Oliver is the eldest son of Sir Rowland de Boys, and his heir.
Detesting his youngest brother for no reason that he can himself fathom, Oliver refuses to educate him, keeps the money he is due away from him, and plots his death. He is scornful and malicious, not above spreading lies about Orlando to convince Charles to have no mercy when wrestling with him, and envious that people love Orlando more than they do him. Incensed by Orlando’s beating Charles, he plans to burn Orlando to death in his sleep. When Orlando flees, Oliver is charged by Duke Frederick to find him, on pain of exile, with all his valuables held as surety in the meantime. Admitting to his hatred for his brother merely has him thrown out. He seeks Orlando till his beard has grown unkempt and his clothes ragged. Falling asleep, he suddenly wakes to find Orlando busy fighting a lioness that was waiting to eat him. He reconciles himself with his brother, and is sent by him to explain to Ganymede why he cannot appear himself. He is somewhat suspicious of Ganymede, not believing his protestations of counterfeiting when he faints; he also falls thoroughly in love with Aliena, woos her, and convinces her to marry him in an instant, intending to give all of his wealth to Orlando and to live with her as a shepherd.