Pretty Woman (1990)

Replete with extreme wealth and suave good looks, Edward Lewis could seemingly have any woman he wants, a committed significant other needed on his arm at social events to further how he makes his money as a corporate raider, but since he focuses more on his corporate-raiding pursuits with his lawyer of 10 years and partner-in-crime Philip Stuckey than any woman, every significant other he's had in his life has felt neglected and eventually left him, the fact of which he is just realizing. In Beverly Hills, still in need of a woman on his arm as he and Philip work toward taking over a company owned by the increasingly insolvent James Morse, he decides, from a chance encounter, to hire Hollywood Boulevard hooker Vivian Ward as his escort for the week. It makes sense: a professional who would be committed to the work without having any relationship issues after the week is done. 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, must still look and act the part, with Edward, beyond giving her money, leaving her largely to her own devices to do so. She finds a somewhat-unlikely Henry Higgins in Barney Thompson, manager of the Beverly Wilshire Hotel where Edward is staying. Barney draws 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 to 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.