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Here is a list of the best cross-dressing movies that can include a man dressed as a woman or a woman dressed as a man. Genre-wise, this list includes both dramas and comedies and even a few thrillers. Cross-dressing has been a staple of storytelling since ancient Greece. At times, it was even required by law as women were sometimes prohibited from working as actors. While some may consider crossdressing and transvestites as something that only belongs in comedy, that is far from the truth. Many of these films are dramas, and movies like "Psycho" are all out horrors.
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The Best Cross-Dressing Movies

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Top 50 drag queen / transgender / crossdress movies that are not so easy to spot

PG 65 min Drama. A psychiatrist tells the stories of a transvestite Glen or Glenda and a pseudohermaphrodite Alan or Anne. Director: Edward D. Wood Jr.
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