An expert mixture of comedy, tension, sex, and romance

Rating: 10/10 (27 November 2019)

This movie is about as pure entertainment as movies can get. It's an expert mixture of comedy, tension, sex, and romance that creates such a complete package of good times that Hollywood has very rarely come close to matching. Working with I.A.L. Diamond for the second time after Love in the Afternoon, Billy Wilder crafted an essentially perfect film.
Set during Prohibition, we follow two jazz musicians after they witness a gangland murder and try to run for their lives. They're broke and can't even pay to get to a regular job 100 miles from Chicago much less fund an escape from the mob, so they do the only logical thing. They dress up like women and join an all-female band headed to Florida for three weeks. The two have been so consumed with bare survival in the winter of Chicago where they could only ever find unsteady work, that romance has been a secondary objective for a long time. Suddenly thrown into a train car with a dozen beautiful women including Sugar Kane (played perfectly by Marilyn Monroe), the two don't need to worry about feeding themselves or the back rent on their apartment or the coats they lost in a bet at a dog race.
Jerry, played by Jack Lemmon, embraces his femininity fully while also embracing the potential for sexual escapades. Joe, played by Tony Curtis, is a bit more forward thinking and knows that if they give away the game they'll be off the train and ready to freeze to death in the winter cold. Jerry sees their escape as an excuse to have fun, but since none of the other women on the train are suspicious of them, they treat the two like any other girl, ruining Jerry's attempt to have a surprise party with Sugar Kane by piling into his single berth in a display of absurdism that still feels completely natural in the film.
Two romances develop in the film. The first is between Joe and Sugar. It was Jerry who originally tried to make a lustful move towards the innocently sensual Sugar, but it's Joe who makes a concerted effort to win her heart. He's a man in a disguise who takes up another disguise (as a millionaire) while she is a woman who professes a need for a millionaire but also admits that she can't help herself around saxophone players (which Joe is). They're both lying about who they are to the other. Sugar is lying to both herself and to Joe's alter ego, Junior, about what she wants while Joe is lying to Sugar about who he is. The mutual lies end up canceling each other out in a way.
Jerry gets the second romance, this one with a real millionaire, Osgood Fielding III (played wonderfully by Joe E. Brown). He's a serial husband looking for his next wife (either eighth or ninth, only his mother keeps an accurate count), and he's smitten by Daphne, Jerry's alter-ego. Joe ends up bullying Jerry into playacting for Fielding in order to help Joe woo Sugar. The dual scene of Joe's reversed seduction of Sugar and the night out that Fielding and Jerry share is a marvelous display of contrasts. Joe is playing an impotent (maybe homosexual) rich dandy who needs Sugar Kane's feminine wiles to bring him back to life, so to speak. She tries with all of her innocently sexual energy. At the same time, Jerry and Fielding are dancing in a Cuban nightclub, Jerry accidentally leading at times while they grow closer in synch to the point where they can perfectly transfer a rose stem from one mouth to the other. It's a perfect mesh of comedic visuals with narrative push, driving the absurd romances on both sides forward.
The action of the film comes to a head when the gangsters from Chicago coincidentally have a get together with mobs from across the country in the same Florida hotel. The slapstick nature of two men dressed in drag running from gangsters reaches its peak here, embracing the absurdity with both arms fully. The resolution to the two romances is rather perfect as well. Joe and Sugar shedding their mutual deceit and falling into each other's arms in the back of Fielding's boat while Fielding dismisses all of Daphne's flaws as acceptable, even the fact that Daphne is actually Jerry.
Never has Wilder's common motif of masks and deception been more explicit than in Some Like it Hot (though The Major and the Minor comes close). He uses it to great comedic effect, crafting one of Hollywood's great comedies that feels as fresh in 2019 as it surely did in 1959.