REVIEW: ‘Our Flag Means Death’ Explores the Perks & Pitfalls of Piracy

Our Flag Means Death is an HBO Max Original series created by David Jenkins and based on the life of Stede Bonnet, the self-proclaimed “gentleman pirate.” Bonnet (Rhys Darby) attempts to escape a stifling marriage by gathering a crew of pirates and setting sail on the open seas. The only problem? He’s horribly inept at the piracy business, especially regarding the bloodshed and thievery inherent in the profession. Soon, Bonnet finds an unlikely friend in the form of the infamous pirate Blackbeard (Taika Waititi), who teaches him how to be a pirate in exchange for lessons in aristocracy. But Blackbeard may have his own agenda…

The series draws most of its comedy from the interactions between Bonnet and his crew, thanks to Darby’s offbeat charm. While most of his pirates are used to being ruthless killers, Bonnet encourages them to be polite and even take vacations when their ship runs ashore in the second episode, “A Dammed Man.” He even pays them a regular salary! His ship is even equipped with things you wouldn’t usually find on a pirate’s cruise, including a tennis court and a library (there’s a great running gag that features characters asking if the books will fall off the shelves).

Yet there’s more to Bonnet’s quest than the desire to be a pirate. Over time, his issues with his father and his struggles to be present for his family are revealed, making his shift to piracy feel like the world’s worst midlife crisis. And he soon learns the downside of piracy, as the pilot has him encountering one of his friends from his aristocratic life and accidentally killing him. It’s a shocking moment that serves as a reminder of how bloody and brutal a pirate’s life can be.

It’s also the biggest issue with the series; ever so often, a joke or gag will be followed up with something brutal, like a character suggesting a violent solution to a problem or a jar of alcohol fermented with severed noses. I don’t have a problem with black comedy—half of the fun of watching The Boys is how it portrays its superheroes as assholes. But comedy is all about timing and balance. You have to wait for the right moment to spring your joke, and the series never manages to find that balance throughout its 10-episode run.

It’s a shame because there are some great guest stars, and most of them happen to be great comedians! This includes Fred Armisen as a bartender on the Isle of Piracy (yes, that’s a location in this series), Leslie Jones as a ruthless pirate captain, and Kristen Schaal as a well-off socialite. However, the funniest moments of Our Flag Means Death belong to Bonnet’s crew, which include veteran pirate Black Pete (Matthew Maher), who speaks with a pronounced lisp, Buttons (Ewen Bremner), a man with a thick Scottish accent and an affinity for seagulls, the Bonfacia (Vico Ortiz), who disguises herself as a mute named “Jim,” and Oluwande (Samson Kayo), who offers Bonnet advice on pirating and attempts to keep Bonfacia’s identity secret while falling for her. It’s hilarious to see their reactions to Bonnet’s attempts at piracy and how often they save his bacon without him knowing it.

The standout of the cast has to be Waititi. While he’s no stranger to playing historical figures—see his turn as Adolf Hitler in Jojo Rabbit—Waititi delivers a more lowkey performance, infusing Blackbeard with a wily mind and a rockstar’s swagger. Seriously, I don’t think the real Blackbeard ever walked around in a leather jacket and fingerless gloves. It’s a far different energy from the performances that Waititi has brought to blockbuster fares like Free Guy and Thor: Ragnarok, but it’s a welcome one. The series reunites Waititi and Darby after their work on Flight of the Conchords. They have some of the best comedic chemistry I’ve ever seen and truly make the audience believe that these two wholly different people could forge a friendship. Waititi also directs the pilot, which sets the stage for the series.

Our Flag Means Death often struggles to balance its comedic and dramatic elements, but its ensemble cast serves as the highlight of the series. If you’ve loved Waititi’s previous work, especially the FX series Reservation Dogs, which he co-created, then this show will be right up your alley. And if it’s renewed for a second season, hopefully, it can manage to find a tone and stick to it when it comes to portraying the world of piracy.

The first three episodes of Our Flag Means Death are currently available to stream on HBO Max. New episodes premiere weekly on Thursdays.