Dread Pirate Roberts

The Dread Pirate Roberts is an unseen villain in The Princess Bride. He is a feared pirate-lord who, according to Buttercup, has been marauding the Seven Seas for twenty years. His ship is called the Revenge. He is notorious for never taking prisoners.

At the beginning of the film, when Buttercup's beloved, Wesley, decides to seek his fortune as a sailor, his ship is attacked by the Revenge, and due to Roberts' reputation for never taking prisoners, Wesley is presumed killed, leaving Buttercup heartbroken.

Five years after Wesley left Buttercup, when Buttercup is kidnapped by Vizzini and his cohorts (Fezzik the Giant and Inigo Montoya), they are followed by the Revenge, and a mysterious man in black from the ship claims to be Roberts. The Man in Black defeats Inigo in a duel and also overcomes Fezzik in a one-on-one hand fight, and even defeats Vizzini in a fatal battle of wits allowing him to capture Buttercup from them. After getting a ways with Buttercup, she correctly assumes that he is Roberts, and wishes death upon him for killing Wesley. Roberts then recounts his confrontation with Wesley and claims that he died "well", saying that before he died he very simply asked to be allowed to live because of his love for Buttercup; he then insults Buttercup for supposedly insulting Wesley's memory for now being engaged to another (Prince Humperdinck), which provokes Buttercup into angrily pushing him down the side of a mountain. After she does this, Roberts says "As...you...wish!" revealing that Roberts, was in fact, Wesley.

When Wesley and Buttercup enter the Fire Swamp, he goes on to explain exactly how he had taken the identity of the Dread Pirate Roberts: when his ship was attacked, he indeed asked Roberts to live for the sake of Buttercup, and, in actuality, Roberts allowed him to live and become a member of the Revenge 's crew, but said that he would "most likely kill [him] in the morning." Wesley remained a member of the crew for several years and eventually became friends with Roberts, before Roberts told Wesley a secret: that he was, in fact, not the real Dread Pirate Roberts. His name was Ryan, and he had inherited the name from the previous Roberts (who was not the real Roberts either, and was actually a man named Cummerbund.) Wesley explains that the real Roberts had in fact been retired for 15 years, and his name had now become a title passed on from successor to successor ("No one would surrender to the Dread Pirate Wesley".) Ryan wanted to retire and give the title to Wesley, and now that he was reunited with Buttercup, Wesley announced that he planned to retire and give the title to someone else.

Later in the film, when Wesley, Inigo and Fezzik try to infiltrate Humperdinck's castle to try and stop his marriage to Buttercup, Fezzik dresses up in a holocaust cloak (and is also set on fire for scary effect) and pretends to be Roberts to intimidate Yellin's men; however, this version of "Roberts" is much scarier and is more akin to a Grim Reaper-esque figure, but produces the desired effect in scaring off Yellin's men and enabling the three of them to get into the castle.

At the end of the film, when Buttercup has been rescued, Inigo reveals that, now that he had finally avenged his father by killing Count Rugen, he had no idea what to do with the rest of his life since he had been pursuing revenge for so long. Wesley tells Inigo to consider piracy, as he would make a "wonderful" Dread Pirate Roberts. It is unknown if Inigo follows through on this offer and becomes the new Roberts, or if the title went on to someone else.