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Picture of a movie: Miss Congeniality
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Miss Congeniality

2000
Undercover F.B.I. Agent Gracie Hart shows no signs of having any femininity in her demeanor or appearance. Generally a bright and capable Agent, she is in trouble at work when she makes an error in judgment in a case which results in a near disaster. As such, one of her by-the-books colleagues, Eric Matthews, who has never shown any inclination of thinking outside the box, is assigned to lead the high profile case of a terrorist coined The Citizen instead of her, while she is facing possible disciplinary action. Gracie pieces together the evidence to determine that The Citizen's next target will be the Miss United States beauty pageant. The pageant represents everything that Gracie abhors. Despite Gracie's mannish demeanor, Eric, with no other undercover female Agent remotely fitting the demographic, assigns her to go undercover as a pageant contestant to see if she can flush out The Citizen, who is perhaps one of the other contestants. Although the pageant administration, led by former winner Cathy Morningside and long time host Stan Fields, provide the F.B.I. with access to the pageant, Cathy in particular is less than thrilled to have a non-credible Gracie posing as a contestant, which she feels will ruin the pageant. The F.B.I. enlist the assistance of former pageant contestant coach Victor Melling, who is facing his own disgrace associated with the pageant, to do the nearly impossible task of transforming Gracie, not only into a woman, but a credible beauty pageant contestant. As Gracie proceeds in the transformation, she gets to know the other contestants, not only as potential criminals, but also as real people. She also discovers that another sinister element is present at the pageant. She will do whatever it takes to quash that element and protect her new friends, namely the other innocent contestants. But now displaying some femininity, Gracie begins to have more womanly feelings, and in turn, attracts the attention of men, one in particular about whom she is happy.
Picture of a movie: Pretty Woman
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Pretty Woman

1990
Because of his extreme wealth and suave good looks, Edward Lewis could seemingly have any woman he wants, that committed significant other which he needs on his arm at social events to further how he makes his money as a corporate raider. However, he focuses more on his corporate raiding pursuits with his partner in crime, Philip Stuckey, his lawyer of ten years, than those women, with every significant other he's had in his life feeling neglected and eventually leaving him, this fact about which he is just coming to the realization. In Beverly Hills, Edward, in needing that woman on his arms as he and Philip work toward taking over the company owned by the increasingly insolvent James Morse, decides, based on a chance encounter, to hire Hollywood Boulevard hooker Vivian Ward as his escort for the week 24/7. He does so because he wants to have a professional who would be committed to the work, yet not have any commitments to her after the week is over. Beyond their chance encounter, he also makes this decision because she surprises him about how unhookerish she is in certain respects. Vivian, relatively new to Los Angeles and the business, still has to look and act the part, with Edward, beyond giving her money, leaving her largely to her own devices to do so. So she gets a somewhat unlikely Henry Higgins in Barney Thompson, the manager of the Beverly Wilshire Hotel where Edward is staying. Barney has to draw that fine line of keeping the hotel's upscale clients happy, while maintaining the posh decorum of the upper class, which does not include people coming into the hotel looking for rooms with hourly rates. As Barney and his associates are able to transform Vivian into a Cinderella, the questions become whether Vivian can go back to her Hollywood Boulevard life and whether she does have her Prince Charming beyond this week in the form of Edward or anyone else who truly does see her as Cinderella as opposed to a Hollywood Boulevard streetwalker.