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Our Flag Means Death Stars Vico Ortiz And Samson Kayo Talk Jim And Olu’s Perfect Pairing

HBO Max’s Our Flag Means Death features a perfect pair of friends and an obscene amount of humor. It is reimagined history at its best.

Our Flag Means Death
Courtesy of HBO Max

There are a few constants in this world: death, taxes, and the brilliance of Taika Waititi. The JoJo Rabbit and What We Do In The Shadows writer just has “it”. His ensemble stories are so compelling, the humor perfectly absurdist, and the characters are meticulously well drawn. Everything he touches turns to comedy gold. HBO Max’s latest series, Our Flag Means Death, from creator David Jenkins is a prime example. Waititi directed two of the episodes and stars as Blackbeard. He is reunited with fellow Shadows star Rhys Darby as a literal fish out of water.

The comedy series is a fictionalized version of the real-life of the most famous pirate on the seas and Stede Bonnet, otherwise known as the Gentlemen Pirate. In much the same way that STARZ’s incredible Black Sails breathed new life into the Johnny Depp era of pirating, Our Flag Means Death captures that same lightning in a bottle to produce a spit-take-inducing bit of hilarity that is also surprisingly heartfelt. That is largely due to the chemistry between Samson Kayo’s Oluwande and Vico Ortiz’s Jim. They are the unlikely heart and soul of this ragtag bunch of degenerates who help steer the ship when everything threatens to become too silly. Recently I got the chance to sit down with Kayo and Ortiz to talk about the series and what we should look out for in the weeks to come.

Both Kayo and Ortiz were drawn to the unconventional freshness of the series. The series which could easily be described as a comedy is so much more than that. Ortiz liked “how much heart there is”. They further explained that the fact that Our Flag Means Death wasn’t “shying away from any conversations” was a big draw for Ortiz. “Seeing everyone dive into these characters and relationships with such depth and warmth. It was beautiful to be part of,” Ortiz said. Kayo said he “hadn’t read a script like it. It was exciting to see where we’re going [to] go. That’s the beauty of it.”

The well-balanced episodes and series certainly keep you guessing. There are whole segments devoted to deep conversations, clever deceptions, semi-brutal violence, cheeky comedy, and meaningful life questions. Each component is woven perfectly into the intricately paced story making each moment as crucial as the last. The complexity of the script and the genuine abandon with which everyone throws themselves into their roles is a highlight.

When asked about their fantastic costumes, both were enthusiastic. Ortiz, who is gender fluid non-binary, said they loved expressing what it means to be “masculine and feminine on my own terms”. Finding Jim’s signature hat was a “gender euphoric moment”. Ortiz further said that they felt “pretty and sexy and masculine” dressed as Jim. On the other hand, Kayo wanted his costume to feel like his character. He “needed to feel more relaxed and calm.” Getting into his freeing long open trousers each day was a breeze compared to Ortiz, who he said was dressing for hours.

Our Flag Means Death
Courtesy of HBO Max

Just because Our Flag Means Death is a comedy doesn’t mean there isn’t a fair amount of fighting. Pillaging is what pirates do best, after all. Although the Gentlemen Pirate avoids violence whenever possible, there is only so much the gentile man can do. A pirate ship sometimes has to defend itself. While Ortiz’s Jim didn’t get to have as many fight scenes as they would like, Ortiz is waiting for that epic fight scene with Con O’Neil’s Izzy Hands that they teased we could see in Season 2 if HBO gives them a pick-up. Preparing for Ortiz’s fight scene with Leslie Jones was “truly amazing”.

Our Flag Means Death is uniquely funny, and after talking with them just a short time, it was easy to see what drew them to the series. It is also obvious that the chemistry their two characters share is echoed in the actors. Ortiz describes Jim as an “unhinged firecracker” and Olu as “zen and chill.” The best duo around is an odd couple brought together by circumstance and a “love that we have for each other”. The pair which could have been lost in a tidal wave of insanity on a series like this shines because of their “relationship [that] grows stronger as each episode goes on because of the adversities that we both face during the season. It’s nice to see it play out organically”, Kayo said. The evolution of the two is worth watching for alone.

Lastly, when I asked if either of them had any wanderlust in their hearts they had surprising answers. Both Kayo and Ortiz said they could have been pirates. Ortiz is a sailor fencer from the Caribbean, and Kayo thinks he would be a “clever” pirate. The pair has palpable chemistry that only grows stronger each episode. The first three episodes aired last week on HBO Max, with a new episode released weekly after that. Our Flag Means Death is the kind of series that will reach cult status in much the same way as What We Do In The Shadows. The lines are fast and witty, and the cast is exemplary and features easily the best duo on television. So walk the plank and head to shore. You can’t miss this premier series.