Our Flag Means Death is a hilarious anachronistic pirate comedy on HBO Max. But the backstory of its main characters is surprisingly real. I talk with pirate historian Jeremy Moss, Purdue professor Manushag Powell and Jamie Goodall, staff historian at the U.S. Army Center of Military History, about how the historical figure of Blackbeard used theatricality to become a media phenomenon, and why it was an easy transition for people to believe he was a fantasy character versed in the dark arts. And we look at whether the endearing portrayal of the bumbling “gentleman pirate” Stede Bonnet in Our Flag Means Death is leaving out a crucial aspect of his backstory.