“Orlando” draws from a novel that has generated considerable discussion, and it handles complex themes with surprising effectiveness. Virginia Woolf’s “Orlando” is an intriguing and often debated work by an author whose own life was marked by hardship: childhood sexual abuse, bouts of depression, lifelong existential questioning, and bisexuality. The novel emerged from the relationship between Woolf and Victoria Sackville West, a woman who maintained an unconventional marriage that allowed her to explore relationships with other women. It’s possible that Victoria or even Woolf herself occasionally considered or imagined undergoing a sex change; regardless, “Orlando” seems to be among the earliest literary explorations of transsexuality. The film largely adapts Woolf's narrative, presenting a story about Lord Orlando, a young androgynous English nobleman from the Elizabethan court who captures the attention of the queen. She bestows upon him the gifts of eternal youth and immortality, which he then experiences firsthand! (Although the drawbacks of this gift are never explored.) As such, Orlando journeys through centuries without aging, experiencing love and travel in various locations. He falls into a deep sleep from which he eventually awakens to find himself transformed into a woman, spending the next two hundred years demonstrating that not only has he lived forever but also changed gender. The story concludes in contemporary times. The film significantly advanced Tilda Swinton’s career; she had already cultivated an androgynous image, perhaps influenced by growing up with several male brothers. Her performance is captivating, and she carries the movie with a remarkable portrayal. John Wood and Quentin Crisp also deliver noteworthy performances. Visually, the cinematography is striking and beautiful, and the film maintains a deliberate pace that might require some patience from viewers but ultimately holds their interest. Primarily filmed in Britain, it utilizes stately homes to create its settings, and the costumes are meticulously designed for each historical period.

Source on TMDB