Little Lord Fauntleroy (1921): You know what? Kids are too often trusted to play kids. Frances Hodgson Burnett’s oft-filmed tale of a spoiled little shit usually gets cast with spoiled little shits (like Ricky Schroeder). But this silent version borrowed a move from the stage version of Peter Pan, casting 29-year-old Mary Pickford as the dandy scion (as well as his mother).
Sex Change (1977): In Transamerica, the filmmakers had a decision to make: Should their lead, a MTF transperson, be played in her pre-op state by a man or a woman? They went with Felicity Huffman, who scored an Oscar nomination for spending most of the film as an effeminate man. And the makers of this Spanish drama, about a 17-year-old who dispenses with his unwanted member, went with young hottie Victoria Abril.
The Year of Living Dangerously (1982): When men play the opposite sex, or merely don their clothes, the intent is usually to attract laughs. When women do it, they tend to take it seriously, and are thus taken seriously. Acting opposite a noted racist, diminutive Linda Hunt scored an Oscar for playing a photographer in boiling-over Indonesia, which required her to pass herself off as not only male but half-Chinese.
A Man Like Eva (1984): Two years after his drug-fueled death, director Rainer Werner Fassbinder received an appropriately outré homage, with Eva Mattes, one of his regular actresses, playing a Fassbinder-esque director who throws a Fassbinder-esque tantrum while living with the cast and crew of his latest movie.
Orlando (1992): With features so androgynous a once joked-about David Bowie biopic can only be so far off, Tilda Swinton broke into the mainstream playing Virginia Woolf’s ageless, gender-switching hero(ine), which required her to be slightly unconvincing as both an Elizabethan man and a 19th-century lady. Meanwhile, Quentin Crisp does a mean Queen Elizabeth.
I’m Not There (2007): Cate Blanchett’s Oscar was a result of her Katherine Hepburn impersonation, but her Bob Dylan is even more impressive. Party trick!
Six Long-Running Film Franchises