What’s the difference between a pirate and a drag queen? Pirates live at sea, pillaging and plundering every day. Drag queens live on the stage, singing their hearts out to a captive audience. Their lifestyles might be different, but some boundaries are meant to be broken. Just look at Our Flag Means Death. Max’s pirate comedy has become a favorite of the LGBTQIA+ community, with the stars embracing their status as queer icons.

In fact, some of the cast members have considered taking it a step further. During a panel at Florida Supercon 2023, Con O’Neill says he would love to try performing in drag but wasn’t sure where to start. This turned into a fun discussion where each cast member imagined what song they would perform, and what song their OFMD characters would perform.

“As Lucius I would like to do 'Sorry Not Sorry' by Demi Lovato. I think that’s very Lucius,” Nathan Foad says. Foad then speaks about the song he would sing as himself. “I don’t think any of you are going to be expecting this. Does anyone know that song 'Miss Otis Regrets'? The Ella Fitzgerald version.”

“Just to be in character, I guess Wee John would do 'Firestarter',” Kristian Nairn says. “And me, that’s not really a hard question because I’ve done it. I think the first song I’ve ever performed in drag in real life was 'Freak Magnet' by L7. “

“As Izzy I would do 'I Am What I Am'. And I’m going to do it now,” Con O’Neill says. He then stands up and pretended that he was about to perform. “No, I’m not,” he playfully said as he sat back down. The audience erupted in laughter and applause.

Watch the full Our Flag Means Death panel from Florida Supercon 2023 panel now!