Review: Our Flag Means Death, "Pilot" & "A Damned Man" | Season 1, Episodes 1 & 2

It's a pirate's life for Rhys Darby and company in David Jenkins' HBO Max comedy

Image: Max

Welcome to Episodic Medium’s coverage of Max comedy Our Flag Means Death, which returns for its second season in October. With Max continuing to shorten its schedule with multiple episodes a week, we figured we’d take the opportunity to reflect back on the first season, so we’ll be posting reviews weekly-ish to fit it in before the premiere.

A reminder that all future reviews will be exclusive to paid subscribers, (except the second season premiere) and yearly subscriptions are 20% off until 9/15. You can find out more here.

---

The Golden Age of Piracy will never die in popular culture. Like the cowboys of the Wild West or the knights of the Middle Ages, there’s something about the era that resonates with an audience: the urge to take to the high seas and seek adventure, adopt elaborate personas and dress in lavish outfits, get involved in actions violent and profitable. It’s an atmosphere where the most famous participants have risen to near-legendary status, so much so that their stories practically belong to the public domain.

Despite the popularity of piracy stories, it’s an avenue that hasn’t been explored on television to the degree it has on film, where it runs the gamut from such classics as Pirates of the Caribbean: Curse of the Black Pearl and Muppet Treasure Island to such disasters as Cutthroat Island and most of the remaining Pirates of the Caribbean franchise. Starz’s Black Sails had a respectable four-season run but was largely absent from the critical conversation at the time, and NBC’s Crossbones is remembered solely (and barely) for John Malkovich’s seen-to-be-believed take on Blackbeard. Depicting the chaos and carnage of a pirate’s life is a bit outside the budget of most small-screen productions, which is why those shows spent the bulk of their time landlocked and their characters dealing with politics over pillaging.

HBO Max’s Our Flag Means Death doesn’t try to overcome those obstacles. If anything, it leans into them, coming across as less of a pirate show than a workplace comedy that happens to take place on a pirate ship. The trappings of the lifestyle are here—shipwrecks, sword fights, and kidnappings all take place within the first two episodes—but the real conflicts are the ones that are taking place on a smaller scale. It’s the heir to a proud comedic tradition, the stupidly overconfident employer dealing with a midlife crisis and a set of disgruntled employees, and adding the extra layer of having to overcome near-death experiences on a daily basis.

Created by David Jenkins of People of Earth, OFMD is loosely inspired by the real-life story of Stede Bonnet (Rhys Darby), a Barbados landowner who abandoned his comfortable existence to turn pirate. Bonnet has purchased a ship called the Revenge, staffed it with a full crew, and set out to be a different kind of pirate captain—the kind more dedicated to improving the character of his crew than leading them on bloody raids. Unfortunately, his crew signed up for the latter option when they became pirates, and most don’t think much of a career whose highlights are stealing potted plants and sewing individual flags. (They’re also not swayed by the amenities of the ship, including a “ballroom” that serves as storage for cannonballs. It’s good to see early proof that OFMD isn’t above stupid wordplay.)

Most of the comedy in the first two episodes is driven by the disconnect between Stede’s way of doing things and the way the piratical world works. “Pilot” features him trying to dispel threats of a mutiny by leading a raid on a larger target, only for that larger target to be an English warship, and one that happens to be captained by his childhood bully Nigel Badminton (Rory Kinnear). “A Damned Man” sees the Revenge run aground on a deserted island, Stede declaring a vacation for the crew, and the island turning out to not be as deserted as it looked on first glance. In both instances, Stede manages to fail upwards, first by inadvertently causing Badminton to fall on his own sword, and then managing to bluff his way past the far more qualified pirate Izzy Hands (Con O’Neill).

Image: Max

Despite the life-and-death stakes of both situations, the overall tone of OFMD is a gentle one, and there’s little tension to be found in Stede and company getting into these situations. Taika Waititi directed the pilot episode and is an executive producer on the series, and his unique sensibilities are shaping the show alongside Jenkins in early goings. The humor isn’t mean-spirited in any way save Badminton’s bullying—Kinnear is clearly having too much fun as the taunts grow more juvenile—and the gags are most reliant on fish-out-of-water dynamics. It’s also an anachronistic style of humor, with none of the dialogue making any attempt to be period-appropriate: Stede cheerfully proclaims “I’ll be your robber today!” while climbing into a fishing boat, and native villagers grumble “Fucking racist” when Stede and Black Pete wrongly assume said villagers ate their hostages.

That tone is in keeping with the character of Stede, who comes across in these first two episodes as a mixture of Ted Lasso, Michael Scott, and Murray from Flight Of The Conchords. It’s a portrayal that plays well to Darby’s strengths, as he’s an actor who always feels unnaturally chipper regardless of circumstance, and has such a likable quality you want to be rooting for him no matter how badly he’s doing. Each episode, a character tries to convince Stede that maybe the pirating life isn’t for him, and you do feel it coming from a genuine sense of concern on their part. It’s obvious to everyone participating and watching he’s in over his head, and they shrug off his death as an inevitability.

Crucially to the show, Stede’s not portrayed as oblivious to his situation—on the contrary, it seems clear he’s put as much thought into his circumstances as anyone else. Each episode has a series of flashbacks showing Stede as unhappy throughout his life: belittled by his father, bullied by Badminton’s thugs, judged by his wife. Jenkins said in an interview that he was driven by curiosity as to why the real Stede Bonnet turned pirate, and it looks like that’ll be the arc to be explored more as his career progresses. “A Damned Man” in particular shows the welcome potential in Darby to break bad, going from near-panic attack to his triumphant threat to Izzy: “I kind of enjoyed it.”

Image: Max

While Stede makes a solid impression starting out, most of his crew aren’t as well defined and can be sorted into two buckets. First, there’s there’s the violent ones who want to get back to some proper piracy, helmed by Black Pete (Matthew Maher) and supported by Wee John (Kristian Nairn), Roach (Samba Schute), and the Swede (Nat Faxon). On the other side, there’s the straight men who are mostly happy to get paid and go along with the nonsense, such as first mate Mr. Buttons (Ewen Bremmer), Oluwande (Samson Kayo), and Frenchie (Joel Fry). Falling in between is Lucius (Nathan Foad), who’s ostensibly closest to Stede as his unofficial scribe but seems to dislike him more than anyone else on the crew. (“I’m still in, by the way!” he cheerfully says after admitting Stede knows about the mutiny.)

There’s one clear exception to this: Jim (Vico Ortiz), who passes themselves off as mute with the rest of the crew, only to remove their beard and nose in private. If Stede wanted to start a new life on the Revenge, Jim is fleeing the consequences of some unknown revenge, with only Oluwande privy to the secret. Jim’s easily the most interesting of the crew members between this backstory, their obvious skill with a knife—the only real display of skill we get from Stede’s crew—and Oluwande being awful at hiding some level of attraction to them. It’s Jim who throws the knife to break the ruse with Badminton’s crew and trigger the climax of “Pilot,” and in “A Damned Man” they’re the one crew member with an arc when Lucius inadvertently learns their secret and runs for his life. The more of this we get from the rest of the crew, the better off OFMD will be in the long run.

And it’s reasonable to expect we’ll get more of that in the long run. Jenkins’s prior show People of Earth was a show with a strong island of misfit toys energy, and the pieces are definitely there for characters to define themselves as time goes on. Buttons gets the best one-liners (particularly when he goes off on a tangent naming sea creatures), Frenchie’s cheerfully fatalist songs make a great intro to the pilot (and are sadly missed in the second episode), and we can hopefully start a counter for how long it takes Wee John to burn something down.

Uniting the crew is also likely to be everyone’s best chance of survival, as OFMD downplays but doesn’t dismiss the level of danger in this world. If the first two episodes are about gradually building up Stede’s confidence and capabilities, they’re also about setting up that he’s a small fish in a big pond, and he’s about to meet with one of the biggest. “Pilot” ends with an optimistic sight, all four of his crew’s makeshift button-studded flags sharing equal prominence on the mast; and “A Damned Man” ends with the sight of Izzy Hands following the Revenge at the behest of his captain, the camera panning up to witness the flag of Blackbeard.

A flag that, unlike Stede’s, does in fact mean death.

Stray observations

• Yar, and welcome aboard Episodic Medium’s coverage of Our Flag Means Death! Thrilled to be joining this here crew of scurvy TV reviewing dogs, me old mates and fellow castaways from the deeply mourned wreckage of The A.V. Club. (I promise not to turn this into the Talk Like A Pirate section of this Substack.)¹

• Much like our Yellowjackets catch-up coverage, these reviews are written in mind for both new OFMD viewers and anyone rewatching before season two starts. Accordingly, I won’t be discussing plot points of later episodes in much detail, but will include a “Spoiler observations” section at the bottom for anything worth commenting on. Reminder, as always, to please tag comments with spoiler warnings if you want to get into those details.

• I like the variety of opening title cards introduced. “Pilot”: the titular flag waving in the breeze. “A Damned Man”: Kelp and seaweed washed ashore with the tide.

• The cast of this show is so varied and so interesting in their idiosyncrasies, that we’ll be introducing an episodic award of MVC: Most Valuable Crewmate, to see who’s the best at pulling their weight.

• MVC of “Pilot”: Feels only right to give the first award to Stede, for putting all this nonsense together and managing to sail out of it with the first win of his nascent piracy career.

• MVC of “A Damned Man”: Oluwande has the most going on this week as he gets a delicious cocktail, talks down the tribe from killing the wishy-washy Stede, and has some unresolved feelings for Jim.

• Mark Mothersbaugh composes the music for the show, and it goes a long way toward keeping the tone upbeat, his liberal use of the harpsichord somehow underlining the absurdity of the circumstances, while the solemnity of the cello showing the real emotions involved.

• Love the visual gag of the British officers’ spyglasses functioning essentially as a dick-measuring contest.

• Always great to see Gary Farmer show up, and his turn as the village chief is brief but fun as he makes the very logical conclusion that Stede’s crew isn’t a threat to anyone but themselves. Can’t fault him being careful though. “The eighth time? Shame on us.”

• “Raids are like snowflakes.” “No two quite alike?” “Well no, they almost always end in terrible bloodshed. Snowflake might not be the best comparison.”

• “There’s a kill, there’s a kill, another kill, oh, there’s your balls gone, and a kill.”

• “He’s holding his own head. That’s terrifying.”

• “This will eventually be a harpsichord! No, it kind of resembles a thin carrot.”

• “You can’t ‘call’ something in your mind. That defeats the purpose of calling.”

• “He’s gonna get you all killed.” “That’s very kind. And accurate.”

• Closing track for “Pilot”: “High on a Rocky Ledge” by Moondog.

• Closing track for “A Damned Man”: “Messa Da Requiem: Dies Irae,” by Verdi.

Spoiler observations:

• Discussing OFMD as a workplace comedy above does bury the lead that over the course of the first season, it becomes both a gay romantic comedy and one of the most progressive LGBTQ+ shows airing. We get a few hints of this early on—the reveal of Jim’s double identity, Lucius coming out to Jim in a desperate attempt to stay alive, Oluwande’s badly kept secret crush on Jim—yet they remain only hints of how much the show has yet to define its identity. It’ll be fun to watch that develop in coming weeks.

• We’ll obviously be talking a lot more about Taika Waititi as we go along. Like the show’s romantic streak, Blackbeard is underplayed in the first two episodes: mentioned by Black Pete in passing in the pilot, again in the cold open to the second episode as a near-mystical figure with glowing eyes and a head of smoke (“...when he needs it to be”), and then at the end when we learn he’s Izzy Hands’s captain. It’s a smart decision to ramp him up to a near-mythical status for when he finally makes his appearance.

1. MM here to note we could run one of these on International Talk Like a Pirate Day, though, at which point you’d have no choice.