Victor Victoria (1982): With exceptions (The Crying Game, The World According to Garp, etc.), male cross-dressing is at least intended, however successfully, as an easy laugh. (Or in Jack Lemmon’s and Dustin Hoffman’s cases, an actual good one.) For whatever reason, hilarity doesn’t automatically arise when the cross-dressing goes the other way. Even the sight of Julie Andrews as a down-on-her-luck actress pretending to be a man (then later pretending to be a man pretending to be a woman) is funny because of the farcical situation behind it, not because Andrews in a tux is on-its-face amusing. Her co-star Robert Preston in a dress, on the other hand ...
The Year of Living Dangerously (1982): For his docudrama on the overthrow of the Indonesian president Sukarno in 1965 as seen by Westerners, director Peter Weir hired diminutive Linda Hunt to play Mel Gibson’s male dwarf photographer. Hunt won an Oscar, a trophy nearly, but not quite, awarded to Cate Blanchett when, as a bizarrely credible Bob Dylan, she pulled the same stunt in I’m Not There.
Yentl (1983): Bear in mind that Barbra Streisand’s musical, in which she tries to pass herself off as a boy in order to attend Yeshiva, sports much the same premise as one of the era’s less esteemed pictures, Just One of the Guys.
Twelfth Night (1996): Shakespeare employed the device of a woman successfully passing herself off as the less fair gender more than once—a device, admittedly, cleverly borrowed by Shakespeare in Love . Too bad there are no decent film versions of this mad comedy, where one woman’s cross-dressing deception leads to many broken hearts.
The Associate (1996): In which Whoopi Goldberg one-ups Andrews, Streisand, Blanchett, et al. and not only cross-dresses but cross-dresses into a white man. Hilarity, presumably, ensues.
Albert Nobbs (2011): What Hunt did was technically impressive, but what attracts people to the film where Glenn Close plays a woman passing herself off as a man—as it did with Hilary Swank in Boys Don’t Cry—is the added element of the pain of gender reassignment, of having to exist under an elaborate lie. Of course, Close isn’t going to win that Oscar.
It was 1982 when Glenn Close first played Albert Nobbs, a woman in 19th century Ireland who, thanks to a short ’do and vaguely androgynous features, has passed herself off as a man, in order to reap the then-vocational benefits of the gender.
Neil Barsky’s "Koch" Keeps It Light