Since Fifth Business is Dunstan Ramsay's autobiography, he is the main character. Most of the other characters appear only as their lives and identities impinge on his. They are not characterized in a conventional novelistic way. The most developed character is Boy Staunton whom Ramsay calls his "lifelong friend and enemy" in his first reference to him in the second sentence of the novel. Staunton is the man who is successful in worldly terms. He has insured Ramsay's material well-being, since his early investment tips have enabled Ramsay to build a nest egg over the years. There is something romantic in Boy Staunton. After World War I, the Prince of Wales becomes his role model: "Flaming Youth, and yet, withal, a Prince, remote and fated for great things. Just the very model for Boy Staunton, who saw himself in similar terms." For Staunton, having more and looking better than any of his rivals are major concerns. He uses Ramsay as his confidant, which permits Ramsay to see what goes on in Staunton's social and domestic life. At home, Staunton creates a classic dysfunctional family: He thinks of his wife Leola as a failure, unsuited to her social station, and tries to remodel her; he spoils his daughter Caroline, praising her extravagantly for her good looks; and he nervously watches his son David for any signs of unmanliness. In business, Staunton cultivates a number of "clean-cut" young rising executives whose stars fall when they marry and bring their wives to dinner at Staunton's. Ramsay sees sex as playing "a dominating part" in Staunton's life, but Staunton as being totally unaware of it, regarding Freud as "a madman" for "bringing everything down to sex the way he did." After the abdication of King Edward, Staunton's hero, Boy goes into a funk and leaves his family temporarily, sending Leola into a suicidal tailspin when Ramsay rejects her advances.

After World War II and the death of Leola, Boy Staunton becomes involved in public life. He thinks that he can solve Canada's problems by applying business principles to the government. He does not do too well with the electorate because he cannot hide his contempt for the common man and he is too handsome for a politician, but he draws the attention of Denyse Hornick who manipulates him into marrying her and campaigning for the position of Lieutenant-Governor of Ontario, an appointed position that is mainly ceremonial and is costly to whoever holds the post. He is on the verge of achieving his goal when he dies mysteriously, his body found in the driver's seat of a submerged car in Toronto harbor with a stone in his mouth. His death precipitates Dunstan Ramsay's heart attack when Dunstan hears himself identified by the Brazen Head in Magnus Eisengrim's magic show as one of Staunton's murderers, "the inevitable fifth, who was keeper of his conscience and keeper of the stone."

Mrs. Dempster's life is so intertwined with Ramsay's mythology that it is difficult to see her as a character in her own right. As presented by Ramsay, she believes that she saves the lives of men when they are lost. In three miracles, she brings Ramsay's brother, Willie,...

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