Who wears the pants? These women all did, on screens big and small, anyway -- and awards voters loved them for it.
Linda Hunt: OK, shes not the most feminine in her everyday life, but still, Hunt was an Oscar winning trailblazer when she played a Chinese dwarf in The Year of Living Dangerously. Even more amazingly, Mel didnt beat her up.
Tilda Swinton: As the eponymous Orlando, Swinton changes sex midway through the film, but for that first half shes all man and nothing short of luminous.
Cate Blanchett: Blanchett was one of five Bob Dylans in Im Not There -- but she was the only Bob whose performance got the Academys nod.
Hilary Swank: Swank touched the world as tragic transman Brandon Teena in Boys Dont Cry and took home the Oscar -- noting a trend?
Felicity Huffman: Some might call this one a stretch for this list. After all, in Transamerica, Huffmans Bree lived her life as a woman. But lipstick aside, Bree still had some boy parts (thanks to very realisitic prosthetics) and if you still pee standing up, you make this cut.
Meryl Streep: At the top of Angels in America, who amongst you recognized Meryl Streep as The Rabbi? Yes, shes known for disappearing into her roles, but this was a stretch even for her (Meryl as Jewish, really?). Emmy thought so, too.
Vanessa Redgrave: Like Huffman above, Redgrave played a man who becomes a woman. But in Second Serve, as tennis legend Renne Richards and the pre-op Richard Radley, Redgrave, did it 20 years earlier.
Miriam Shor: OK, sure, John Cameron Mitchell got the Farrah wig in Hedwig and the Angry Inch, but Shor, as Yitzhak, got the facial hair and the drums!
Nancy Cartwright: In what must be a gender reversal record, Cartwright has spent 21 years voicing Americas most famous 10-year-old boy, Bart Simpson.
Honorable mention: Julie Andrews, Barbra Streisand, Katherine Hepburn, and Gwyneth Paltrow. Yes, we're cheating. Technically, they werent playing men. They were women living as men for plot devices and Oscar glory. But even though none of them were believably male for even a frame of film, we cant ignore Victor/Victoria, Yentl, Sylvia Scarlett and Shakespeare in Love.