In Season Two, ‘Our Flag Means Death’ Keeps Beautifully Mixing the Present into the Past

WARNING: Contains spoilers for Our Flag Means Death (mostly regarding Season One). 

Intentional anachronism in a period comedy is, to understate things, a mixed bag. Done well, you get acclaimed goofs like Another Period and Dickinson. Done poorly, and you end up on a list of legendary bombs alongside Year One and Your Highness. For its first season last year, Our Flag Means Death was squarely in the former category; miraculously, the second manages to surpass it.

In the first season, we meet Stede Bonnet (Rhys Darby), the Gentleman Pirate. Bonnet was a real person, and the appellation (or affectation) aligns with the historical record. But as portrayed in the show, Stede goes past gentlemanly with the disparate misfits in his crew. The series premiere closes with him tenderly reading them all a bedtime story. Piracy is a pursuit in which toxically masculine traits tend to be rewarded (including among women, such as Leslie Jones’ fantastic Spanish Jackie), but Stede feels that it doesn’t have to be that way: One can enjoy a life of adventure on the high seas without hoarding wealth — he pays his crew fair wages — or demeaning anyone. The first few episodes seem like the clash of Stede’s contemporary management style and the prevailing mores of 17th century piracy is going to be the show’s main gag. Then, in Episode Three, we meet Ed/Blackbeard (Taika Waititi, also an executive producer). Over the next several episodes, the show changes into a delicate love story between the seasoned plunderer and Stede, the relative pacifist.

Even in a selectively anachronistic context, a culture of violence, bigotry and compulsory heterosexuality can’t be completely overhauled by one or two visionaries; some regrettable decisions, and some bad luck, toward the end of the first season play out in the second. Stede and some of his former crew end up in the Republic of Pirates, destitute enough to throw themselves on Spanish Jackie’s mercy for shelter and front-of-house jobs in her bar. Having renounced his familial wealth hasn’t made Stede any more canny about money, and his remaining compatriots hate telling him that he’s never going to save enough to buy a new ship out of the pittance Jackie is paying everyone. 

Meanwhile, the rest of Stede’s old crew is still on his old ship, the Revenge, now captained by Blackbeard — and Blackbeard’s not doing well. All he knows for sure is that while he was waiting for Stede to join him in fleeing their current lives and lighting off to China, Stede returned to his estranged wife Mary (Claudia O’Doherty) and their children in Barbados. Blackbeard doesn’t know Mary and her new lover Doug (Tim Heidecker) helped Stede fake his death to escape criminal prosecution so that Stede could reunite with Blackbeard. So in an extremely unfortunate misunderstanding (you know how many Seinfeld plots would be instantly resolved if the characters could text? It’s like that, but with a lot more grisly deckside murders), Blackbeard is taking out his heartbreak on every other ship in his vicinity. 

Even the crew think the raid on a civilian wedding at sea was over the line, and what’s the point when Blackbeard is so depressed that he just wants to dump all their plunder overboard? Trade routes being what they are, the two exes can’t, of course, be kept apart forever, but the specific circumstances of their reunion are delightfully unexpected, as is nearly everything that follows.

Though Waititi wears multiple hats on Flag, he did not create it. Sometime playwright David Jenkins did, in only his second TV credit after TBS’ sadly short-lived alien sitcom People of Earth. The early bad buzz around Waititi’s next film, Next Goal Wins — for its transphobic portrayal of Jaiyah Saelua, a real-life fa’afafine (third gender) athlete who played on the American Samoa soccer team documented in the film — should make it clearer than ever that Jenkins, not his EP, is the creative force behind the show’s many three-dimensional queer relationships. (In an interview with Steven Prusakowski at AwardsRadar last year, Jenkins elaborated on his determination to portray the queer experience without letting characters’ trauma drive the plot.) 

Nonbinary Jim (Vico Ortiz) grows closer to new Revenge crew member Archie (Madeleine Sami). When Jim and their Season One crush Oluwande (Samson Kayo) cross paths again, they gracefully slide into platonic friendship. Without spoiling it, one of the season’s most hilarious character introductions comes midseason when Blackbeard chances upon an old acquaintance and her female partner. What reads to outsiders as potentially murderous hostility is, apparently, just how these two keep things fresh after years of living together. This couple’s lusty violence — do you really love your partner if your foreplay has never incorporated a non-fatal stabbing? — is a bracing contrast to Stede and Blackbeard’s shy and tentative fumblings. Another queer couple misses a raid on the Revenge because they’re in the hold carnally celebrating their engagement. A party late in the season is enlivened by some absolutely gorgeous drag performances. And since none of its queer performances read like mere tokenism, it’s easier to celebrate straight couples, too — although Jackie adding a new husband to the nearly two dozen she’s already assembled does also feel kind of queer in its way.

Even more so than in the first season, the show’s most impressive feat is that it actually makes room for everyone in its very large cast. To name just a few examples: A new secondary character identifies Buttons (Ewen Bremner) as a sea witch, and gifts him a spell for avian transmogrification that the noted seagull communicator finds very useful. Blackbeard’s former first mate Izzy (Con O’Neill) pushes the boundaries of contemporary standards in both prosthetics and emotional intelligence. Cook/doctor Roach (Samba Schutte) creates a now-ubiquitous spread more than a century before its official invention. And unassuming Fang (David Fane) gets several showcases to share his wisdom and discloses his real name. Not to give the acting and writing short shrift in making each of 14-plus characters feel like distinct individuals, but the costuming and styling also help, the latter having been very correctly recognized with a prize earlier this year at the Hollywood Makeup Artist and Hair Stylist Guild awards.

By the end of the seven (of eight) episodes provided to critics, you may wonder along with one of the characters how Stede — famously humane on top of relatively unskilled — has survived as long as he has, particularly in combat against opponents with much more training, experience and bloodlust. (Since it’s established this season that magic is real: If an ineffable power is supernaturally protective of Stede, I, for one, would accept that.) On the other hand, we can all come up with real examples of untalented people failing upward, through chance or with the boost of powerful associates. Stede may be undeserving of being where he is, but unlike most beneficiaries in his position, at least he’s nice! 

And if one of the jokes of Our Flag Means Death is that Stede and his ethos are ahead of his time, maybe the real joke is how far the show is ahead of ours.