The answer is quite simple: You can and should watch the “Pirates of the Caribbean” films in the order of their release … but you don’t necessarily have to watch every one of them.
Whichever way you decide to go about plundering the seven (cinematic) seas, your journey should assuredly start with 2003’s “The Curse of the Black Pearl.” It’s the entry that introduces most of the key players from the next four films and it more than suffices as a standalone story, should you decide this franchise just isn’t for you upon watching it. After that, it’s time to move on to 2006’s “Dead Man’s Chest” and 2007’s “At World’s End,” which are themselves halves of a two-part narrative and form a complete trilogy with “The Curse of the Black Pearl.”
Here’s where you can choose between two paths. 2011’s “On Stranger Tides” is a sequel to “At World’s End” and picks up a story thread left dangling at the end of that film (Jack Sparrow’s search for the Fountain of Youth). But at the same time, almost none of the new characters in “Stranger Tides” are brought back or referenced in the next film, 2017’s “Dead Men Tell No Tales,” and the actual plot has limited bearing on what goes down in the sequel that follows. It’s also reasonable to assume that future “Pirates of the Caribbean” films won’t be revisiting the events from “Stranger Tides” either, seeing as it’s not one of the more cherished installments among fans of the property.
Mind you, “Dead Men Tell No Tales” itself isn’t what you might call a fan-favorite, so why not just stop after the first three films? Well, just hear this crusty landlubber out.