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*** BAKER'S DOZEN - Actors who have played characters of the opposite sex ***


excluding drag, trans characters

1. Linda Hunt - The Year of Living Dangerously (1982)

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1. Linda Hunt - The Year of Living Dangerously (1982)
2. Mulan (1998)
3. Yentl (1983)
4. Mrs. Doubtfire (1993)
5. Suspiria (2018)
6. Cate Blanchett - I'm Not There (2007)
7. Gwyneth Paltrow - Shakespeare in Love (1998)
8. Tyler Perry - Madea movies
9. Tilda Swinton - Constantine (2005)

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1. Linda Hunt - The Year of Living Dangerously (1982)
2. Mulan (1998)
3. Yentl (1983)
4. Mrs. Doubtfire (1993)
5. Suspiria (2018)
6. Cate Blanchett - I'm Not There (2007)
7. Gwyneth Paltrow - Shakespeare in Love (1998)
8. Tyler Perry - Madea movies
9. Tilda Swinton - Constantine (2005)
10. Coming to America (1988)

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1. Linda Hunt - The Year of Living Dangerously (1982)
2. Mulan (1998)
3. Yentl (1983)
4. Mrs. Doubtfire (1993)
5. Suspiria (2018)
6. Cate Blanchett - I'm Not There (2007)
7. Gwyneth Paltrow - Shakespeare in Love (1998)
8. Tyler Perry - Madea movies
9. Tilda Swinton - Constantine (2005)
10. Coming to America (1988)
11. John Travolta/Divine - Hairspray (2007, 1988)

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Hillary Swank - Boys Don't Cry
Wayans Brothers - White Chicks

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I don't think either would qualify because they weren't playing a character of a different gender, they were playing characters of their actual gender who were pretending to be a different sex. In other words Tyler Perry is playing a woman in the Madea movies but the Wayans brothers were playing men who had to pretend to be women.

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So the Gwyneth Paltrow entry shouldn't be included either. She played a woman who pretended to be a man so she could get into the theater company. And Robin Williams was not playing a woman in Mrs. Doubtfire either.

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Yeah that's true too! This one has thrown everyone off and I think we need the OP to rule on all of them.

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Divine (Rosie Perez) - Lust in the Dust (1984)

Not sure of the count here.

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Some number between 2 and 13 : Alec Guinness as Lady Agatha D'Ascoyne in 'Kind Hearts and Coronets (1949)'

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