Orlando is the younger son of the deceased Sir Rowland de Boys and brother of Oliver. He is brave, chivalrous, tender, modest, smart, strong, handsome and beloved by all. He resents the harsh treatment he receives at Oliver's hands and complains that Oliver is neglecting to educate him; Orlando feels that he is being kept like livestock. Despite this neglect, Orlando's talents and his aristocratic nature reveal themselves, and he becomes his father's favourite. He has a will to attain knowledge and wanted to go to school. Nevertheless, he is not successful in expressing his love for Rosalind to her.
At the start of the play Orlando complains about the harsh treatment given to him by his brother, Oliver, and says that Oliver will not even give him the paltry sum of 1000 crowns left to him in their father's will. He is portrayed as exceptionally strong in both body and in his devotion to love. It is these qualities that make Rosalind fall for him as well.
After angering Oliver's crony Duke Frederick, Orlando flees his familiar surroundings to live in exile in the Forest of Arden. There, he is accepted into the circle of the usurped Duke Senior and is eventually united in marriage with Duke Senior's daughter, Rosalind. Actor Laurence Olivier played the character in a 1936 film with Elizabeth Bergner opposite him as Rosalind.
According to at least one legend, the character is the namesake for the city of Orlando, Florida.