The Dread Pirate Roberts: Greatest Legend of the Seven Seas (2006)

This is one of the most clever documentaries about the origins of the Dread Pirate Roberts’ mystic as one will find. Packaged on the “Buttercup Edition” of “The Princess Bride” DVD from 2006, this 11-minute short interviews four experts about how the Dread Pirate Roberts and Bartholomew “Black Bart” Roberts from the early-1700s could be historically similar characters. What pushes this quite by-the-numbers documentary apart from other intellectually mundane subject matters is that one of the “experts” happens to be… an imposter. No spoilers in this review but suffice to say, somewhere on this IMdB page has the answer to the riddle.

The documentary is concise, clever, and interesting on the Black Bart data. It gently nods to the historical accuracy/comparisons between the Dread Pirate and Black Bart being, quite possibly, one in the same. If you can find this gem on DVD, it is worth the exercise. Quite entertaining in exactly the same tongue-in-cheek manner “The Princess Bride” uses in it’s presentation of classic fairy tales with a touch of whimsy and sense of humor mixed into generally accepted fairy tale canon. Much recommended!