"Joe-Josephine was one of his most risky and fulfilled roles," said Insdorf, author of "Francois Truffaut," "Indelible Shadows: Film and the Holocaust" and "Double Lives, Second Chances: The Cinema of Krzysztof Kieslowski."
"It's not just that his character Joe pretends to be Josephine. When he is drawn to Marilyn Monroe's Sugar on the beach, he adopts a second disguise, that of a millionaire snob who talks like none other than Cary Grant.
"When they meet on the beach, both are playing roles. Sugar claims to be a society girl, because each thinks it's what the other wants to hear. We see that even when Joe is in a male disguise, he adopts a female pose, namely the reticent object of interest rather than the aggressor. It's Sugar who must ask to see him again, while he acts like she has intruded on him."
Insdorf described how the seduction scene on the yacht takes these reversals to an extreme.
"Joe plays effeminate as Sugar plies him with Champagne, turns on the romantic music and dims the lights," she said. "Sugar is the masculine to Joe's feminine. Talk about layers! Monroe's character is attempting to cure a phony millionaire's phony impotence!"
Audiences of the time loved the way Curtis and Lemmon impersonated women, said Insdorf, perhaps because there was something nonthreatening in the heterosexual "drag" characters of "Some Like It Hot."
"And now we can appreciate all the more Curtis' courage, craft and charisma," she said.