The Princess Bride is the fairy tale story of the romance of Buttercup and her childhood sweetheart Westley. Just as with most fairy tales, the road to true love is not an easy one. When Buttercup rebuffs Westley affection for her, he decides to leave home on sail on the seas, where he is captured by the Dread Pirate Roberts. As Roberts is about to kill Westley, Westley tells him of his true love, which moves Roberts to spare Westley's life.

We soon find out that the real Dread Pirate Roberts hasn't been around for a long time and he did as each of his successors did and passed on the name for the chosen man to carry. As is tradition Westley is chosen to take over for the current Dread Pirate Roberts. This requires Westley to learn all the necessary skills, such as fencing and pillaging that are suitable to carrying the name of a famous pirate.

Prince Humperdink, who has become attracted to Buttercup because of her purity of heart, decides to pursue her as a wife. What Buttercup did not know, though, is that Humperdink intends to marry her only to murder her in order to instigate a war with their rival country, Guilder. The prince orders his servants to snatch Buttercup before the ceremony as she is out riding her horse and thinking of her one love, Wesley.

The henchmen, lead by the self-proclaimed genius Vizzini, transport Buttercup to the border with Guilder. While at sea, they find they are being followed by a mysterious ship. Upon reaching the shore, they climbs steep cliffs to escape. A passenger from the ship climbs after them, and the kidnappers are amazed at the stranger's strength and persistence.

Once they are at the top of the cliffs, Vizzini tells Fezzik to smash him by sending rocks falling. When that does not work, Vizzini sends in Inigo Montoya, the swordsman, to wait for the stranger to kill him. When the stranger and Inigo duel, both exhibit great skill in fencing, each acknowledges great respect for the other's skill. Eventually the stranger wins the duel, knocking Inigo unconscious instead of killing him.

So, the man in black continues to follow the princess and her abductors. He catches up with Vizzini, who challenges him to a battle of wits. Since the man in black has an immunity to this poison, he lives, but Vizzini dies. So then the princess has to travel with this stranger. She tells him how unlike her true love he is- her true love would never hide behind a mask. Then she figures out that the man in black actually is her true love.

Evil Prince Humperdink shows up shortly after they reunite. He takes Westley to a dungeon where he is tortured to near death and he forces Buttercup to continue arrangements for marriage. A local magician is able to revive Westley following his suffering. Once he has enough strength he and his friends Inigo and Fezzik save the Princess Bride from her vicious fiance.