Midlife crises manifest as many things, and in HBO Max’s Our Flag Means Death, Stede Bonnet (Rhys Darby) checks off all the usual criteria. A flashy new vehicle? Yep. A flashy new relationship? Of sorts. A drastic career change? Well, that’s an understatement.
Created by David Jenkins, the 10-episode historical adventure comedy follows the aftermath of Bonnet leaving his cushy life to become a pirate during the Golden Age of Piracy. His aristocratic background and penchant for the finer things in life eventually earns him the moniker “The Gentleman’s Pirate.” This is a man who drinks tea with seven sugars and keeps a roaring fire going in his chambers, never mind that he’s on a wooden ship. Best of all, Bonnet really did exist in one of those stranger-than-fiction historical gems that sounds straight out of an improv troupe’s sketch.
To save you the Wikipedia trip: A wealthy landowner in Barbados, Bonnet abandoned his wife and children for a pirate’s life despite his ineptitude at sea, and did a notoriously terrible job. He stumbled into a collaboration of sorts with the already famous Blackbeard that ended poorly and earned the derision of his crew. Naturally, Jenkins takes plenty of creative liberties with his vision—and for good reason, as the real Bonnet’s high-seas jaunt only lasted an unceremonious 18 or so months before his capture and subsequent execution.
Our Flag Means Death kicks off in 1717 after Bonnet has already left his home and cobbled together a crew for his new ship, The Revenge. (His backstory gets gradually parceled out via flashbacks.) Darby’s fellow New Zealander Taika Waititi stars as Blackbeard, and also executive produces and directs the pilot episode. Waititi’s presence and the fish-out-of-water concept quickly bring to mind What We Do In The Shadows, but office dynamics provide a better entry point into the series. “Pirate workplace comedy” is one of those phrases that’s so instantly evocative, it’s hard to imagine why the idea hasn’t been done before.
Darby serves as the show’s fallible heart, tapping his experience as hapless manager Murray Hewitt in Flight of the Conchords. Here, his incompetent boss comes across less Michael Scott and more Ted Lasso, emulating an especially Lasso-esque mentality of wanting his crew to grow as people, not just pirates. He assigns art projects, tells bedtime stories with silly voices, and teaches the importance of leisure time. Fond of catchy rhymes, he strives for emotional intelligence on his ship: “We talk it through as a crew.” Of course, unpacking toxic masculinity plays out a little differently on a 18th century ship whose “ballroom” really just stores cannonballs. Bonnet’s sensibilities don’t just make him an odd duck, but a liability and a target for possible mutiny, especially when paired with pirates whose perfect vacation consists of torturing prisoners.
Why would bloodthirsty pirates stick it out with a “weak-hearted, soft-handed, lily-livered little rich boy?” Breaking from tradition, Bonnet pays his crew a weekly salary, regardless of how much swashbuckling they do. Plus, his crew isn’t the most competent bunch either. Such a high-risk vocation attracts some oddballs. The show’s also smart to acknowledge that some members, like Oluwande (Samson Kayo), a Black man, aren’t enamored with the gnarlier aspects of the job, but recognize piracy as one of the better options in a world that offers little. (And it’s true that some pirate ships established surprisingly egalitarian societies for the time, adding a grain of reality to Bonnet’s dream of a piracy ship free from abuse.)
Our Flag Means Death mines much of its early comedy through casting a modern lens toward historical happenings. Nick Kroll, Leslie Jones, and Fred Armisen pop up as guest stars, while Kayo, Joel Fry, and Nathan Foad especially shine in their roles as crew members. Not all the dialogue lands though, and the writing is particularly uneven in the early episodes—neither consistently funny or sharp enough to live up to the cast’s merits. Pacing issues similarly plague the series. The roughly half-hour episode runtimes suit the show, but the comedic setups stretch too thin in the early chapters. The much stronger second half has more character-driven humor and a meatier plot, but plot points that could easily command a whole episode get rushed through, making key character developments also feel hasty.
Waititi’s early arrival to The Revenge signals a key shift—Blackbeard’s inherently a showy role, yet Waititi channels the legend less with maniacal laughter and more with the magnetic intensity of a man used to commanding attention, no matter what he does. He imbues the character with a world-weariness as he ponders a most decidedly un-Blackbeard concept: retirement. Bonnet and Blackbeard find common ground through their respective midlife crises. The former torpedoed his life based on dreams for adventure, while the latter’s bored by his perfect track record and frustrated with the overblown tales of his exploits (“I have one gun, one knife, just like everyone else!”). Down to their respective outfits of colorful silk robes and all-black leather, the pair provide entertaining foils to one another. Darby and Waititi riff off each with glee, perfectly suited to this anthropomorphization of an unlikely animal friendship. Just like a gator befriending a kitten, there’s a degree of danger involved.
Blackbeard’s presence first feels like a double-edged sword though. He sucks crucial time away from Bonnet’s relationships with the rest of The Revenge’s crew, who have scarcely had enough screen time for the audience to learn everyone’s names. The sharp swerve from workplace comedy to buddy comedy initially feels muddled, like the show isn’t sure of its identity. But Jenkins’ intentions with the character become clearer and more compelling over the course of the season. It takes some growing pains, but he ultimately strikes a satisfying balance between exploring Blackbeard and Bonnet’s supercharged bond and adding dimension to supporting players.
By exploring interesting character dynamics, Our Flag Means Death finds a way to evolve beyond the premise’s novelty. Jenkins embraces a mishmash of genres for his ruminations on self-discovery, and what it means to find happiness through the unexpected. Season 1 doesn’t quite unearth buried treasure, but by the affecting finale, Our Flag Means Death charts its course in the right direction.
The first three episodes of Our Flag Means Death premiere Thursday, March 3rd on HBO Max, with further batches of episodes dropping weekly.
Annie Lyons is a culture writer from Austin, Texas who loves all things coming-of-age and romantic comedy. You can find her on Twitter @anniexlyons probably debating another Moonstruck rewatch.
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