The Trailer for 'Our Flag Means Death' Season 2 is Hilarious and Heartbreaking

Black Pete (Matthew Maher), Roach (Samba Schutte), Stede (Rhys Darby), and Wee John (Kristian Nairn) shelter under an overpass in the rain, all looking bedraggled.

Matthew Maher, Samba Schutte, Rhys Darby, and Kristian Nairn return in Our Flag Means Death Season 2.

Photograph by Nicola Dove/Max

Batten down the hatches and prepare to set sail! Our Flag Means Death has set a course for the release of its second season with a swashbuckling new trailer. The long-awaited second season from the genius minds (and surprisingly tender hearts) of David Jenkins and Taika Waititi will premiere this fall, and the trailer forecasts plenty of heartbreak and hilarity to measure up to the success of the show’s first season.

The show premiered in March 2022 and its humor and heartfelt queer representation instantaneously earned it a dedicated fanbase. The second season was announced in June 2022, and filming wrapped in December of that year. Prior to the official trailer, Max released first-look photos and a short teaser trailer.

Set to Patti Smith’s “Because the Night” (this show never misses with its soundtrack choices), the latest trailer reintroduces viewers to gentleman pirate Stede Bonnet (Rhys Darby), who ended last season by ditching his newfound sweetheart, the not-so-fearsome Blackbeard aka Ed Teach (Taika Waititi). Stede and Ed are back, hopefully, to kiss and make up, but not before plenty of swordfights, hijinks, and run-ins with baddies on the high seas.

Check out the full-length Season 2 trailer, which gives a sense of the plot.

Our Flag Means Death is, at its heart, a love story, but just as importantly, it’s the best kind of story of all, a found family story. That delightful family of pirate misfits will reunite for Season 2, with returning cast including Con O’Neill (Chernobyl) as Blackbeard’s nefarious sidekick Izzy Hands, Vico Ortiz (The Sex Lives of College Girls) as the mysterious Jim, Samson Kayo (Timewasters) as Oluwande, Jim’s sweet love interest, and the rest of the crew rounded out by Kristian Narin (Robin Hood: The Rebellion) as Wee John, Joel Fry (Game of Thrones) as Frenchie, Matthew Maher (Captain Marvel) as Black Pete, Ewen Bremner (Will) as Buttons, and Samba Schutte (The Grind) as Roach.

One yet-unannounced member of Stede's scrappy crew is everyone’s favorite scribe, Lucius, played by Nathan Foad (Bloods), who appeared to meet a watery end in Season 1. Eagle-eyed viewers can spot a figure resembling Lucius in the trailer, but there is no official word on his return. The ever-delightful Leslie Jones (Ghostbusters) will also reprise her role as Spanish Jackie.

New faces aboard Season 2 include some much-needed new female characters, including Madeleine Sami (Double Parked), Anapela Polataivao (The Messenger), Ruibo Quian (Manchester by the Sea), and Minnie Driver (The Witcher) as legendary historical pirate Anne Bonny.

In interviews with Vanity Fair conducted before the SAG/AFTRA strike, cast members Con O'Neill and Vico Ortiz teased their characters' journeys in Season 2 and what fans can expect from the season as a whole. Ortiz said that their character, Jim, "really evolves in season two… There's a bit more zaniness and a bit more softness."

O'Neill spoke about series creator David Jenkins' approach to the second season, saying, "I don't think David Jenkins is ever going to follow an expected route… I think [fans are] going to appreciate what [Jenkins] wants. Season two does stick to the original premise that we created in season one, which is take it on to other levels."

Season 2 of Our Flag Means Death will premiere on Max on October 5, 2023, with two episodes, and stream two episodes a week through the end of the month. Season 1 is available to stream on Max now.

Author Emma O’Neill-Dietel

Emma O’Neill-Dietel is a writer, educator, and history nerd from Philadelphia, PA. She eats, sleeps, and breathes Doctor Who but has been known to enjoy other British TV and movies too. She may love British media but don’t get it twisted; she’s Irish through and through. Follow her on Threads: @emmaod22.

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