The main characters, ranked by sympathy

Our flag means death follows real-life characters like Stede Bonnet and Blackbeard, but it’s a lot more comedic than these men’s deeds would indicate. While history has shown these two pirates and their crew to be pretty goofy, the HBO Max series shows them as real people, with genuine interests and individualized flaws.

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This means that some will be friendlier than others. The ensemble comedy features great banter between Bonnet’s crew on the Revenge, and some manage to come off as endearing by showing their compassion. The show is about small moments, and there are plenty of big ones.

ten Calico Jack (Will Arnett)

Will Arnett as Calico Jack in Our Flag Means Death

Will Arnett is one of Our flag means deathis one of the most recognizable guest stars and his presence is always welcome. Calico Jack’s character, however, is the opposite.

Calico Jack almost immediately tries to wedge a wedge between Bonnet and Blackbeard, even going so far as to urinate on the former’s shoes. He also shows no remorse after murdering Buttons’ seagull friend and deservedly gets the boot of the Revenge.

9 Mary Bonnet (Claudia O’Doherty)

Stede Bonnet's marriage to Mary in Our Flag Means Death.

Claudia O’Doherty is a very likeable performer, and her character Mary’s marriage to Bonnet is hard for both of them to see. It’s an arranged marriage and neither wants it before or after they meet.

Then, one day, her husband drops the bomb that not only wants to sail the high seas on a boat, but is already being built. Luckily, he makes the decent decision to give it all up to her, but the brief time viewers spend with Mary shows that she’s a kind and gentle person, and they’re happy for her delayed but true happiness.


8 Buttons (Ewen Bremner)

Buttons looking out to sea with Steve on Our flag means death

Buttons is always at his captain’s side, even when his captain is as incompetent as Bonnet. But Bonnet trusts the man completely and often asks his advice, at least until Blackbeard comes on the scene.

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Although he thinks of eating others even in less difficult times, he is overall a gentle soul. This shows in his interactions with Karl, who is arguably Buttons’ best friend, even on Bonnet. Karl is also a seagull, but he proves to be just as useful as any pirate aboard the Revenge.

7 Black Pete (Matthew Maher)

Matthew Maher as Black Pete in Our Flag Means Death

Black Pete is nothing if not the source of a good story, even if it is entirely fabricated. He regales the crew with his adventures with Blackbeard the legendary and enigmatic pirate. It all makes no sense, but he soon gets his chance to make the lie real.

Fueled by a fun and believable performance from Matthew Maher, Black Pete also seems like a healthy partner for Lucius. He’s still a pirate who doesn’t always seem particularly averse to the craft, but at least he’s nice to his co-workers and his partner.

6 Little John Feeney (Kristian Nairn)

Wee John sitting on the deck of The Revenge on Our Flag Means Death

Kristian Nairn, from the HBO series game of thronesdoesn’t have much to do Our flag means deathbut his Wee John Feeney is quite a kind pirate even if he has a penchant for burning people alive.

Feeney is the kind of guy to stand up for his friends, but that doesn’t go that far with a pirate, and his love for the flame makes him a liability. Even still, he is very friendly if he is on your side.

5 Lucius (Nathan Foad)

Rhys Darby as Stede and Nathan Foad as Lucius in Our Flag Means Death

Lucius marks the first major role for comedian Nathan Foad, who gets a lot of the screen time in the first season of the HBO Max pirate comedy. He’s Captain Bonnet’s scribe, and he struggles with the job because the captain has trouble knowing what he’s doing let alone articulating it.

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Lucius is a charming presence as well as an overall lovable guy. He’s not trying to bring anyone else down or even harm, which is usually a hacker’s daily bread. Instead, Lucius just lives, and he even keeps his promise not to expose “Jim”‘s true identity to the rest of the crew, despite having several options to do so.

4 Blackbeard (Taika Waititi)


Responsible for some of Our flag means deathTaika Waititi’s deepest quotes, Edward Teach aka Blackbeard is almost the most likable character on the show. However, two factors hold him back.

In reality, Teach and Bonnet separated, with Teach accepting a royal pardon. That’s what happens on the show as well, and Waititi’s Blackbeard does what the real man did by quickly returning to hacking. Blackbeard from the series is hurt, feeling betrayed by Bonnet. They were supposed to start their life together, but Bonnet is nowhere to be found. He was kidnapped, but Blackbeard thinks it’s just a case of abandonment. He loses a lot of sympathetic points when he does the same with Bonnet’s crew by stranding them on a desert island to die there. Additionally, Blackbeard lies to Bonnet earlier in the series about his murder history, claiming to have killed none. However, this was revealed to be a lie by Calico Jack, and the ease with which Blackbeard is able to pull it off makes the viewer wonder how much of his cruelty he really put behind him.

3 Bonifacia “Jim” Jimenez (Vico Ortiz)

Vico Ortiz as Bonifacia Jim Jimenez in Our Flag Means Death

One of Our flag means deathBonifacia Jimenez’s smartest characters board the Revenge as “Jim”, a quiet man of expert combat prowess. While Jimenez ends up keeping the shortened name even after being exposed, their fighting ability remains the same.

Jim is on a warpath seeking revenge on the people who killed their families, and the character’s arc is both one of the strongest in the first season and one of the most exciting in the second.

2 Stede Bonnet (Rhys Darby)

Stede Bonnet smiling in Our flag means death.

Stede Bonnet, “The Gentleman Pirate”, was born into money. This is true for both the actual figure and Rhys Darby’s admittedly more humorous take. Darby’s Bonnet does what the real man did and turns his back on his wife for a life of piracy. There’s something admirable about getting started, but Bonnet would be far less likable without Darby’s bubbly, cheerful performance.

Bonnet’s interactions with his crew are always respectful, but he seems like someone out of his element, because that’s exactly what he is. When Blackbeard comes on the scene, Bonnet ends up becoming even more likable, mostly because the series focuses a little more on their relationship than on their plunder of merchant ships.

1 Oluwande (Samson Kayo)

Samson Kayo as Oluwande in Our Flag Means Death

Oluwande is Revenge’s unofficial mediator. When the violent crew becomes unruly, or even plots to kill their own captain, they step in to make more level heads prevail.

He’s the only one initially aware of Jim’s truth, and he backs it up in a way that the viewer knows without a second thought. The crew again plots to overthrow their captain, a position that is now filled by Izzy. It’s obvious to everyone on the team the same as it is to the public: once Izzy is out, Oluwande is in.

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