"It’s easy to look at HBO Max’s pirate comedy Our Flag Means Death and immediately type it as 'Taika Waititi’s latest project,'" says Tasha Robinson. "Waititi, director of Thor: Ragnarok, What We Do in the Shadows, and Hunt for the Wilderpeople, executive produced the show, co-stars in it, and directed the pilot. And that pilot in particular feels notably close to a version of What We Do In The Shadows, with pirates instead of vampires. The humor, built around a foppy, pretentious wannabe pirate captain and his crew of oddballs and misfits, falls directly in line with one of Waititi’s favorite themes: the mildly tragic, often hilarious conflict between the way people envision themselves, and the way everyone else sees them. Like virtually all his best humor, it’s wholly deadpan and utterly ridiculous at the same time. But ultimately, the series is more the vision of creator, showrunner, and writer David Jenkins. And after that setup, he takes the series in directions that people expecting a Waititi comedy might not expect — directions that make the show authentically memorable and admirable, instead of just the light, disposable sitcom fun that the first episodes tease. Waititi certainly isn’t a stranger to heartfelt beats or big drama, but the more the show builds throughout its 10-episode season, the more it comes from a completely different distinctive, specific voice. Which is why it might be a good idea to skip the premiere and wait a week before watching it, until enough of the series is available that you can binge it and get a better idea of what really makes the show worth the investment."
Our Flag Means Death is too droll for its own good: "Our Flag Means Death is always stuck feeling like it’s either trying too hard, or not trying enough; it plays out like the kind of comic experiment that must have been fun for its actors and filmmakers, while we struggle to get on board with its freewheeling dopiness," says Nick Allen. "It’s amusing in general to see the different cast members brought into the mix, mixing their different accents and comic sensibilities; it’s in the soft-spoken kindness of Samson Kayo’s Oluwande, the bizarre intensity of Ewen Bremner’s Buttons (sometimes with a bird on his head), the knife-throwing precision of Vico Ortiz’s silent Jim, getting to hear Nat Faxon riff on a Nordic account, etc. The various directors on this show then let them run amok with how they say their lines, and always keep them innocent and cartoonish. But while you can appreciate the creative energy of a self-amusing period piece like this, it only gives you some spare chuckles in return."
Our Flag Means Death arrives with echoes of several other series: "It’s a workplace comedy about a bumbling boss not entirely unlike The Office, but also a cheeky genre subversion like What We Do in the Shadows (with whom it shares an actor, pilot director and executive producer in Taika Waititi), with an earnest sunniness that could’ve been borrowed from Ted Lasso," says Angie Han. "But if Our Flag Means Death has a single defining quality, it’s 'cute' — and, yes, that’s a compliment. The core premise, of a series set during the Golden Age of Piracy but centering on a notoriously clueless pirate instead of a famously dashing one, is cute. The jokes that come from it are also cute, more geared toward chuckles than belly laughs."
Our Flag Means Death is racuously funny and surprisingly moving: "After a swath of serious pirate dramas and period pieces, Our Flag Means Death breathes salt-fresh air into the genre, with an unexpected approach to tackling the story of an aimless drifter who finds renewed purpose and expanded freedom by embracing a long-harbored dream," says Carly Lane. "In fact, there's a lot about the series that almost flies in the face of everything we tend to affiliate with pirates themselves but makes total and complete sense as it plays out on-screen. That's not to say that there isn't drama, that the stakes themselves aren't high, or that even death carries little weight, because the life of a pirate is a dangerous business. But ultimately, Our Flag Means Death is a show that exists in the same place as the sea itself: sometimes calm, sometimes raging, but never lacking in depth and surprises."
The 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," says Ben Travers. "It’s also quite sweet, and one welcome surprise is the empathy elicited for Stede’s excursion."
Rhys Darby and Taika Waititi enjoyed reteaming for Our Flag Means Death: "I feel really lucky when something like this comes along,” says Waititi. “This is the most fun I’ve had acting for a long time.” Darby, who has worked with Waititi on Flight of the Conchords and What We Do in the Shadows, adds: “I looked at myself and how much experience I’ve had over the years and I felt maybe it is time to step up. It was scary but having Taika there made it easier to do. We’re in this together and if he wasn’t there I’d probably track him down and call him to help me.”
Our Flag Means Death creator David Jenkins admits he wasn't a necessarily a big fan of pirate lore prior to working on the series: Really, it was the enigma of Stede that drew him in. “I think actual pirate stuff is fine, but it’s not necessarily my cup of tea. And I think Taika felt similarly," he says. "But hearing about this guy and reading about him and seeing that, you know, he left his family, then he met Blackbeard, they hit it off, and we don’t know any of the details in between. So filling those blanks in, and having a very human story, and then being able to do it with the pirate genre, that was like, ‘Oh, this would be cool.’”