One of the golden rules in comedy is that men dressed in women’s clothing are universally funny. I don’t know why this is but it is the premise of the humour in Some Like It Hot. Unlike most other films that feature men dressed in drag, this is not just a one joke comedy, and is one of the funniest films ever made. After Tony Curtis and Jack Lemmon witness a gangland shooting, they disguise themselves as female musicians to get away from the gangsters.
Jack Lemmon is hilarious in this movie as Gerald/Daphne, and the closing line by his/her fiancé when it is revealed that Daphne is a bloke, is one of the funniest in movie history.
One of the things that I found interesting was the casting of Raft as Spats. In real life Raft was a low-level hoodlum before he became an actor in the late 20s, and rose to prominence in the original Scarface. One of the in-jokes that I found funny was when Spats chides a rival gangster who is constantly tossing a coin, something that Raft’s character did in Scarface. In another scene he picks up a grapefruit and looks as though he is going to squish it into someone’s face ala Jimmy Cagney in The Public Enemy.