Actors and actresses have enjoyed playing the opposite sex in movies. Who can not chuckle to remember Robin Williams as “Mrs. Doubtfire” or Dustin Hoffman as “Tootsie.”
Women have been remarkably brilliant as men. From old screen actress Mary Martin to Cathy Rigby, Peter Pan has traditionally been played by a woman. The latest is Allison Williams, who’ll don the green tights and pointy hat for NBC’s live broadcast of PeterPan on December 4, 2016.
Linda Hunt, ‘The Year of Living Dangerously’
Hunt’s performance as photographer Billy Kwan rightfully landed her the Best Supporting Actress Oscar in 1984. She was not just convincing — Billy fully existed as Billy.
Hilary Swank, ‘Boys Don’t Cry’
Swank was heartbreaking as budding transman Brandon Teena in this fact-based movie. The story ended in tears, though it did help Swank win the 2000 Oscar for Best Actress and launched her career.
Glenn Close and Janet McTeer, ‘Albert Nobbs’
Playing a woman who dressed as a man to get better work was a labor of love for Close, who spent 30 years on getting this to the screen. Her grim-faced Albert is rather uptight (and sounds oddly like Linda Hunt) while McTeer’s cross-dresser, Hubert, is looser and freer — and even gets the ladies.
Cate Blanchett, ‘I’m Not There’
Blanchett turns up as a handsome rascally dude in Todd Haynes’ arty Bob Dylan biopic. Oh wait, she’s actually meant to be Dylan? Oddly, it kinda works.
Julie Andrews, ‘Victor/Victoria’
Andrews plays a woman who dresses as a man who dresses as a woman in Blake Edwards’ classic movie musical. Sleek in a 1930s way — acting butch just seems easier with greased-back short hair — her Victor is cute enough to seduce James Garner’s otherwise straight character.
Barbra Streisand, ‘Yentl’
Babs’ title character passes off as a boy so she can study at a yeshiva. Binding her breasts isn’t such a high price to pay, until Yentl meets Mandy Patinkin, then at the height of his hunky glory. What’s a nice cross-dressing Jewish girl to do?
Mariah Carey, ‘Obsessed’
The close-up of a dazed-looking Carey with scruff Scotch-taped to her/his chin is priceless. And that’s just the beginning of this hilarious music video in which one of the womanliest female singers ever dons male garb to stalk herself. She wouldn’t fool your blind Aunt Mary but who cares? This is grand camp!
Tatiana Maslany, ‘Orphan Black’