Max’s pirate comedy “Our Flag Means Death” felt like a pretty standard spoof of pirate pop culture when it started its first season, but it developed over that 10-episode run into something much richer, smarter, and even moving by its end. As it navigates the tricky waters of streaming comedy in the 2020s, David Jenkins’ show has found a very loyal fan base; one attracted to both its smart sense of humor and its notable representation of LGBTQ+ characters. The second season feels lighter at first until it becomes clear that it’s really grounding the main theme of this show: finding yourself, sometimes, in the most unexpected places. This is a program about people who have been labeled—the gentleman and the pirate, for example—and how the real freedom of the open seas in this world is when those labels get shed for personal growth. It’s a funnier season than the first, with some great guest appearances and an intelligent level of growth in the ensemble, allowing a stellar supporting cast time to develop this increasingly lovable crew.
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“Our Flag Means Death” is very loosely based on the true story of Stede Bonnet (Rhys Darby), known as the “Gentleman Pirate,” a wealthy landowner who decided to leave it all behind and sail the seven seas in the late 17th century. Jenkins and his team of writers imagine Bonnet and his ragtag crew aboard the Revenge crossing paths with the infamous Blackbeard (Taika Waititi). While these two seem as drastically different as a pair of ocean travelers could be, they formed a loving relationship in the first season, one that led to Stede finding a bit more courage and Blackbeard (aka Ed) finding a bit more of his heart. While their dynamic was the center of the first year, the writers also deftly built out some supporting characters, planting seeds that find notable room for growth in the sophomore outing.
The first season of “Our Flag Means Death” ended with its best episode after Stede decided to go home, leaving pirate life behind when he learned that his wife Mary had declared him dead. Leaving a heartbroken Ed behind, Stede realized that he couldn’t just live a normal domestic life—the freedom he found as a pirate with Ed was where he belonged (and Mary kind of wanted him dead anyway). They hysterically collaborated to fake his death while Ed sunk deeper into his vicious Blackbeard persona. He became more violent, lashing out at the crew before stranding most of the survivors on a deserted island. The season ended with Stede finding a few of his mates but separated from his true partner.
The opening arc of season two of “Our Flag Mean Death” contrasts how two men would respond to being devastated by separation. Blackbeard becomes the dark version of himself, a vision of someone who just wants to see the world burn if he can’t be happy in it. Stede becomes the optimist, convinced he can somehow find a singular man on the open seas despite logic making that pretty unlikely. The first three episodes of the year are phenomenal, allowing Darby to play an emotional undercurrent of hope that his wide-eyed optimism has always done well and allowing Waititi to lean into the legend of a ruthless pirate in a way that’s both fun and even a little moving. Cruel pirates are a common part of pop culture, but it’s rare to see one who also produces sympathy because of how Waititi intertwines the bad behavior with honest heartbreak. And, without spoiling, the writers keep Darby and Waititi apart just long enough, knowing that the show works best when these old friends are allowed to display their comic chemistry together.
As great as the throughline about Ed & Stede through the seven episodes sent to press are this season, the year wouldn’t be as notable without the consistent growth of the entire ensemble. Comedies often take time to find ways to play to all of the strengths of their cast, and “Our Flag Means Death” is really doing that in season two. Standouts include Con O’Neill as the stubborn Izzy, Matthew Maher as the lovable Black Pete, Joel Fry as the reliable Frenchie, and Samson Kayo as the charming Oluwande, who gets a great arc this season with another pirate that won’t be spoiled. Some of the guest stars from season one also return, along with a few excellent new ones that won’t be spoiled. Much of the joy of “Our Flag Means Death” comes from seeing the unexpected places these characters go in each episode and who they find there.
What makes the second season of “Our Flag Means Death” special is how much the writing leans into both a greater degree of representation and a consistent theme across all of its subplots about fighting back against societal expectations. Even guest arcs this season seem to fit into this idea from Jenkins and his team that people can only really find happiness when they escape the box in which society has placed them. Everyone brings their baggage onto these ships; it takes good mates and even a partner to throw it overboard. It may not be a good idea to leave everything behind and become a pirate in 2023, but everyone can relate to a show that’s fundamentally about people figuring out how to be happy. [A-]