Our Flag Means Death was the unexpected slow-burn sleeper hit of TV comedies in 2022, and now it is back with a second season that doubles down on all the things that garnered its passionately devoted fanbase—silly pirates, rom-coms, explorations of mental health, and unabashed queer love.
Picking up after Captain Ed “Blackbeard” Teach (Taika Waititi) stole the ship The Revenge from unlikely gentleman pirate Stede Bonnet (Rhys Darby) and marooned half his crew, season two of Flag finds the erstwhile piratical lovers separated and at odds. Ed is heartbroken and believes Stede betrayed him and is taking his misery out on his remaining crew, including Jim (Vico Ortiz), Fang (David Fane), superstitious Frenchie (Joel Fry), and possible sea witch/probable cannibal Buttons (Ewan Bremner). Also sailing with Ed is Izzy Hands (Con O’Neill), who is in every possible way worse off for his time with Ed.
Meanwhile, Stede is stuck in the Republic of Pirates with the marooned crew he rescued, including Black Pete (Matthew Maher), Wee John (Kristian Nairn), and Olu (Samson Kayo). They’re working for Spanish Jackie (Leslie Jones) and trying to figure out how to acquire a new ship. Stede writes love letters to Ed and stuffs them in bottles he heaves out to sea, while Olu has formed a slightly spicy friendship with a soup vendor on the island, Zheng (Ruibo Qian). They’re doing okay, especially compared to the Mad Max hell of The Revenge, where constant raiding and murdering has rendered the crew a traumatized, twitchy mess.
The first three episodes of Flag are darker than anything in season one, which was itself a Trojan horse for a melancholy story about broken men struggling to understand themselves in a world made hostile by toxic masculinity and their own mental health struggles. Taika Waititi, especially, hits some plumb but dark notes as Ed, sunk into self-loathing and depression. This is career-best work from Waititi as an actor as he easily slides between comedy and drama, particularly in the early going when Ed is at his lowest. Right alongside him is Con O’Neill, turning Izzy Hands from Ed’s cretinous first mate into a pathetic figure into a weirdly wise mentor for some of the crew. It says a lot about how dark things are on The Revenge that IZZY HANDS is talking sense.
After the first three episodes, though, things pick up as Ed and Stede, and their two halves of the crew, are inevitably reunited, but it’s not all smooth sailing. Ed and Stede struggle to find new ground, and relationships within the crew are tested by the volatility of their captains. Olu and Jim are reunited, but both formed new attachments in their time apart, and must figure out how to navigate their new realities while maintaining their own bond. And Stede and Ed encounter Anne Bonny (Minnie Driver) and Mary Read (Rachel House), ex-pirates not living their best lives ashore. No one has it easy in pirate life, and just as in the first season, Flag, for all its quirky humor and silliness, does not provide its characters with easy outs from their problems.
Stede and Ed still can’t fix each other, and sometimes, in the face of personal struggles, love isn’t enough. Ed’s self-loathing is almost overwhelming, enhanced by the feeling he drove Stede away, and Stede’s self-delusions edge himself and his crew ever closer to disaster. His ego, when fed the least bit of approval by other pirates, is immediately out of control and a direct threat to everyone else. Olu and Jim are the only remotely emotionally stable on that boat and absolutely no one listens to them. Izzy Hands, meanwhile, finds peace in reinvention, but that’s just one step away from repression, which doesn’t help anybody.
But Flag finds plenty of time for whimsy. An impromptu party leads to a drag show and Izzy singing beautiful, sad love songs—Con O’Neill got his start in musicals and Flag makes full use of this—Buttons is doing sea magic now, and the arrival of a pirate queen who “conquered China” means plenty of opportunity for plotting and back-stabbing and general piracy. There is also a new threat looming from Europe, in the form of a “minor prince” who runs afoul of Stede and Spanish Jackie. Stede and Ed are often in their own little bubble, but the world continues to move around them.
The second season of Our Flag Means Death celebrates what fans loved about the first season, particularly the multiple unapologetic queer love storylines, but also the terrific ensemble, the eccentric sense of humor, the fantastic fashion (costumes by Gypsy Taylor), and Mark Mothersbaugh’s jaunty sea shanty score. It does have a harder edge this time around, as the writers, led by series creator David Jenkins, commit to portraying Stede and Ed, and Izzy and most of the crew, as complicated people who aren’t always their best selves. It would have been easy to just lean into the “silly gay pirates” reputation of the show, but Flag continues to swim in deeper waters, balancing the humor with empathetic portrayals of mental health. For fans of the show, Our Flag Means Death’s second season is a welcome return to romance and intrigue and emotional breakdowns on the high seas.
This review was published during the SAG-AFTRA strike of 2023. The work being reviewed would not exist without the labor of actors. Our Flag Means Death season two is now streaming the first three episodes on Max, with new episodes streaming every Thursday.