The Dread Pirate Roberts

In the film The Princess Bride, the Dread Pirate Roberts is the most feared pirate in the world. For 20 years he raided shipping between The New World and Europe in his ship Revenge leaving no survivors. <not a nice bloke!>

He was however more than one person.

The initial Dread Pirate Roberts made so much money in the first five years of his career that he retired (living like a king in Patagonia), passing on the name and the ship to his 1st mate Clooney. After Clooney got rich, he passed the name and ship to a bloke called Cummberbund who in turn passed them onto Felix Raymond Ryan. Ryan passed the name onto the hero of the Princess Bride Westley who made his fortune before returning to the events of the film and his true love. <Aaaaaaaaaaaaaah!> Does technically gloss over the fact that Westley (the hero) must have slaughtered hundreds of people while playing the role of 'The Dread Pirate Roberts'.

Inigo Montoya may have taken over as Roberts after the end of the film since Westley was retiring to be with Buttercup.