Loosely based on a true story, Our Flag Means Death is a period rom-com set during the Golden Age of Piracy in the 18th century and follows Stede Bonnet, called the Gentleman Pirate, an aristocrat who gives up his cushy lifestyle to be a pirate and is, unsurprisingly, not very good at it. The series premiered in March 2022 on streaming service Max and has run for two seasons so far, and although a third hasn’t been announced, the show’s success and critical praise makes it likely.
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While Our Flag Means Death certainly centers Stede and his relationship with notorious pirate Blackbeard, the show features a large cast of characters all hilarious in their own ways, from Stede’s crew to the others they encounter along the way. While some are antagonistic, others are downright lovable and endearing, and they all have their quirks and eccentricities—perfect for a life of piracy.
9 Izzy Hands
Played by Con O’Neill
Image via Max
Israel “Izzy” Hands was Blackbeard’s—real name Edward Teach—first mate, and he was determined to help the notorious pirate maintain his reputation and often sabotaged his attempts at leaving the persona behind. Izzy was particularly worried about how his relationship with Stede would play out. After being taken captive by Prince Ricky Banes and escaping, Izzy was shot in the stomach and died in Ed’s arms.
Izzy was a complex character who experienced a lot of growth over the course of the show’s two seasons—while he was more of an antagonist in Season 1, that wasn’t exactly the case in Season 2, which showed a different side to him. When left in charge of the Revenge, he proved to be a cruel captain, so much so that the crew staged a mutiny. But no matter what, he was always loyal to Ed and simply wanted the best for him.
8 Wee John Feeney
Played by Kristian Nairn
Image via Max
Wee John Feeney is a loyal member of Stede’s crew on the Revenge. Much of his past remains a mystery, and in fact, he doesn’t really do a whole lot as a crew member. After Izzy became captain, John participated in the crew’s mutiny—with their intentions to drown Izzy, John carried the anchor tied to his feet. John, along with the rest of the crew, was stranded on an island after Blackbeard’s return.
John has a curmudgeonly persona and a touch of pyromania—especially when the thing he’s setting on fire is people. Still, he’s fun to watch and is generally something of a gentle giant with a softer side that’s unusual for a typical pirate, as he owns a doll and used to sew dresses for his mother, a skill he applies to sewing things like flags aboard the ship and his own clothes.
7 Lucius Spriggs
Played by Nathan Foad
Image Via HBO
Lucius Spriggs is a crew member on the Revenge, in charge of keeping records and documenting the crew’s adventures, as he’s the only one—other than Stede himself—who’s able to read and write. He was presumed dead at the end of Season 1 after Ed pushed him from the ship into the ocean, but he was ultimately revealed to be alive in Season 2. He struck up a romance with Black Pete, and the two married at the end of Season 2.
Lucius is quick to notice the chemistry between Stede and Ed and sort of acts as their matchmaker, encouraging them to express their feelings for one another. While his shipmates are eager to jump to violence, Lucius is more cautious and unwilling to take things to that level—and on top of that, he’s easily disturbed by many things, blood included. In Season 2, his experiences lead him to mature but also become more cynical.
6 Frenchi
Played by Joel Fry
Like almost all the rest of the crew of the Revenge, Frenchie can neither read nor write, and instead communicates through drawings when necessary. He is also a musician, often seen playing music and singing, typically with dark lyrics about the crew’s adventures. At the start of Season 2, Frenchie is among the crew now under Blackbeard’s command, forced to carry out whatever heinous acts he orders and temporarily serving as his first mate when Izzy can’t. By the end of the season, he’s the new captain.
He and Roach may think of themselves as “men of science,” but in reality, Frenchie is deeply superstitious—not surprising for a pirate. He’s also a bit of a grifter, known for hilarious schemes. All of this makes him fun to watch, but it also makes it hard to picture him as a captain, at least a functional one. Then again, that wouldn’t be a first for Our Flag Means Death.
5 Oluwande Boodhari
Played by Samson Kayo
Oluwande is part of Stede’s crew on the Revenge. His best friend on the ship is Jim, and the two became more than just friends and began a romantic relationship. The two were separated in Season 2 in the aftermath of Stede and Ed’s split, as Jim joined Blackbeard and Oluwande was left stranded on an island with the rest of the crew. As the season progressed, they pursued other relationships, with hints of a possible polyamorous relationship blossoming after they were reunited.
Oluwande is an overall good guy—he’s reasonable and level-headed, sometimes taking a diplomatic approach to solving problems. He’s also kind-hearted yet brave, as well as trustworthy, as shown by the fact that initially, he was the only one who knew the truth about Jim’s identity, forming the basis for their relationship. On top of that, he’s a good, loyal friend who wants Jim to be happy, whether or not that’s with him.
4 Jim Jimenez
Played by Vico Ortiz
Image via Max
Revenge crew member Jim was born in St. Augustine, and as a child, their entire family was killed by a group of roving outlaws, leading them to be raised by nuns. Jim is non-binary. In order to avoid pirate Spanish Jackie, played by Leslie Jones, who has a bounty on their head after they killed her favorite husband, Jim initially dons the disguise of a fake beard and nose aboard the Revenge and pretends to be mute, with only Oluwande aware of the truth. When the crew eventually finds out, they are accepting of Jim’s identity.
Jim is one of the most interesting characters on Our Flag Is Death, largely because of their backstory. They are a tough, capable fighter, motivated by the murder of their family and their desire for revenge with skills they learned from the nuns who raised them. Because of their efforts to dodge Spanish Jackie, they’re also quite guarded—but as they begin to let that guard down, they’re compelling to watch.
3 Nathaniel Buttons
Played by Ewen Bremner
Buttons is Stede’s first mate on the Revenge, helping him navigate the world of pirates. While not much is known about his past, he’s an experienced sailor. He’s good friends with Karl, a seagull, who often sits atop his head and assists him with lookout duties. Following Stede and Ed’s breakup, Buttons was among the crew abandoned on an island. He apparently successfully performed an “avian transmogrification” spell and transformed himself into a seagull.
Buttons is by far the strangest character aboard the Revenge, as he’s very superstitious and has a number of interesting quirks—including basking nude in the moonlight—but that just makes him a hilarious part of the show, and his transformation into a seagull was a hilarious, over-the-top part of the series. But there’s more to him than that. He’s also loyal to Stede, who places immense trust in him, and is a crucial part of his crew.
2 Ed “Blackbeard” Teach
Played by Taika Waititi
Image via Max
Blackbeard is a notorious pirate, feared across the seas—but when he’s introduced in Season 1, he’s growing tired of the life and is ready to retire. When Izzy tells him about Stede, he decides to go looking for him, and after meeting, the two become friends, fall in love and agree to run away together, but Stede instead returns to his family. In Season 2, a heartbroken Ed returns to piracy, and ultimately, the two reunite at the end of the season.
Ed is charismatic and charming, with a soft side, despite being a pirate—even if he is oblivious to Stede’s romantic advances. But of course, Ed’s reputation isn’t for nothing—he also has a dark side, shown through his actions as a pirate. He often resorts to violence, and his return to piracy in Season 2 is perhaps even more extreme than before, with his behavior becoming more extreme and showing just how cruel and callous he can be.
1 Stede Bonnet
Played by Rhys Darby
Image via HBO Max
Stede Bonnet is the captain of the Revenge who took up life as a pirate after abandoning his wife and children and leaving behind his aristocratic lifestyle. He was born in Barbados and was bullied as a child, including by his own father. As captain of the Revenge, he meets Blackbeard and falls in love, and the two plan to run off together, but Stede, guilty over leaving his family, has second thoughts.
Stede may be intelligent, but he is naive and completely unprepared for life as a pirate, lacking any of the skills that he’d need. He’s also immature, particularly when it comes to his relationship with Ed. But what he lacks in skills he makes up for with charm, as he’s also hilarious and endearing. His complex personality makes him the best character on the show. Although he turned to life on the seas, he hasn’t totally let go of his aristocratic tendencies and likes to dress nice and stay well-groomed and generally presentable.
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