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.