Orlando is the youngest son of the deceased Sir Rowland de Boys and a brother to the nasty tyrant Oliver. He is brave, chivalrous, tender, modest, smart, strong, handsome and beloved by all. The first time we meet Orlando, he’s fired up and says he’s ready to “ mutiny” against his big bro. His father has died and he’s been left penniless because of the system of primogeniture, which says that oldest sons get to inherit all of their fathers’ wealth while younger sons, like Orlando, get zilch.
Not only did Orlando get shafted in his dad’s will, he is also treated like dirt by his older brother, Oliver, who is supposed to be taking care of him: My father charged you in his will to give me good education: you have trained me like a peasant, obscuring and hiding from me all gentleman-like qualities. He resents the harsh treatment he receives at Oliver’s hands and complains that Oliver neglects 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. Orlando knows he’s angry, but here, he doesn’t know quite know what to do about it so he vents his frustration by running out and challenging Charles, the court wrestler, to a match. Orlando is the underdog every audience roots for, and miraculously he wins the match, even though Charles has a reputation as a bone crusher. Once he meets the luscious Rosalind, he falls head-over-heels in love. Like Romeo, Orlando responds to this new flood of passion by being a romantic drama queen.
He litters the Forest of Arden with sappy love poetry about Rosalind that he tags up on all the trees. Here’s an example, From the east to western Ind, No jewel is like Rosalind. Her worth, being mounted on the wind, Through all the world bears Rosalind. Orlando seems sincere, but this is also really bad poetry. Jaques even begs him to “ mar no more trees with writing love-songs in their barks”. He has plenty of spirit, not only does he beat up Charles in the wrestling match, he also fights a ferocious lion and saves his brother’s life.