Diversity in Media Representation: LGBTQ: Cross-dressing
a character engages in the practice of wearing clothing stereotypical to a gender other than the character's predominantly-identified gender
"I'm a Girl", Some Like It Hot
Joe/Josephine (Tony Curtis) reminds Jerry/Daphne (Jack Lemmon) to pretend to be a girl after seeing him talk with Sugar (Marilyn Monroe).
"Rose Tint My World", The Rocky Horror Picture Show
After being frozen by Dr. Frank N. Turner (Tim Curry), Columbia (Nell Campbell), Rocky (Peter Hinwood), Brad (Barry Bostwick), and Janet (Susan Sarandon) reflect on their experiences by singing "Rose Tint My World."
"You're a Boy", Some Like It Hot
Jerry/Daphne (Jack Lemmon) tells Joe/Josephine (Tony Curtis) that they got engaged to Osgood (Joe E. Brown), and Sugar (Marilyn Monroe) announces her engagement to Shell Oil Junior (Tony Curtis)
Closing Sequence, Some Like It Hot
Joe/Josephine (Tony Curtis) and Jerry/Daphne (Jack Lemmon) escape the hotel with Osgood (Joe E. Brown), and Sugar (Marilyn Monroe) runs to join them.
Cross-dressing, Bessie
Bessie (Queen Latifah) travels the country with her mentor, Ma Rainey (Mo'Nique). After Bessie's first performance, Ma Rainey performs, cross-dressed as a man
Dr. Frank N. Furter Sings "Sweet Transvestite", The Rocky Horror Picture Show
Couple Brad (Barry Bostwick) and Janet (Susan Sarandon) meet Dr. Frank N. Furter (Tim Curry) who sings "Sweet Transvestite."
Josephine and Daphne, Some Like It Hot
Joe (Tony Curtis) and Daphne (Jack Lemmon) disguise themselves as women named Josephine and Daphne to join an all-female band headed to Miami.