While most streaming dramas take forever to get down to business—much to audiences’ justifiable frustration—comedies often require a bit of time to get their feet beneath them, given that their first few episodes are spent establishing characters’ personalities and dynamics so that later ones can then play off those traits and relationships in lunatic fashion.

Judging Our Flag Means Death (March 3, HBO Max) on the basis of its maiden five installments, therefore, isn’t wholly possible, since its introductory chapters are aimed at developing a foundation for forthcoming lunacy. Still, the groundwork laid by creator David Jenkins and executive producer/director/co-star Taika Waititi is a solid one, rife as it is with pirate absurdity made even funnier by the fact that, hard as it is to believe, it’s based on a true story.

Aiming to do for swashbucklers what What We Do in the Shadows did for bloodsuckers, the 10-episode Our Flag Means Death is the tale of Stede Bonnet (Rhys Darby), an 18th century aristocrat who decided in a fit of extreme mid-life crisis insanity to abandon the lap of luxury—and his wife and two children along with it—for rollicking high seas adventure as a pirate. As imagined by Flight of the Conchords vet Darby, Bonnet is a foppish idiot about as cut out to be a buccaneer as I am to be an astrophysicist. Yet a quick internet search proves that his craziness isn’t as far-fetched as it seems, considering that Bonnet was an actual high-society landowner who transformed himself into “the Gentleman Pirate,” an out-of-his-element criminal who eventually clashed with, and then joined forces with, Blackbeard. Consequently, by the time that famed fortune-hunter arrives, played by Waititi himself, the show has taken on a borderline-surrealistic air, thanks to the sheer difficulty of processing that the madness on display has a legitimate connection to the real world.

Fred Armisen and Rhys Darby in Our Flag Means Death


Despite its generally accurate rendering of Bonnet’s personal and professional journey, however, Our Flag Means Death is not a documentary. Jenkins and Waititi’s series is predicated on the unqualified buffoonery of Bonnet, whom Darby embodies as a delusional dandy in embroidered vests, frilly-cuffed shirts, and nicely-coiffed hair. Bonnet is a man-child dilettante play-acting as a scoundrel, and when the show picks up with him, he’s largely won over his collection of hardscrabble men by agreeing to pay them a fair daily wage (which is more reliable than asking them to pillage and plunder for their bounty!) and, also, by showing them compassion and care, such as via daily bedtime readings of Pinocchio during which he does renditions of all the characters’ voices. Frequently retreating to his lavish quarters, which include a full library and two chandeliers, Darby’s Bonnet is a moron clinging to the fantasy that he can pioneer a new, kinder form of pirating, and the actor’s enthusiastic buffoonery is the spark that ignites the proceedings’ wittiest moments.

Bonnet’s men are a ragtag bunch of types struggling, at outset, to carve out unique dispositions. Frenchie (Joel Fry) is a self-interested and scheming crooner, Black Pete (Matthew Maher) is a cocky and mutinous braggart (he claims to have been close to his former employer, the demonic Blackbeard), and Oluwande (Samson Kayo) is an amateur who surmises that this motley crew may be headed for disaster. A mute assassin named Jim (Vico Ortiz) hides a dangerous secret, whereas the homosexuality of scribe Lucius (Nathan Foad) is less mysterious. Weirdo “bird guy” Buttons (Ewen Bremner) is also a bit of a question mark, as is hulking Wee John Feeney (Game of Thrones’ Hodor, Kristian Nairn). Our Flag Means Death takes its time fleshing out each of its players—a natural process for a show built around an ensemble. None of these characters proves an immediate standout, but they each become more amusing as we get to know them better, which bodes well for their voyage’s future.

Initial trouble for Bonnet and company arrives in the figure of Captain Nigel Badminton (Rory Kinnear), an English naval commander far from intimidated by this pirate outfit, who’ve just completed a dim-bulb contest to come up with a terrifying flag. Through a fortuitous twist of fate, Bonnet triumphs in this clash and, in doing so, earns the respect of his ready-to-revolt comrades. While this nonsense is jovial enough, things truly pick up once the protagonist crosses paths with Blackbeard, whom Waititi plays as a ferocious weirdo who also boasts a private desire to be a gentleman. Thus, in Bonnet, he finds both an unlikely mentor and partner, as well as a patsy for his eventual escape from a monotonous pirating existence of ceaseless easy victories. Bonnet, for his part, is eager to strike a deal with Blackbeard, whose legendary success he desperately wants to emulate, and whose friendship helps bolster his own credentials and self-image as a fearsome oceanic tyrant in his own right.

While this nonsense is jovial enough, things truly pick up once the protagonist crosses paths with Blackbeard, whom Waititi plays as a ferocious weirdo who also happens to boast a private desire to be a gentleman.

Darby and Waititi’s bonkers rapport is the mirthful wind in Our Flag Means Death’s sails, propelling it into ludicrous mismatched-buddy-comedy territory. Whether the series intends to keep Waititi’s Blackbeard around for the long haul remains unknown at this point, but on the basis of its early episodes, doing so would be wise, since the show rises to another level whenever the duo share the screen. Nonetheless, there’s also considerable hope that Bonnet’s crew will evolve into a reliable supporting cast, especially as clownish rogues like Black Pete, Frenchie and Oluwande (who feels like the show’s Jim Halpert, knowingly smirking at his compatriots’ inanity) come into their own as three-dimensional characters. Moreover, a handful of cameoing comedy stars (Fred Armisen, Leslie Jones, Nick Kroll, Kristen Schaal) amplify the loopy atmosphere, as well as suggest that additional famous faces are on their way to keep the action lively and ridiculous.

In light of the real-life Bonnet’s exploits, concocting further misadventures for Darby’s “Gentleman Pirate” shouldn’t be an arduous task. Even at present, though, Our Flag Means Death gets considerable mileage from the notion that criminality is a vocation not only for the immoral and the wicked, but for those with a desire for jolly camaraderie, excitement, and danger.

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