This description of previous roles played by Tilda Swinton gives some insight into the choices made when casting her as Orlando. Swinton had previously played other roles as a male, including a turn as Mozart. The intertextual baggage of Swinton's star persona brings its own androgynous qualities that are fitting to the character of Orlando, especially when concerning his/her's contemplation of gender politics and the transition he/she under goes. Also Swinton's educational background in English Literature would suggest that she had a previous affinity with Woolf's novel.
Given Sally Potter's background in Dance and Performance Art it appears that she has taken advantage of the multitrack medium of film to pursue a personal interest as well as continuing with certain key themes from Woolf\'s novel. Woolf spans Orlando over four centuries through various historical periods in attempt to chart the development of British history and in particular depict a playful account of the evolution of literature. Likewise Sally Potter is keen to add another layer to this mapping of historical and cultural change by charting the evolution of music throughout the ages also.
This painting of the Great Frost (created, presumably, by the film's production designer Christopher Hobbs) was generated to assist Sally Potter with her visual realization of the novel. The Great Frost was a real historical event in 1608 which Virginia Woolf used as a setting for one of the many historical periods in the novel. The ironic depiction of this historical setting in the film - a sequence where the Muscovite Embassy visit England at a time when the River Thames is frozen - is that Orlando originally a british production eventually became a co-production with other countries, the first being the USSR, and that this sequence was in fact shot in Russia.