In “Some Like It Hot,” two men, Jerry and Joe, narrowly escape a raid in the prohibition era and a day later witness the murder of the informants that gave the party away, much like the St. Valentine's Day Massacre. To escape Spats Columbo and the rest of his mobsters, they flee Chicago disguised as Daphne and Josephine and join an all-woman band. Along the way, they befriend Sugar Kane, with whom Joe falls in love. With the help of his cross-dressing friend, Joe tricks Sugar into thinking that he is the rich air to the Shell Oil Corporation and she falls for him as well. However, Spats catches up to them and they flee once again with Sugar and a confused, dirty old man in tow. Billy Wilder explores major dynamic changes in his main characters and hilarious coincidences to show the world is flawed and that nobody is perfect.
Wilder defies the thought that there is only one kind of perfect love with this gender-bending and racy farce, filled with crafty and clever sexual innuendos, unapologetic crudity, unrestricted love, sexy costuming for the well-endowed, bosomy Marilyn Monroe, an outrageous and steamy seduction scene aboard a yacht, and a mix of serious themes including abuse, alcoholism, unemployment, and murder, and parodies of sexual stereotypes such as transvestism, transsexuality, homosexuality, bisexuality, lesbianism, androgyny and impotence.
When Jerry and Joe first meet Sugar, they are both captivated by her charm, but Joe reminds Jerry that they are both “girls” and must not pursue her and risk giving their true identities away. Jerry reluctantly agrees saying “I’m a girl… I’m a girl… I’m a girl…” Later on in the movie, aging millionaire, Osgood Fielding III, courts Jerry, who is disguised as Daphne, inappropriately. Jerry tries to ward him off, but the rich old man is relentless. Eventually Jerry accepts his love due to the many gifts that Osgood offers him. Joe is baffled and tries to convince the smitten by money Jerry that that it would be impossible for them to marry asking “Why would a guy want to marry a guy?” Jerry answers happily: “Security” while dancing and shaking maracas.
It is plain to see that Joe is used to maintaining the “love ‘em and leave ‘em” mentality. However, when disguises himself as a girl, he learns just how damaging that mindset can be to the girls. When he befriends Sugar as Josephine, the opportunity to explore a non-sexual relationship with a woman opens up. Although he tries to woo her by providing a false identity, Joe gains a whole new perspective on Sugar’s hopes and dreams as she also strives to impress him. This gives Joe a heavy variety of new understandings and comprehensions, which begin to confront, and ultimately wash away the values that he has previously identified himself by. So when Joe and Jerry’s covers are blown by the mobsters and they must make a quick escape to evade the insidious seize of Spats and his men, Joe is faced with the difficult choice on how to leave Sugar. Before Sugar, Joe gave no thought to disappearing without a trace, but with Sugar, it is painful and grim. He tries to weaken the shock by sending her a diamond studded bracelet and calling her hotel room with a somewhat plausible excuse for his unanticipated disappearance. However, when Joe tries to flee, he is uncontrollably pulled back to the scene of a heart broken Sugar singing mournfully with the band. In order to comfort the dejected woman, he emerges from the shadows saying “No guy is worth it,” and kissing Sugar in front of