For Fans of Black Sails

Most pirate captains in fiction are charming rogues. James Flint is not. Black Sails commits to showing a man who has made himself into a weapon in service of a cause he can barely articulate, and who destroys nearly everyone around him in the process. The show earns its prequel status because by the time the Treasure Island timeline begins, you understand exactly what that rage cost. If that kind of character study appeals, Deadwood's Al Swearengen and Peaky Blinders' Tommy Shelby occupy the same moral register: people who built something out of nothing, at terrible cost.

The show's most underrated move is treating Nassau not as a backdrop but as an experiment. For a decade, it functioned as a place where the rules of empire did not apply. Black Sails asks whether that freedom was ever sustainable, and the answer is a sustained tragedy. For readers who want to go deeper, Colin Woodard's The Republic of Pirates (nonfiction) covers the real historical Nassau and the actual figures the show draws from, including Charles Vane and Anne Bonny.

Assassin's Creed IV: Black Flag is the obvious recommendation, and it is genuinely great: the open Caribbean, sea shanties, a story that takes the pirate republic seriously. But Pillars of Eternity II: Deadfire does something closer to what Black Sails does narratively: it gives you factions with incompatible legitimate claims, forces you to pick a side, and lets you lose. The naval combat is tactical rather than action-based, and the writing never flinches from consequences.

Most seafaring films romanticize the ocean. Peter Weir's Master and Commander (2003) does not. The ship is cramped and cold; the surgery is awful; the command decisions are cruel and usually correct. Russell Crowe's Aubrey has more in common with Flint than with Will Turner: a man who loves the sea because it is the only place where his authority is absolute and his particular kind of intelligence is worth anything. The Patrick O'Brian novels it adapts (starting with Master and Commander) are among the best historical fiction ever written.