Our Flag Means Death Creator David Jenkins Says Stede 'Becomes a Real Boy' in Season 2

[Warning: The following contains spoilers for the first three episodes of Season 2 of Our Flag Means Death.]

A dream sequence on a beach, a Kate Bush needle drop, and Rhys Darby with a mermaid tail can only mean one thing: Our Flag Means Death has returned. The swashbuckling romantic comedy series was a sleeper hit when its first season premiered in 2022, primarily thanks to the grounding love story between affluent gentleman pirate Stede Bonnet (Darby) and notorious bad boy Blackbeard (Taika Waititi, also an executive producer on the series), aka Ed — a sweet, tenderly awkward courtship between two guys who had never experienced romance before falling into each other's orbits… until Stede broke it off with Ed in the finale.

Season 2 begins dealing immediately and brutally with the fallout of that breakup, which affects the lives of everyone else in the series' sprawling ensemble. As Stede and the half of the Revenge crew he got in the divorce (which includes Samson Kayo's Oluwande and Matthew Maher's Black Pete) drift aimlessly in search of a way to make money, an untethered Ed has dealt with his heartbreak by reverting back to the savage, murderous persona that made him infamous. By the end of Episode 2, Ed's crew (including Joel Fry's Frenchie, Vico Ortiz's Jim, and Con O'Neill's poor Izzy Hands) violently strike back against the torture he's put them through. By Episode 3, Ed decides life is worth living if Stede is there to save him. (That's where the mermaid tail comes in.)

Creator David Jenkins, who directed and co-wrote the first two episodes of the season, caught up with TV Guide to break down the first three episodes of Season 2, discuss Stede's journey toward becoming a "real boy," and reveal what Olivia Rodrigo song he associates with Our Flag's central pirate couple.

You've spoken about how the response to Season 1 took you by surprise. Did having such a devoted, shipping-focused fandom develop around Stede and Ed affect how you thought about writing the show going into Season 2?
David Jenkins: If you're interested in the primary couple of a rom-com, is it shipping?

I think so. It's shipping.
Jenkins: I like it. It's the meat of the show, so it's great to have people bought into the central romance. If it were a bromance that we were trying to make look like a romance, that would suck. I think it would be terrible to write. To have them bought in on that is amazing, and it's amazing for us in the writers room. It's really gratifying. And I think for Taika and Rhys, it's really energizing for them that people love that relationship and they're invested.

Earlier today, just while I was scrolling my timeline, I saw a fancam for the two of them set to an Olivia Rodrigo song.
Jenkins: I love that. "You were my greatest crime." I tried to figure out a way to work ["Favorite Crime"] into the second season! I almost did it! "All the things we did just so I could make you mine." It writes itself. That, and Feist's "Let it Die" — that'd be a good end of Season 1 Blackbeard [song].

Do you make your own playlists for them?
Jenkins: I have very long playlists for each season, and then almost no songs make it in, because you can only use like, five songs. It really is the time that you have in an episode, and to really service a needle drop, you really need to give it the time and you need to pick your shots. If you're going to use Nina Simone, you really need to use Nina Simone. You don't just want to use five seconds of it and it's gone. It's hard to work that in for naturalism, you need something that has emotional size to be able to stick around in it.

Well, you brought up the Nina Simone needle drop. I want to get into that opening scene, the dream sequence. I'm curious about why you decided to open the season that way, and what went into shooting it.
Jenkins: I just like that it started with something badass. Stede, Blackbeard, and Izzy are on an arc together. Whether they're in stories together or not, their ultimate arc is together. I think, by the end of this season, the last episode, that first scene will be gratifying. I won't say why, but their fates are tied together. And then I like the idea that this season is about Stede becoming a real boy. He's still fantasizing about being a pirate, but his fantasies are much more about love, and fighting for love, but he's still trying to achieve that. He's not there yet. 

I also want to talk about that crew revolt against Blackbeard at the end of Episode 2. It's such a dark scene for this show.
Jenkins: He went too far. He's heartbroken, and he's also scary. But I think the thing that's good about this show is that it can go to really sweet comedy land, but I want there to be, like, if someone loses a body part, for instance, they lose a body part. To do justice to the fact that this guy is a killer and a monster, and dealing with heartache that he doesn't know how to deal with, I think you really need to go there. It can't be a comedy version of it. It needs to be a real heartache for him, because it gives him something to come back from.

What do you imagine was going through his mind in that moment? He says, "Finally," which is so chilling. 
Jenkins: Yeah, he wants to get the crew to kill him. When Izzy maybe kills himself in the middle of the episode, [Blackbeard] knows what he's going to do, he's decided early on that he wants to die, and he's lost all hope, and kind of become the monster that everyone said he was, but he never really was. And then the thing that I like about that episode is Vico's performance in it, and I love that Jim has become the one who carries on what Stede taught them. They say, "Life used to mean something on this ship." And then at the end of the first episode, they tell Fang the story of the wooden boy. They're kind of carrying the torch of what Stede started on that ship, and they were the most resistant to what Stede was doing in the first season. 

It was really sweet watching the crew care for Izzy, who's really going through it this season, and I thought it was so interesting for him to be the one to stop Blackbeard from destroying everything. What did you want to accomplish with Izzy's journey this season?
Jenkins: He's such a good character. To see him as more than just a villain and a downward pressure and someone to get them into trouble… I mean, he's jilted. He had a partnership with Blackbeard, and he knows he can't live up to this person that Blackbeard fell in love with. To watch him come full circle, and kind of go in a bit of a Lieutenant Dan storyline this season where he's lost everything, and then what? Who is that guy? What are his hobbies? What does it look like when he's not totally subsumed with his boss's love affair with somebody, and heartbroken? I love Con as an actor and I love what he brings to that role. I think it was really just to have a full meal for Izzy in this season.

To keep talking about those arcs, I kept thinking about the end of Episode 3, when Blackbeard dies and then comes back. It felt very Tony Soprano.
Jenkins: We talked about The Sopranos dream sequences a lot. [Writer] Eliza Jiménez Cossio is a big Sopranos fan.

And he and Stede come back together at the end of that dream sequence. How did you decide to reunite them so early in the season? You don't drag it out.
Jenkins: I think it would suck to have to sit through a season and then have to invent all these reasons they don't meet up. The show is them navigating each other. That's the meat of the show. The first season is them realizing they have these feelings, and trying to figure out what to do with them. The second season is them being a little bit more mature and figuring out, "What do we do? Now that we've had these feelings, we've broken up, we've gotten back together." What does it mean to be in a relationship with somebody that you have these feelings [for]? It's the thing where you're in your 20s or 30s and you're like, "Well, should we move in together?" They have to make up some time because neither of them have been in a functional relationship before.

There are also a bunch of new characters this season. What was important to you about integrating them into the mix with the rest of the ensemble?
Jenkins: I think the big thing is just making sure everyone has enough to do, and that the new characters that come in just feel like a part of the world and it feels like a big cohesive world. They're bringing some scope to it. But also, I think the big thing with adding characters to the show is like, what do they want? And their wants are pretty modern. Their wants are usually relationship wants. This show is maybe more to do with Insecure and maybe Grey's Anatomy. [Insecure] is a show about multiple relationships. That's what I want to see when I see this show. I don't want to see a bunch of pirate things that I've seen in other things, I'll just go watch another thing if I want to see that. That's not really my thing. I like the genre, but it's a very hard genre to budge. I want to see relationships in a pirate world. To me, that's what was good about The Princess Bride. There's a lot of really well drawn characters in a fantasy world, but we don't need to see dragons and giant CGI explosions and stuff. That's a relationship [story]. That's what I want to see. That's what I'm interested in.

You brought up Insecure, you brought up The Princess Bride. You also said that your big inspirations during Season 1 were A Star Is Born and John Hughes movies. What were some of your other inspirations going into this season?
Jenkins: Well, I love A Star Is Born and I love the Bradley Cooper Star Is Born. I think it's really good, man. I like it earnestly and then I like it on a kitsch level. I like how earnest it is. I'm invested in the relationship, and I think to watch Stede — spoiler, but he becomes a real boy, and he becomes a notorious pirate. To see Ed try to process that, Ed's more like Jackson Maine, and then Stede's doing a Gaga, and he's blowing up. There are some feelings about that. So we talked about that in the room.

Without giving too much away, is there a particular episode you're most excited for fans to see?
Jenkins: I'm excited about so much of it. I'm really excited for people to see mermaid Stede. I want to see some Rhys Darby mermaid tattoos. He looked beautiful. He was in the tail, he knew he looked good.

The second season of Our Flag Means Death streams Thursdays on Max.