Review: ‘Our Flag Means Death’ Delivers an Entertaining, Contemporary Presentation of Piracy’s Golden Age

The best only seems to be ahead for Taika Waititi, the executive producer, director, and co-star on the new HBO Max series, Our Flag Means Death.

Just when he seems to have delivered his best work, he’ll come out with something every bit as clever, entertaining, and engaging as anything the director’s done in the past, as is the case with this satirical, contemporary swashbuckling comedy.

Our Flag Means Death stars thoroughly underrated New Zealand actor and frequent Waititi collaborator Rhys Darby as Stede Bonnet, a real-life historical pirate who abandoned his comfortable, lavish life in upper-class society to sail the high seas as a buccaneer.

Donning the moniker, “The Gentleman Pirate,” Darby’s fictionalized Bonnet tries to establish himself as a fearsome pirate in the Caribbean during the early 1700s’, only to be constantly thwarted by his inexperience, kind nature, and distaste for violence, much to the frustration of his grizzled, practically-always-to-ready-mutiny crew.

Despite being based on the historical Bonnet, Our Flags Mean Death is far from a period piece, bringing a sharp, off-beat, contemporary portrayal of life in the 18th century that more closely resembles Monty Python than it does Pirates of the Caribbean or Black Sails.

Much of the comedy comes from Bonnet’s ridiculous desire to be a feared pirate, even though he clearly isn’t up to the task. Not only does he possess a foppish, incredibly out-of-place physical appearance (paisley vests, elegant jackets and shirts, and so on) that horrendously clashes with his crew’s more rugged, slovenly appearances—Stede is simply too nice to be a pirate. He lacks the ruthless, violent tactical mind to wreak havoc, is completely against any form of violence, and is utterly inexperienced when it comes to basic pirate responsibilities, such as sailing or swordplay.

Bonnet’s decision to become a pirate in the first place provides much of the overall comedy and drama of Our Flag Means Death’s first three episodes. Bonnet may be portrayed as someone who’s comically out of his element, and whose appearance, attitude, and personality clash with the more down-and-dirty pirate lifestyle, but the show’s exploration of his past provides a surprisingly emotional nuance to his character.

As seen through intermittent flashbacks, Bonnet grew up extremely wealthy not because he earned it, but because he sort of lucked into it—something his overbearing father callously reminded him of when he was a young boy.

Throughout his life, Bonnet was routinely bullied or ignored by everyone around him—schoolmates, his father, even his own wife and children. As a result, he failed to form any genuine social or emotional connections of any kind, leaving him with a feeling of severe sense of inadequacy and loneliness.

Our Flag Means Death
Courtesy of HBO Max

Desiring to make something of himself, Bonnet leaves—to find adventure, yes, but also searching for the sense of connection he never received in his old life. “My family's here now,” Bonnet tells himself when his ship, The Revenge, sails off at the end of the pilot.

It’s Bonnet’s inner emotions that make the series so entertaining and watchable—his doubts, insecurities, uncertainties, even his guilt about leaving his family prevented him from becoming just another cliched, airheaded protagonist that we’ve seen countless times before. Luckily, too, the emotion never feels forced—mainly because of how much disdain Bonnet’s crew holds for him. (As Stede prepares to be executed at the end of episode 3, Jimenez—one of Bonnet’s crew—tells him blithely, “You are the worst f*cking pirate captain in history” as a farewell message.)

Aside from Darby—who is, as always, fantastic to see in any role—the other actors on the series also shine bright. Included in Bonnet’s crew are a wide range of underrated comic and dramatic actors, such as Game of Thrones alum, Kristian Nairn, as Wee John Feeney, a pyromaniac with a love for children’s stories and sewing; Ewen Bremner as the slightly cannibalistic helmsman, Mr. Buttons; and Matthew Maher as Black Pete, a frequent critic of Bonnet’s who claims to be former crewmates and best friends with Blackbeard (even though Bonnet is the only who believes his wildly exaggerated stories).

Particular members of the crew that the show focuses on are Samson Kayo’s Oluwande and his companion, Vico Ortiz’s Jimenez—a pirate who is secretly a woman, hiding behind a false nose and large beard, and who is currently on the run for killing a powerful pirate’s husband. Though Jimenez sees their relationship as strictly platonic, Oluwande is revealed to harbor romantic feelings towards his crew member.

An interesting B-story that the show’s been focusing on more and more with each new episode, it’ll be interesting to see where exactly the storyline with the two crewmates will turn to next. In the most recent episode, they shared an incredibly suspenseful encounter with their old adversary, Spanish Jackie (Leslie Jones) and her other husband (Fred Armisen). Additionally, Jimenez's secret identity as a woman was also made public knowledge to the rest of the crew. Likely, the main plotline for their story will revolve around whether Oluwande will admit his feelings for Jimenez, but in the meantime, it’s also worth pondering how exactly Jackie and her 18 other husbands will figure into the remainder of the season.

However talented the main cast of the show is, the various guest stars and supporting actors that have appeared on Our Flag Means Death are also a frequently enjoyable aspect of the series.

Jones and Armisen hand in some incredibly fun performances as the seedy antagonists at the Republic of Pirates—Jones playing the no-nonsense Spanish Jackie and Armisen as her barman husband. Rory Kinnear is unbelievably funny as the arrogant, memorably-named Captain Badminton, an officer of the Royal Navy and childhood bully of Stede’s. (Aside from Armisen peeling off Jimenez’s false nose in episode 3—much to the horror of the screaming crewmen—the hardest I personally laughed was seeing the elegant-looking Kinnear in a period-accurate naval uniform furiously flipping off Bonnet.)

our flag means death fred armisen leslie jones hbo
Courtesy of HBO Max

According to announcements regarding the cast listing for the series, other notable actors that will play recurring roles in the show will be Nick Kroll and Kristen Schaal. Both have yet to make an appearance on the show yet, but are certainly welcome additions to the show’s already-impressive cast listing.

Our Flag Means Death may have been created by David Jenkins, the man behind TBS’s People of Earth, but it seems like the kind of project Waititi is known for: a comedic subversion that presents the Golden Age of Piracy in an hilariously satirized manner, not at all dissimilar to Waititi’s exploration of vampires in What We Do in the Shadows.

It’s easy to see what attracted Waititi to Jenkins’ series, and really, it’s a show that’s tailored to Waititi’s strengths and comedic style (we’ve yet to see much of Waititi’s Blackbeard, but what we’ve seen has been very promising so far), making it the perfect show for fans of the New Zealand director.

With Blackbeard having made his memorable introduction in episode three of Our Flag Means Death, it’ll be fascinating to see what his initial interactions with Darby’s Bonnet will be like in the next episode, scheduled for release this Thursday, March 10, only on HBO Max.

Our Flag Means Death is streaming now on HBO Max.

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This post was produced and syndicated by Wealth of Geeks.

Image Credit: HBO Max.

Richard Chachowski is a freelance writer based in New Jersey. He loves reading, his dog Tootsie, and pretty much every movie to ever exist (especially Star Wars).