One year ago this month, the long-awaited second season of Max’s hit pirate comedy Our Flag Means Death finally dropped. Which means we’ve now had a full year of getting to watch so many amazingly larger-than-life scenes over and over again. The tumultuous progression of Ed Teach and Stede Bonnet’s relationship, from their first reunion at Ed’s temporary deathbed to their final reunion on a beach full of murderous English soldiers. Ed and Stede’s fade-to-black sex scene, accompanied by Izzy Hands singing “La vie en rose.” MerStede appearing to Ed in a vision as Kate Bush croons “This Woman’s Work.” Izzy’s “It’s about belonging to something” speech, shortly before his untimely death. The entire gravy basket sequence. Stede committing his first intentional murder. Prince Ricky destroying the Republic of Pirates. Guest appearances by Minnie Driver, Rachel House, and Bronson Pinchot. Our cups really did runneth over last year, that’s for sure.
As much as I love all those huge season-defining moments, though, to me the heart and soul of this show is in its smaller, quieter moments. The moments that might not get mentioned in reviews or make it into trailers, but that change the characters’ lives (and, let’s be real, some of the audience’s lives, too) in smaller and subtler ways.
In honor of the one-year anniversary of Season Two, I asked myself something very important: Could I make a list my favorite moments like that, and then narrow it down from a very large number1 into something more befitting of… say, a listicle? A top ten, for instance?
No. The answer is no. But I did get it down to thirteen—a number that fits perfectly among the superstitions of “The Curse of the Seafaring Life,” one of my favorite episodes not just of the season, but of the whole show.
So let’s go! Here are my personal top ten thirteen quietly life-changing moments from Season Two of Our Flag Means Death.
13. Lucius’s Blackbeard Drawings
(Episode 5: “The Curse of the Seafaring Life”)
This show is at its best when it combines deep emotional insight with ludicrously over-the-top jokes. And I don’t think there’s a single gag that showcases this better than the drawings that Black Pete finds in Lucius’s sketchbook.
The fifth episode of Season Two sees Lucius trying, with mixed success, to process the trauma he experienced when Ed pushed him off the Revenge at the end of Season One. But try as he might, he can’t get Ed out of his head. Pete confronts Lucius about this when he finds a series of drawings that Lucius has done. A dog with Ed’s face. A pretty flower with Ed’s face. Pete’s own body with—you guessed it—Ed’s face. It’s an excellent shorthand for the way Ed continues to haunt Lucius, but it’s also just a fucking hilarious visual.
12. “And that’s another toe. Take your boot off.”
(Episode 1: “Impossible Birds”)
At the end of Season One, Ed memorably steals into Izzy’s quarters while he’s sleeping, then wakes him by cutting off his toe and forcing him to eat it. This functions both as punishment for Izzy threatening his life, and as a turning point for Ed’s character: the beginning of the dark, tormented, and suicidal months that many fans refer to as Ed’s “kraken era.”
The Toe Scene is horrifying. But by the time we meet these characters again in Season Two, it’s somehow gotten even worse. In this new era, toe-amputation-as-punishment is no longer new or surprising for Izzy. It’s something Ed’s put him through many times by now—a punishment Ed visits upon him whenever he steps out of line. It’s commonplace. It’s become routine, which, to me, is a far more potent horror than a one-off jumpscare.
11. Knife Parade
(Episode 5: “The Curse of the Seafaring Life”)
When Ed dons a sack and a bell and makes a public apology (more or less) to the crew of the Revenge for how he treated them, it’s pretty clear he doesn’t totally understand the full extent of what he did wrong. He might want desperately to be a better person, to leave his worst self in the past—but he’s still a product of the cutthroat world that shaped him, in which pirate captains hold the ultimate authority and never have to apologize for anything, let alone make amends.
Later in the episode, though, Ed tags along on his longtime crewmate Fang’s fishing excursion and reminisces about a game he used to play with his crew: “Knife Parade,” which seems to consist of, well, Ed chasing people around with knives. He remembers it being fun. He remembers Fang laughing as he ran away. But Fang gently recontextualizes things for him. Fang wasn’t laughing during this game; he was screaming. Fang wasn’t having fun; he was genuinely terrified.
It’s in this moment that true understanding begins to bloom: Ed’s mistreatment of his crew goes back years, and he’ll have to do more than making speeches about “moving the culture forward” to process that. Ed’s apology to Fang seems genuine—and I like to think that if the end of the season was a bit less rushed, we would have had time to see Ed making similarly genuine apologies to the others as well.
10. The Sea Goddess Calypso
(Episode 6: “Calypso’s Birthday”)
Everyone remembers Izzy’s unexpected and breathtaking appearance at this episode’s titular party, done up in glittery drag-inspired makeup and displaying a beautiful singing voice. But I’d like to give a shout-out to the queen who provided Izzy with all that makeup in the first place: Wee John Feeney, who reigns over the party in full drag, gown and all, as the goddess Calypso.
Kristian Nairn, who plays Wee John, has spoken in interviews about how drag (and, specifically, his character Revvlon) helped him find his voice as an actor, so it’s lovely to see a nod to that in Our Flag. And Nairn isn’t the only Our Flag actor with a background in drag; Vico Ortiz, who plays Jim, is also a drag performer, which likely inspired Jim appearing at Calypso’s party in that dashing mustache!
9. “Girl, how are you?”
(Episode 3: “The Innkeeper”)
Zheng Yi Sao, portrayed by Ruibo Qian, was an instant favorite among fans when she joined Our Flag for its second season. Brilliant, funny, and absolutely ruthless, Zheng has a relationship with Stede that’s rocky at best, evolving from allies to enemies and eventually back to allies again. But perhaps Zheng’s best moment with Stede comes in response to finding the ruined Revenge and learning what Ed has done to Stede’s crew. She’s genuinely asking how Stede is, and seems interested in the answer, making it a great moment of connection for them—but Qian’s stellar line delivery is what elevates it into the stratosphere. Like I said earlier: emotional insight + jokes = this show at its best.
8. “Works for spiders, works for men.”
(Episode 6: “Calypso’s Birthday”)
When Stede tells Ned Low to walk the plank following Low’s torture of Stede and his crew, Low seems baffled. Walk the plank and, what, jump into the water? Surely that’s not a thing! Low’s confusion is a playful nod to the (extremely unsubstantiated) rumors that the historical Bonnet may have been one of the few pirates to actually make his enemies walk the plank—and, indeed, may have even invented this particular form of punishment.
But when Low prompts Stede to explain himself, Stede’s response is this wonderfully inscrutable line. One can only assume that he’s made at least one spider walk the plank before trying it out on Low. As for why Stede might have made a spider walk the plank? Well, a few episodes earlier, we learned that Ed got spiders tattooed on his hands to help him get over his arachnophobia—which very much did not work. Apparently someone has to be the bug-killer in the relationship.
7. The Cake Toppers
(Episode 2: “Red Flags”)
In the first episode of Season Two, Ed and his crew raid a wedding ship. While the crew are killing people and stealing treasure, Ed plucks the groom figurine from atop the wedding cake and sneakily tucks it into his jacket. In the second episode, we learn that not only has he taken the bride figurine as well, he’s also painted a beard onto it so that it more closely resembles… well, himself.
The groom figurine, which already looks a whole lot like Stede, hasn’t been painted—but the smudge marks all over it suggest that Ed, his hands covered in the same kohl with which he now paints his face, has spent a lot of time holding it. In contrast with how he now treats the crew (not to mention himself), Ed’s treatment of these idyllic figurines is endlessly gentle. Ed’s a character who often externalizes his emotions, and in this moment we can see plainly what he’s been trying (badly) to hide from everyone around him: that despite the dark turn he’s taken, all he really wants is to hold Stede again, without violence.
The beard on the bride figurine has also sparked some very interesting debate, and inspired some wonderful fanworks, about Ed’s relationship to his own gender identity.
6. “He was either gonna watch the world burn or die trying. So which was it?”
(Episode 3: “The Innkeeper”)
When Ed’s kraken era began at the end of Season One, many fans theorized that Stede had no idea what he’d be getting into when he finally found Ed again. And when Stede and Izzy reconnect in the stabbed-up captain’s quarters of the poor Revenge, Izzy seems to assume the same thing. He hedges around what happened while Stede was gone; he tries to sugarcoat it, perhaps thinking Stede can’t handle it.
But Stede shuts that right down with these simple lines. We were all wrong; by the time Stede finds Ed again, he knows exactly what he’s getting into. His love for Ed isn’t contingent upon Ed never doing anything bad to anyone ever again. He sees Ed fully, and loves him unconditionally. It’s the kind of love that could maybe even, I dunno, bring someone back from the dead.
5. “There he is.”
(Episode 8: “Mermen”)
In the Season One finale, Izzy carefully delineates the difference between “Blackbeard” and “Ed”—one a ruthless legend that Izzy’s proud to work for, the other a “namby-pamby” who’s gone soft. When Ed responds violently to this, grabbing Izzy by the throat and pushing him against the nearest wall, Izzy seems beyond pleased. “There he is,” Izzy says of Ed’s Blackbeard persona.
Cut to the Season Two finale, in which Izzy apologizes to Ed for the part he played in bullying Ed into his kraken era. He admits that he knew Ed had long since outgrown Blackbeard, and gives Ed his blessing to just be himself from now on. As Ed weeps over him, Izzy uses one of his last breaths to echo “There he is”—only this time, it isn’t about Blackbeard. It’s about Ed.
I have a lot of issues with Izzy’s death, and I maintain that it didn’t need to happen. But this small parallel almost, almost made it worth it.
4. “Not on my life.”
(Episode 2: “Red Flags”)
Shortly after he catches them kissing in the hold, Ed orders Jim and Archie to fight each other to the death. It’s part of Ed’s suicide scheme—the one where he goads the crew into killing him so he won’t have to do it himself—but it’s also because, in his words, “All love dies. I’m just hastening the process.” (Remember what I said earlier about Ed externalizing his emotions?) Jim tries to refuse, but Archie punches them. The ensuing fight is bloody and brutal and a little bit sexy and extremely sad; it ends with Jim shoving Archie to the ground, whereupon Ed yells at them to finish the job.
We haven’t learned much about Archie by this point, as she’s new to both the ship and the show, but her response here gives us a vast insight into what her life must have been like before joining Blackbeard’s crew. Faced with imminent death, Archie says, “It’s okay. It’s just life,” essentially giving Jim permission to follow Ed’s order and kill her. Jim, though, refuses.
Throughout the first two episodes of Season Two, we see many scenes in which crew members try to care for each other through the horrifying days of Ed’s kraken era. But this is the first time we see anyone directly defying Ed’s orders—right in front of his face—in order to do so. When Jim pulls Archie to her feet instead of killing her, the tide begins to turn. The storm is still raging, and unnamed crew members are still being swept overboard—but as soon as Izzy shows up and stops Ed from destroying the whole ship, the crew, perhaps bolstered by Jim’s defiance, springs into action.
It’s also Jim who ultimately picks up a cannonball and, presumably, brings it down on Ed’s head, killing him. I’m obviously glad the death is only temporary and Ed gets a second chance—but I will always love Jim for standing up to Ed and doing what needed to be done.
3. Breakfast in Bed
(Episode 7: “Man on Fire”)
When I told my best friend I was putting this list together, her first response was, “You’re going to include the string on the breakfast tray, right?”
Obviously yes.
One crucial thing about Ed Teach and Stede Bonnet is this: relationship-wise, they have absolutely no idea what they’re doing. Before they met, Stede spent his entire adult life in a loveless heterosexual arranged marriage, while Ed spent his hiding behind a façade of leather and power and cruelty in order to survive. As much as they love each other, they don’t know how to be in an open, honest, loving relationship—but that sure won’t stop them from barreling ahead and giving it their all. And nothing reflects this dynamic better than Ed’s breakfast tray.
The morning after they have sex for the first time, Ed brings Stede breakfast in bed. It’s a distinctly unappealing affair, with various bits of unappetizing food arranged artlessly on a tray, featuring a small piece of twine as a flourish. When Stede asks him why the twine is there, Ed admits that he panicked—whereupon Stede assures him that it’s perfect. Pithy as it may sound, it really is the thought that counts here. Ed may not be very good at any of this yet, but he’s trying.
Plus, it’s just very, very funny.
2. “You just need to work on your mean voice.”
(Episode 5: “The Curse of the Seafaring Life”)
In the scene where Stede admits he hasn’t really felt much like a captain lately, and Ed gives him some pointers, Stede tries out his captain voice on Ed, telling him how he can be of more use around the ship. Ed only tells Stede to work on his “mean voice” because it’ll make his orders sound more authoritative. And he’s only wearing a bell around his neck at Black Pete’s suggestion; that part’s so he can’t sneak up on people.
But when you add those two things together, the full picture is so much more fun than the sum of its parts: Ed in a collar, telling Stede how to be better at giving him orders. Can you really blame the legions of fans who instantly assumed that Ed has an ulterior motive here? That Ed is hinting at what he wants out of a relationship with Stede? After all, we know Ed’s been tired for a long time of being Blackbeard—of always having to be the most powerful person in the room, of always having to take charge. So wouldn’t it stand to reason that he’d be very into someone else giving the orders once in a while?
1. “Fuck yeah, brother. Fly!”
(Episode 4: “Fun and Games”)
I would call Buttons turning into a seagull a season-defining moment. I would also call Izzy donning his unicorn leg a season-defining moment. But there’s a third character transformation that happens at the end of Season Two’s fourth episode—one that struck me as even more powerful than the first two.
When Buttons begins to perform the ritual that will turn him into a gull, Ed tells him to stop being weird. “People don’t change,” Ed says. “Not into birds or otherwise.” Button, heedless as usual to the opinions of others, continues the ritual—and becomes a seagull, flying (heh) in the face of Ed’s assumptions about Buttons, about people in general, and clearly about himself.
As Ed watches Seagull Buttons fly, we can see hope on his face for the first time all season. If this kind of mythical change is possible, maybe it’s also possible for Ed himself to change into someone who has a future again.
But hey, those are just my personal favorite moments from the second season. What are yours?
