it never really lets up. Whether it’s Bonnet walking through the streets of the Pirate Hangout shouting “Booty for sale” or trying to explain vacation to his crew to Black Pete’s insistence that he was once Blackbeard’s right hand man, it all works and is always funny.
I really don’t know that I have any real complaints about “Our Flag Means Death.” Like I said, it fills the void of a show I love that is wrapped up its first season and is in the same vein of a show I absolutely adore. There’s really nothing to dislike, unless somehow Armisen becomes a main character. I’m sorry, I just don’t like him as a comedic actor. I never have, truthfully, and while he’s extremely tapered down here (which is refreshing), the less of him the better for me.
If you’re looking for a solid comedic outing on streaming, I highly recommend “Our Flag Means Death.”
Now if you’ll excuse me, I need to go make sure my cats are witches that steal children.
Rating: 4 out of 5 Stars
“Our Flag Means Death” is currently streaming on HBO Max, with new episodes airing every Thursday. You can watch the trailer below.
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