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1
How can Some Like it Hot be characterized as a “comedy of redemption?”
Through his persona as Daphne and his subsequent romantic relationship with Osgood, Jerry comes to a fuller appreciation and understanding of the objectification of women as sex objects. While his realization is not especially explicit, Jerry begins his journey in drag as nothing more than a leering predator. Once they get to Florida, however, and Jerry is subjected to the predatory ways of men, he begins to see just how hard it is for a woman. He laments the unwanted male attention to Joe by saying, "I'm not even pretty." As Joe assures him, "They don't care. Just so long as you're wearing a skirt. It's like waving a red flag in front of a bull." To this, Jerry responds, "Really. Well I'm sick of being the flag. I want to be a bull again." It's not quite so easy, however, and soon Jerry comes to appreciate his life as a woman, taking his role so seriously that he accepts Osgood's proposal of marriage. This event also teaches Jerry a lesson, that women are conditioned to become dependent upon men. By switching roles and becoming the receiver of gifts and marriage proposals, Jerry realizes the complex structures that dictate the dynamics between men and women. In this way, he undergoes a kind of conversion, because he has to see the world from a female perspective. Joe too, in posing as Josephine and hearing firsthand from Sugar just what is so frustrating about navigating the world of men, comes to see his life from a woman's perspective, and seeks to amend his behavior to meet her standards. While neither Jerry nor Joe are explicitly redeemed by the end—it's more complicated than that—their time posing as women teaches them some monumental lessons about sex and gender.
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2
How is the central premise an instance of dramatic irony?
The main comedic premise that determines the entire film is that Joe and Jerry, two very masculine men are convincingly able to pose as "Josephine" and "Daphne" and join an all-girl band. Dramatic irony occurs when the audience knows something that a character does not. In this case, while the viewer knows that "Daphne" and "Josephine" are actually men, the women in the band, and most people that the two "girls" encounter, do not realize. This makes for an especially exciting comedic tension. Sugar and the rest of the girls in the band treat "Josephine" and "Daphne" like sisters, confiding in them, snuggling up with them in bed, girlishly laughing with them. The humor stems from the fact that the audience knows that if the girls knew "Josephine" and "Daphne"'s actual sex, they would not behave in the same manner.
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3
How does the treatment of gender and sexuality in Some Like it Hot challenge conventional assumptions?
The entire point of men dressing in drag in most film comedies is to remove them from the norm and place them into a world that is apart from the conventional societal expectation. It is a way for the characters to find themselves in an unexpected situation, so that narrative expectations and dramatic turns can occur. Many cross-dressing films tempt with homosexual subtexts within the fantasy world, but almost always insist upon a clearly marked return to heterosexual normalcy at the end. Some Like it Hot is unique in that the relationship between Daphne and Osgood is left complicated, even after the revelation that "Daphne" is "Jerry." The audience's assumptions are challenged directly in the film’s final famous closing lines in which Osgood responds to Jerry’s revelation with a shrug and the simple line, "Nobody's perfect." The comedic and ambiguous final note leaves the audience wondering if perhaps Osgood and Jerry will attempt to stay together, if their love is enough to overcome their presumed heterosexuality. It gives a more complex, while still light-hearted, picture of homosexual desire that sets it apart from other films that prefer to make drag performance simply a passing joke or a sight gag.
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4
What is comedic about "Junior" and Sugar's date on the yacht?
There are several comedic elements to this scene in the film. For one, Joe as "Junior," knowing that Sugar does not want to date a guy who comes on too strong and then leaves her flat, plays hard to get, pretending that a tragic event has left him cold to the touch of a woman. When we first met Joe in the beginning of the film, he was leering at some chorus girls at the speakeasy, and playing love games with the secretary at his agency. Now, as "Junior," a lockjawed oil tycoon, he feigns impotence in order to entice Sugar to seduce him and fall even more deeply in love with him. Just the image of a heterosexual man saying that he feels no desire for the iconically desirable Marilyn Monroe strikes a comic note, by itself. Additionally, both Joe and Sugar are pretending to be upper crust blue-blooded Americans with trust funds, but neither knows much about those worlds, and they know even less about the ocean and nautical topics. When Sugar asks which side is port and starboard, Joe tells her that it depends on how one looks at it, rather than giving an authoritative answer. Neither can identify the swordfish on the wall, and Joe even says it's a member of the "herring" family. The duo's clumsy pretensions out on the boat are charming and endearing, as the audience knows that neither one of them feels especially at home on a giant yacht.
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5
What are some scenes in which director Billy Wilder bypasses reality in order to heighten the comedy?
For one, the sight gag of Tony Curtis and Jack Lemmon in drag strikes a very comic tone. As they get more deeply embroiled in the film, it gets all the funnier. Several moments in the film slip out of any semblance of realism in order to maximize the comedy. First, on the train, the girls in Sweet Sue's band pile into "Daphne"'s bunk at the mere mention of a party. There are so many girls and they chatter in such high-pitched exuberance, that it's somewhat hard to believe as a plausible scenario, but it sure is funny. Then later, when the band arrives in Florida, we see immediately that Sugar's assessment of Florida as a place that bespectacled millionaires "flocked" to in the winter is cartoonishly correct. On the porch sit almost a dozen old millionaires, all in glasses and hats. They all read the paper, rocking in complete unison, taking off their glasses, and ogling at the girls in the band at the exact same time. The moment is choreographed as though it were a musical number, flipping out of strict realism and into a more playful relationship to reality. Additionally, the choreography of how and how quickly Joe and Jerry switch in between drag and their street clothes at the end when they are trying to elude the gangsters is completely outside the realm of realism, but it makes for a suspenseful chase.