Billy Wilder's "Some Like it Hot" (1959)

This is a classic comedy from the late 1950's which opens with two friends (Jack Lemmon and Tony Curtis) who play in a jazz band in a speakeasy set up in a funeral home. This is during the heyday of Prohibition.   The police raid the speakeasy that night and so they are out of a job.  It is the middle of a snowy February in Chicago and in their desperation they decide to join a "girl's jazz band" on its way to gigs in Florida,  taking on female identities.  The conceit is, of course, the fact that they easily "pass" for females when clearly they do not.    

To make matters worse, when they go to pick up their car in order to head south to join the band, the garage where it is located is the site of the notorious St. Valentine's Day Massacre, in which one set of gangsters kill off a rival group of gangsters who are playing a poker game in the garage.  This surviving gang is headed by Spats Colombo (George Raft).  Curtis and Lemmon witness the massacre and when they are noticed as witnesses, they run for their lives.

Curtis and Lemmon in drag.

  Now their leaving town becomes even more imperative and their drag disguises serve as protective coloration.    They take the train instead with the all- girl's band in a Pullman car.  Their lead singer is none other than a woman named Sugar (Marilyn Monroe), who confides to them that she is unlucky in love and that what she really wants to do is marry a millionaire so that she can retire.

Marilyn Monroe

  At this juncture Tony Curtis starts to pursue Marilyn and to do so, pretends to be a millionaire with a yacht and a fake Cary Grant accent.  Meanwhile Jack Lemmon in drag ends up being the reluctant object of the determined attentions of a real millionaire, played by Joe E. Brown. 

These various facts allow the plots to dovetail and comic mayhem ensues.  Unfortunately for the fugitives, it is at this point that the hotel where they are staying is hosting a convention of "Friends of Italian Opera",  a thinly veiled mafia get together and the same Spats Colombo meets them in the elevator.  The guys are charmed too by the faux ladies but they (unlike anyone else in the story) somehow sense that they aren't ladies at all, but in fact are their fugitives. 

It was a very popular movie when it was released in 1959.    Men in drag have been a potent resource for comedy for generations.  Marilyn Monroe is shown in all her blonde voluptuousness.  That Tony Curtis's character is driven to absurd lengths of deception in order to seduce her, seems a favorite comic device of the 1950's and

1960's, and so have the so-called "buddy movies" featuring a comic duo, such as in the past Bob Hope and Bing Crosby,  Jerry Lewis and Dean Martin, and now Tony Curtis and Jack Lemmon. 

One of course can't help but reflect on the sad fate of Marilyn Monroe a scant three years later.  What was with her strange relationship with Joe DiMaggio and Arthur Miller?  How did her loveless childhood, uncertain patrimony, foster homes, and the abusive nature of Hollywood affect her?  She seems to have been medicated and psychoanalyzed to death, and at 36 she must have seen the approaching decline in the only thing that really sustained her in Hollywood:  her appearance.