Captain Blood (1935)

Few films manage to balance cheerful high-seas adventure with a pointed jab at authoritarian rule quite like Captain Blood. Directed by Michael Curtiz, this buoyant spectacle not only cemented Errol Flynn’s place in Hollywood but also introduced audiences to the first fully symphonic film score, courtesy of the legendary Erich Wolfgang Korngold.

Flynn’s mischievous charisma keeps the film afloat, even as it occasionally lingers too long on exposition. Based on Rafael Sabatini’s 1922 novel, Captain Blood marked the first of eight electric on-screen pairings between Flynn and Olivia de Havilland—one of which, The Adventures of Robin Hood, would become equally iconic. Here, Flynn commands Curtiz’s often densely packed frames with sweeping emotional gestures and an energetic physicality that makes him impossible to ignore.

However, the film’s third act takes a hard right turn into nationalism, abruptly shifting gears in a way that dampens its rebellious spark. The character we’ve admired for his defiance suddenly submits to the very system he spent the entire film resisting—an arc that feels forced, if not entirely dissonant.

And yet, I dare anyone to resist Flynn’s charm. Whatever missteps Captain Blood makes, its exhilarating action and undeniable levity make them easy to forgive. In the grand tradition of pirate films, this one still reigns supreme.

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Vertigo (1958)

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The Man Who Shot Liberty Valance (1962)