11 / 18
'Some Like It Hot'
Playing a woman in 1959 took a whole lot more courage than it does nowadays. Jack Lemmon and ...
11 / 18
Playing a woman in 1959 took a whole lot more courage than it does nowadays. Jack Lemmon and ...
12 / 18
...Tony Curtis played two men on the run from gangsters! They did their best to hide in plain sight as part of an all-female traveling band.
13 / 18
The drama 'Dallas Buyers Club' tells the tale of an AIDS patient's fight against the American health care system and is the only film on this list that is not a comedy.
14 / 18
30 Seconds to Mars singer Jared Leto was awarded an Oscar for Best Supporting Role in 2014 for his performance as the transsexual "Rayon".
15 / 18
The film 'Tootsie' is not just a comedy, and despite its cross-dressing element it actually won several Oscars...
16 / 18
...and that was thanks to Dustin Hoffman's amazing performance!
17 / 18
When "Daniel's" ex-wife does not let him see his children any more, he hatches a cunning plan. He applies for a position as the children's nanny and transforms himself into 'Mrs. Doubtfire'...
18 / 18
It was, of course, Robin Williams hiding behind 'Mrs. Doubtfire's' old-fashioned wardrobe. The ugly clothes were worth it however, as Robin Williams was lauded for his performance as the unconventional nanny back in 1993.