Jack N Jill (1954)

Forgot to post about Jack N Jill featuring a very young and slender Dolphy as Gorio/Glory, a gender bending role which nearly every comedian afterwards would mimic and setting the caricature of the comedic gay character. Also gender bending the other way is Lolita Rodriguez (Benita, Gorio's sister), who to make money for the family pretends to be a guy to take on work as a driver. But, since she dresses like a girl in her off time, her gender bending is understood as a means to support the family, while Gorio needs to be "trained" out of his flirting ways.

The verbal cattiness flies fast throughout the film. As Benita find herself falling in love with the young rich gigalo she drives for. In the end, the message goes, a woman just needs to find the right man to make her a real woman, as well as make Glory a real man.