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[[WhoopiGoldberg Laurel Ayers]] is a businesswoman trying to pave a way for herself on Wall Street, a society dominated by [[ScrewTheRulesIHaveMoney wealthy]] white men. Tired of receiving no credit for her work, Laurel quits her job and attempts to develop her own company. Unfortunately none of Laurel’s potential clients take her seriously. Desperate to have her ideas heard, Laurel invents an elusive business partner named Robert Cutty. By pretending all of her own ideas are actually that of Mr. Cutty, Laurel creates a successful investment firm and creates a celebrity out of the mysterious businessman.

Laurel’s plan hits a snag when it becomes necessary for the fictional Mr. Cutty to make a physical appearance. With the help of her secretary Sally Dugan, [[SweetPollyOliver Laurel disguises herself in prosthetics]] [[WhiteLikeMe as the elderly white businessman]]. Despite a series of mishaps, Laurel manages to pull off her masquerade for a night without being discovered. Trouble mounts as Laurel’s former business partner Frank becomes fixated on ruining her success. Meanwhile dozens of high-profile people want a piece of Cutty including a [[IntrepidReporter nosy gossip columnist]] and a stock broker who has a reputation for [[ReallyGetsAround sleeping her way to the top]]. As everything spirals out of control, Laurel must figure out how to get rid of Cutty and stand on her own two feet.
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!! This film provides examples of:
* AllMenArePerverts: The fact that an important lunch meeting is held at a strip club makes it pretty obvious.
* AmbitionIsEvil: Averted. If it weren’t for Laurel’s ambition to implement her own ideas, Syntonex would have gone bankrupt.
* ArentYouGoingToRavishMe: Camille’s reaction to Cutty’s disinterest in her.
* BlackBraAndPanties: Camille wears it well.
* BuxomIsBetter: Sandy, a businesswoman at Manchester, tells Laurel that she’s considering getting breast implants because it helps in business. She suggests that Laurel flash a little more cleavage in the office if she wants businessmen to listen to her.
* TheCameo: Golf player Johnny Miller and DonaldTrump.
* CigarChomper: Donald Fallon is one. The employees at Syntonex assume Cutty to be one as well and send him a box of cigars in thanks for saving their company.
* CorruptCorporateExecutive / ThereAreNoGoodExecutives: Played straight. Even [[spoiler: Fallon]] whom Laurel trusted with most of her business ended up selling her out in favor of doing business with Cutty only.
** Averted with Aesop Franklin. He might be socially inept but he is a very decent businessman.
* DoubleStandard: Laurel's biggest struggle is to overcome double standards in the workplace. Laurel quits her original job because Frank, the employee she trained, received the promotion she had been eyeing simply because the company didn't want a woman in the position.
* DragQueen: Charlie. He performs nightly at a bar as Barbra Streisand, Cher, and others.
* EmbarrassingFirstName: Aesop Franklin.
* EverybodyKnewAlready: [[spoiler: Sally]] figured out about Cutty's nonexistence weeks before Laurel came out with it. [[spoiler: She went along with it for Laurel's sake ''and'' because the benefits were fantastic.]]
* {{Fainting}}: Camille passes out after Laurel reveals she was Cutty the entire time.
* HystericalWoman: Inverted. Laurel uses this trope to her advantage. During a board meeting, everyone refuses to go over an important business plan because Cutty couldn't make it. Laurel has a phony breakdown and the men agree to read the proposal immediately.
* ImAManICantHelpIt: The press starts making up stories about Cutty having had affairs with multiple women despite supposedly searching for true love. Laurel tells Sally: “He’s a man, that’s how they search.”
* IntrepidReporter / {{Paparazzi}}: Cindy Mason.
* {{Jerkass}}: Frank.
* LatexPerfection: The Cutty mask that Charlie makes for Laurel.
* LineOfSightName: Laurel comes up with the name of her “business partner” after seeing a bartender pour a bottle of Cutty Sark brand Scotch.
* LingerieScene:
** For a film about women’s struggle in the workplace, there are a surprising number of them. Most notably, Camille has a chat with Laurel while trying on [[BlackBraAndPanties lingerie]]. She wears the same getup while trying to seduce Cutty and [[CrowningMomentOfFunny Laurel almost gives herself away when she notices]].
** Frank’s girlfriend slinks around in holiday themed lingerie in one scene.
* MeaningfulBirthDate: Laurel invokes this when creating Cutty, writing his birth date as being around the Crash of 1929.
* MsFanservice: Camille is an in-universe example. She says it herself that men only want to do business with men and they only want [[AllMenArePerverts to sleep with women]]. She follows through with those expectations by throwing herself at men who can help further her career.
* NewYorkCity: The setting for the film. Most of it has to do with Wall Street and other business districts.
* TheNineties: The technology gives it away the most.
* OfficeGolf: Oddly enough, Fallon helps himself to a game of this in Laurel/Cutty's office.
* PluckyOfficeGirl: Sally Dugan.
* ReallyGetsAround: Camille. Laurel-as-Cutty calls her out on this and tells her to use her brain in business rather than…other things.
* TheReveal: Laurel rips off her Cutty mask while accepting the Businessman of the Year Award at the Peabody Club.
* ShipTease: Between Sally and Aesop. Both are fond of telling bad jokes and working with computers. They flirt in the few scenes they share together but it's never explored beyond that.
* ShrinkingViolet: It seems as though Sally falls under this category but once Laurel gives her a chance, she reveals herself to be the PluckyOfficeGirl. And with her computer skills and sweet disposition, Sally proves to be very valuable.
* ShowWithinAShow: Laurel watches Camille on an episode of Sally Jessy Raphael.
* SlapSlapKiss: Laurel and Frank.
* SlowClap: A waiter at the Peabody club starts one after Laurel reveals she was Cutty all along.
* SmokyGentlemensClub: The Peabody Club.
* StealthInsult:
--> '''Camille (dressed in lingerie)''': Discretion is my creed.
--> '''Laurel''': [[DeadpanSnarker Yes, it’s written all over you.]]
* SweetPollyOliver: Laurel disguises herself as a man to gain leverage in business.
* TechnologyMarchesOn:
** Laurel is incredibly impressed when Sally categorizes all her files in the computer. The most glaring example is Sally and Laurel watching the news on Sally’s brand new portable television (complete with a foot long antenna).
** Aseop’s groundbreaking new software looks pretty primitive to modern eyes.
* UnsettlingGenderReveal: When Cutty reveals "his" true identity at the Peabody Club, Camille (who had started rumors about her being pregnant with Cutty's child) passes out cold.
* WhereEverybodyKnowsYourFlame: The bar where Laurel’s DragQueen friend Charlie performs. She goes to him for help making her Cutty costume.
* WhiteCollarWorker: Most characters are upper-level corporate executives, stock brokers, or other business personnel.
* WhiteLikeMe: [[WhoopiGoldberg Laurel]] disguises herself as Cutty, an elderly white man.
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