5. Victoria (Victor/Victoria)
Victor/Victoria is a film in which Julie Andrews plays a woman pretending to be a man who is pretending to be a woman...Got that? Victoria is a struggling singer in 1930's Paris who finds work as a female impersonator in a cabaret venue. An already complicated situation gets even more complicated when straight gangster King Marchand (James Garner) finds himself falling for "Victor" much to his confusion. It's all a far cry from The Sound Of Music!
6. Brandon Teena (Boys Don't Cry)
While cross-dressing in the movies tends to appear most often in the comedy/musical side of the spectrum, Boys Don't Cry is a rather more serious affair. Hilary Swank won an Oscar for her role in this true-story of a young woman living her life as a man in rural Nebraska. Teena was raped and murdered men that had once been her friends when they discovered his secret. Swank was so convincing in the role, with her cropped hair and masculine demeanour that many people were shocked at how feminine a presence she was as she collected her award in 1999.