Virginia Woolf's biography touches on her marriage to Leonard Woolf as well as her inclusion in the Bloomsbury Circle. Further research shows that the group was surprisingly progressive in its views on sexuality, with many of its members involved in various affairs with members of their own sex. Woolf herself was involved with Vita Sackville-West, and in fact wrote Orlando as a sort of love letter to Vita, basing the character on her.
The choice to cast a female actress in the role of Orlando throughout the film and his change from male to female is an important aspect of the gender fluidity inherent in the story. This connects not only to Virginia Woolf's feminist writings but also to the fact that Orlando is based on Virginia's lover, Vita Sackville-West.
Actor Quentin Crisp in the role of Queen Elizabeth. Much like casting a female actor to play the initially male character of Orlando, the choice to use a male actor to portray the Queen is a deliberate play on gender roles. There is also a strong sense of intertextuality at play in casting Crisp, as he was England's most famous drag queen.
Female-Orlando with her next love, Shelmerdine. The inclusion of a female lover for male-Orlando and a male lover for female-Orlando is important as it shows the fluidity not only of gender but of sexuality. Orlando is a loving and passionate character, regardless of which gender the character or the lovers are.