The real Stede Bonnet’s time as a pirate was short-lived. After abandoning his wife and three children, along with a sizable estate and enviable fortune, the retired British army major took to the sea to live as a pirate in 1717. He was hanged for his crimes the next year.
Dubbed “the worst midlife crisis on record,” Bonnet’s brief second occupation still produced plenty of curiosities. In the 18 or so months spent robbing commercial ships, he also sailed alongside the feared pirate Blackbeard — and then sought to kill him. His upper-class background and poor sailing skills even earned Bonnet a nickname: The Gentleman Pirate.
Discovering such a striking character, out of place in a dangerous world, must’ve felt like finding gold for comedy writers David Jenkins (“People of Earth”) and Taika Waititi (“What We Do in the Shadows”), the creator and executive producer (respectively) of HBO Max’s “Our Flag Means Death,” which is loosely based on Bonnet’s life. Through five episodes, their farcical approach to Stede’s swashbuckling unearths plenty of treasure. Paired with a lively cast (led by Rhys Darby as the chipper Gentleman) and a handsome production fit for his vivid adventures, the new series is as silly and smart as we’ve come to expect from Waititi’s productions.
It’s also quite sweet, and one welcome surprise is the empathy elicited for Stede’s excursion. Rather than frame his pivot to piracy as a foolhardy endeavor embarked upon out of pure desperation (or, darker yet, a deep-seeded need to break bad), “Our Flag Means Death” paints The Gentleman Pirate as a dreamer, unwilling to settle for the life thrust upon him. The more common path these days would see Jenkins steering his ship into the murky waters between comedy and drama, where Steed might harbor a taste for violence rather than abhor it. Instead, by establishing an endearing lead, the comedy can lean into its absurd high jinks, bright, sun-shiny palette, and, you know, comedy. Even if his dicey aspirations walk him right off a plank, at least he’ll drown smiling.
That’s not to say the show will follow Stede’s tragic trajectory. Jenkins takes clear liberties throughout the first half of the season, even if he does check off many of the life events listed on Wiki. Picking up a few weeks after shoving off, “Our Flag Means Death” introduces Stede as an affable, oblivious leader. Dressed in frilly layers of spotless fashions, his well-coiffed hair barely swaying in the breeze, the captain of the Revenge is happy enough just to be out on the ocean. He doesn’t need to hunt down distant vessels or pillage lonely island towns. His ship (which he designed and purchased himself) is fully equipped with a rec center (where pirates learn tennis), a “jam room” (where the crew can beat on bongos or splay out in hammocks), and even a full library filled with books. (It’s later pointed out that shelves of heavy books on a swaying ship — next to an always-roaring fireplace — may have been a bad idea.)
Aaron Epstein / HBO Max
But his crew can’t read. They’re not musicians. And they aren’t too happy whiling the day away like Stede did when he was a posh fat-cat on land. They’re pirates — traditional pirates, who crave excitement beyond their (admittedly soothing) bedtime stories (read by Stede, with voices). “Our Flag Means Death” also points out these men come from the opposite end of the socioeconomic spectrum as Steed. They’ve had to fight and claw to survive all these years, and even though he’s paying them weekly wages (which never happens elsewhere), they don’t trust it will last. They can’t. Accustomed to surviving on the open seas by taking anything and everything that comes their way, the ship’s sailors are considering mutiny if Bonnet doesn’t lead them to riches.
His attempts to earn their respect result in run-ins with the English Royal navy, hypercritical aristocrats (played by Nick Kroll and Kristen Schaal), and even Blackbeard himself, embodied with a droll mix of swagger, inquisitiveness, and sequestered rage by Waititi. Revealed in teasing snippets, the legendary pirate earns his star turn not by inspiring terror, but through clever comedy and personal crisis. Blackbeard and Bonnet’s bond is fleshed out in ways indicative of great buddy comedies, yet always with an extra edge: If this odd couple doesn’t fit, only one will live to find another friend. Hearing Waititi and Darby bounce off each other — the former letting out surprising quips at a low growl as the latter responds with the buoyancy of Paddington Bear on a sugar high — is pure joy; two performers having magnificent fun with characters perfectly suited to their strengths.
“Our Flag Means Death” can’t always replicate the highs found when its top pirates cross paths. Episodes could stand to spend a bit longer within their strong comedic set-ups. Cast dynamics have yet to coalesce, though the supporting players — especially Samson Kayo, Joel Fry, and Vico Ortiz — establish distinct, enticing personalities. For an ensemble workplace comedy, the HBO Max original comes out of the gate with a confidence befitting a much more seasoned series. So unlike the real Steve Bonnet, here’s hoping this one gets a much longer time at sea.
“Our Flag Means Death” premieres Thursday, March 3, on HBO Max. The 10-episode first season will release three episodes initially, followed by three more March 10, and two each subsequent Thursday.