Guildenstern is one of Hamlet’s childhood friends and Rosencrantz’s closest companion. Although he is a minor character with only 29 lines in Hamlet, he is one of the two protagonists in Rosencrantz and Guildenstern Are Dead. His defining trait is his intellect. He is knowledgeable of “the great homicidal classics” (28), Socrates, and Zhuangzi, and he possesses an inquisitive, analytical nature that drives him to rationalize the people, objects, and phenomena around him. He earnestly believes that there must be a rational explanation for everything and that people should turn to rationality “as a defense against the pure emotion of fear” (13). Ironically, his penchant for rationalization drives him to emotional extremes, as he constantly experiences absurdity. His inability to establish certainty amidst chaos enrages him to the point of verbally abusing Rosencrantz on several occasions and attempting to kill the Player.

While Guildenstern can be aggressive, he has moments of tenderness with Rosencrantz, whom he clearly loves. He often comforts Rosencrantz in Rosencrantz’s moments of despair, as seen in Act III when he says, “Don’t cry...it’s all right…there…there, I’ll see we’re all right” (96). Guildenstern may find Rosencrantz to be aggravating at times, but he is never annoyed by his companion for more than a moment.