Billy Wilder's Some Like it Hot is Hollywood's most famous and most critically acclaimed movie that features men in drag. Despite having been made in the ultra-conservative 1950s, while the MPAA Code was still in place, Some Like it Hot blurs the boundaries between genders. Even if in jest, it refers, sometimes explicitly, to homosexuality. Marylyn Monroe's character, Sugar Kane, shares an on-stage kiss with whom everyone else presumes is a woman: Josephine or Joe.
When the movie begins, the lines between the genders isn't very stiffly drawn. Joe is a womanizing man's man who connives and cajoles his friend and roommate Jerry to attempt a gig 100 miles away. However, from the beginning, Jerry is portrayed as a more feminine character than Joe. Unlike Joe, he doesn't freely woo women, gamble, or insist on keeping his manliness for survival. Jerry is much more practical and frettish-- two traits that were commonly associated with femininity at the time. When the two men are presented an opportunity to survive, but as women, Jerry eagerly leaps for it while Joe insists on maintaining his masculine persona.
The movie ends with the main three on a boat driven by the Daphnephilic millionaire Oswald III. Jerry (as Daphne) comes up with increasingly outrageous (and false) reasons why Oswald and Daphne should not get married. Finally, in frustration, Jerry takes off his wig and declares "I'm a man!" The unperturbed Oswald simply replied "Nobody's perfect."
Despite this blurring of gender lines, Some Like it Hot simultaneously totes and parodies a patriarchal, marriage-centered societal ideology. Sugar, the main leading actress, is a combination of very stereotypical, sexualized female characteristics. Her walk is described by Jerry as being "like Jell-O on springs", and she even describes herself as not being very bright. At the end of the day, all Sugar really cares about is love-- and therefore, men. Despite being a mildly successful band singer, Sugar is instead like women in the kind of society idolized by screwball comedies: a mindless sexual object with purely domestic aspirations. Yet, like in most screwball comedies, she is placed on equal (and sometimes superior) romantic footing to her male counterpart.
Some Like it Hot is arguably progressive for its time. It's also arguably a reflection of the era in which it was made. It most definitely is simply one of the funniest movies ever made.