Editor’s note: The below interview contains spoilers for Our Flag Means Death Season 2.

It’s hard to wrap our heads around the fact that Max’s Our Flag Means Death has already reached its Season 2 finale — serving as proof that life for pirates can be just as tumultuous and unpredictable on land as it is on the open sea. Although Stede (Rhys Darby) and Ed (Taika Waititi) saw themselves reuniting in epically romantic fashion on a beach (before having to jump in and help Zheng [Ruibo Qian] swordfight a bunch of foes, that is), their plan to reassemble the crew of the Revenge and take back control of the Republic of Pirates didn’t come without some losses. Namely, Ed’s first mate and loyal right-hand man — and newly-dubbed unicorn of the crew, Izzy Hands (Con O’Neill) — fell to a gunshot wound, but didn’t slip away without some important parting words that Ed himself needed to hear.

Now, the future of the crew is looking divided once more — but on a somewhat happier note this time around, as Stede and Ed are settling down in that innkeeper life while watching the Revenge sail off into the sunset under the command of Frenchie (Joel Fry), and all set to the tune of Nina Simone’s swelling and ultimately hopeful cover of “The Times They Are a-Changin’.” It’s unclear where the show will go next, but ahead of the finale, Collider had the chance to sit down with Our Flag Means Death music supervisor Maggie Phillips to break down some of the best needle drops, from O’Neill’s cover of “La vie en rose” to making Kate Bush the unexpected artist of Season 2 to collaborating with show creator David Jenkins and so much more.

Our Flag Means Death Release Date March 3, 2022 Cast Rhys Darby, Taika Waititi, Rory Kinnear, Con O’Neill Main Genre Adventure Genres Comedy, Action, Adventure, Biography Rating TV-MA Seasons 2
COLLIDER: Before getting into some specific episode moments, I wanted to ask you about the teaser trailer for Season 2. Something that a lot of people were talking about was that Prince song that gets used [“The Beautiful Ones”]. Did you all get to decide what song that was in the trailer?

MAGGIE PHILLIPS: We did. That was a song that David [Jenkins] asked me about. I don’t know if he asked me about Prince or that song in particular, but that’s the first song that David and I were like, “This is the song for the show,” before trailers were even thought about. We tried to get it into Season 1, and there just wasn’t a spot for it. I’m a huge Prince fan and have been since high school. For Halloween, when I was 17, I dressed up as a B-side Prince song. It was a song called “Scarlet Pussy.” It was a red cat. [Laughs]

Prince has been kind of off-limits for my whole career. Prior to his death, he was very picky and very expensive, and it was just something I was never really able to place. Then, when David brought it up, it was like two-and-a-half years ago, his estate was still being settled in court, and I was like, “I don’t know if we can use it,” and then we were trying to use it, and it didn’t work out. Long story short, we tried again to place it in Season 2, and there just wasn’t a spot for it. So then, when we were doing the trailers, I don’t normally get consulted for those, but David asked me to watch it and asked my opinion. Since then, Prince’s estate had been settled, and I had heard that, actually, his estate wanted to place his music. It was perfect, and I’m glad that the first time I placed a Prince song was for Our Flag Means Death. That was a song we’re very happy about.

Have there been any big instances where a song doesn’t fit somewhere in the season, you can’t find a place for it, or where you’ve tried to get your first choice for this show specifically, and it hasn’t been able to happen for whatever reason?

PHILLIPS: No, none that come to mind. I don’t think we’ve had any denials. The big moments in Season 1 we cleared before they even started shooting. Cat Stevens and the Fleetwood Mac were costly, and that meant cutting corners elsewhere, but we got everything we wanted. We weren’t shooting for the stars that much. At this point, in Season 2, it’s been easier to get yeses, I will say that. Kate Bush in Episode 3, her manager was very specific. Kate wanted to be a part of it, and she was very excited about the use and stuff. The show is so popular, with enough of an audience that people want to be a part of it, which is very exciting.

Image via Max

When I talked to David before the season, he said that he always picks a song and that’s the song that’s all-encompassing of the whole season. For this season, he said Kate Bush, “This Woman’s Work.” Obviously, we get it in a very pivotal moment in Episode 3. I wanted to ask you about the conversations around that song and when it was going to be used.

PHILLIPS: It recontextualizes the song and the lyrics to make it work with that scene. That song was written for a movie, She’s Having a Baby, with a totally different subject and lyrical subject in mind. The funny story about that song is I advised against it when he told me he wanted to use it. There were two reasons: the more egotistical reason was I had placed it in The Handmaid’s Tale previously, and I hadn’t actually pitched that song. I had pitched “Running Up That Hill” for that episode, but the showrunner decided to use “This Woman’s Work,” and I was like, “That’s a bold choice. Some people are going to love it, some people are going to hate it.”

More importantly, it was right after the Stranger Things Kate Bush phenomenon, and I was like, “Dude, we are going to look like we are copycats, that we didn’t have an original idea, and I’m worried about the backlash there.” David knows what he wants, and he was like, “This is our show. It’s an original, and this is the right song for this moment.” Taika wanted to use the song and was very attached to the song, too. So it was a Taika/David collaboration, that song.

I remember talking to my team and saying that this could be potentially embarrassing, this song in this spot, but then, I watched it. I read the script. I’m not privy to the conversations about how they’re gonna shoot it and what part of the song they’re gonna use, but they had obviously figured that all out — because I watched it and really was emotionally charged. I remember getting chills, and I emailed David right away, and I was like, “You were so right. That song is gorgeous there.” I feel like it changes the song. It becomes a new creative moment. That’s what’s so cool about this job. It’s rare, but sometimes you’ll put a song to picture, and the song will change, and the picture will change, and it’s sort of that movie magic, and I feel like they did it there. So I just was along for the ride and got to eat my words.

Speaking of a music moment that gave me chills, Episode 2, that Timber Timbre song, “Run for Me,” bookends the episode and is used in very different contexts with very different parts of the song. At the beginning, it’s Blackbeard wallowing and depressed, and at the end, it’s this very sinister, dark place. What was the process behind choosing that song and also choosing to use it in two very different places?

PHILLIPS: That was all David. I wish I could claim that that was me. I read it in the script. I’m a fan of Timber Timbre; I put them in stuff years ago. I’ve followed their career since they started, so I knew the song immediately and read the script with that song in mind. No, [that was] just the genius of David Jenkins.

Image via Max

How often are you getting scripts from [David] where the song choice is already in there?

PHILLIPS: It’s rare, because typically he asks me before he writes a script. Typically, he’ll email me while he’s in the writers’ room. In fact, I’m sure he did about this one because it was so intricately woven into the script, and he’s not going to write it without knowing that we can clear it and can afford it. Since I know Timber Timbre, I’ve used their stuff before, I was like, “Go for it. It’ll be affordable and easy to clear.” In that regard, he might have asked me for some [other] stuff, and I’m like, “Stay clear.” Those might be the only denials we’ve gotten, from me, but there aren’t many these days. There used to be a lot more that were hands-off. These days, people want to be seen.

I also love the use of “Strawberry Letter 23” during the raid on the wedding in the first episode. It’s juxtaposed against the violence and the terror of the moment.

PHILLIPS: It’s such a sweet love song. The lyrics are so innocent and sweet, but it’s like the way that Shuggie Otis — it’s swagger and cocky and just whimsical and has that strong melody and the instrumentation. That was on one of my playlists for Season 1, and then [David] wrote it in. All the big moments in Season 1 and Season 2 that are on cameras like that, those don’t come in post. Those are when he’s writing the scripts, so there was never any other song that was attempted for that spot; that was always going to be that song.

With that in mind, what’s the song at the end of that episode, where Ed and Stede are both looking at the same moon and having their respective conversations?

PHILLIPS: It’s “Pygmy Love Song” by Francis Bebey. It’s supposed to capture the pain but inherent beauty of true love. It’s romantic but tragic at the same time, like Stede and Ed’s love story —at this point in the story.

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I also wanted to about Con [O’Neill] singing “La Vie en rose” in Episode 6. I feel like that’s a moment that fans are going to be really excited about. I personally did not know he could sing!

PHILLIPS: I don’t know if he knew he could sing either. That was a very involved clearance. It took a long time to clear. Anything that’s international, and this was through the French office, takes a long time. Americans are very quick, for better or for worse, and the French office is not. We started clearing that, and it took us months. We were getting to the point where we were like, “Are we gonna be able to use this?”

Then Con was anxious about singing in the first place because it’s not something he does normally, and then was anxious about singing in French. So we had to change the clearance because originally scripted, we wanted it to be in French, and going back to English, that actually was a whole other boring clearance story. To get it approved in English was harder, but we got it. Then, while we were waiting for approval, the actor had taught himself phonetically how to do the French version, and we recorded both options, and the French was so effective that that’s what we stuck with for most of it.

I love that moment. [Con]’s such a good actor. Oh my god. That episode is just really powerful, and that song works really well Sometimes when you’re not a trained singer, but you’re an actor, you’re acting the singing as opposed to singing it for the aural experience, so it becomes more emotional in a way. You’re not worried too much about pitch and getting it right, and so it’s more about the character who’s singing it. Especially when you’re singing it not for a soundtrack but in a scene. They’re not singing it for the performance, they’re singing it for the cathartic release, and it is going to be more emotional. That’s why I think it’s so powerful, the way he does it. Yeah, I love that scene.

Do you have a personal favorite song choice from Season 1?

PHILLIPS: My favorite, because I love the way it works, and it’s also just for me a personal triumph, [was] to get Moondog in at the end of the pilot. It was such an odd choice. I always like it when I get in stuff that people don’t know. I love the Beach Boys — it’s a song that many people don’t know, “Our Prayer,” in Season 1, Episode 4, where they meet. I love the “Seabird” song by the Alessi Brothers, I think it’s the end of Episode 5 in Season 1.

Kate Bush has become one of my favorite moments [in Season 2], as a moment singular to just the show and the story themselves. It was also the visual of Stede coming down as a mermaid. It’s just so absurd, yet it’s so beautiful and so powerful at the same time. I don’t know how they do it, but they do it. I could watch that Fleetwood Mac scene over and over and over again in the end, the shot pulling back of them laying on the ground, and Stede goes, “You’ve come back,” and Ed is like, “I never left,” and then the wink. I love that moment so much. This show is just hands down one of my all-time favorite shows I’ve ever gotten to work on.

Image via HBO Max

Everyone I’ve talked to about working on this show is having an absolute blast.

PHILLIPS: I also think — I’m always talking highly of David, but he deserves it — it comes from the top down. That dude is super creative and very collaborative and also just kind, and that’s rare when you’re a showrunner/creator. He makes it such a pleasurable, fun experience with a lot of hard work, which is hard to do — to make people work really hard and challenge themselves, but then they want to do it because it’s fun and rewarding, not because someone’s cracking the whip.

All episodes of Our Flag Means Death are available to stream on Max.

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