The Dread Pirate Roberts meme originates from the 1987 cult classic film 'The Princess Bride,' based on William Goldman's novel. The character is a feared pirate identity passed down from one man to another to maintain an air of immortality and terror. The most iconic scene used for memes features Westley, played by Cary Elwes, telling a captured farm boy, 'Good work. Sleep well. I'll most likely kill you in the morning.' In internet culture, the meme is often used to represent demanding bosses, cynical encouragement, or the idea of a title that transcends an individual. It captures the dry humor and legendary status of one of cinema's most beloved swashbucklers.