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Laurel Ayers is a businesswoman trying to pave a way for herself on Wall Street, a society dominated by 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, Laurel disguises herself in prosthetics 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 nosy gossip columnist and a stock broker who has a reputation for 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.
- All Men Are Perverts: The fact that an important lunch meeting is held at a strip club makes it pretty obvious.
- Ambition Is Evil: Averted. If it weren’t for Laurel’s ambition to implement her own ideas, Syntonex would have gone bankrupt.
- Aren't You Going to Ravish Me?: Camille’s reaction to Cutty’s disinterest in her.
- Black Bra and Panties: Camille wears it well.
- Buxom Is Better: 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.
- The Cameo: Golf player Johnny Miller and Donald Trump.
- Cigar Chomper: 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.
- Corrupt Corporate Executive / There Are No Good Executives: Played straight. Even 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.
- Double Standard: 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.
- Drag Queen: Charlie. He performs nightly at a bar as Barbra Streisand, Cher, and others.
- Embarrassing First Name: Aesop Franklin.
- Fainting: Camille passes out after Laurel reveals she was Cutty the entire time.
- Hey, It's That Guy!:
- Hysterical Woman: 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.
- I'm a Man, I Can't Help It: 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.”
- Intrepid Reporter / Paparazzi: Cindy Mason.
- Jerkass: Frank.
- Latex Perfection: The Cutty mask that Charlie makes for Laurel.
- Line-of-Sight Name: Laurel comes up with the name of her “business partner” after seeing a bartender pour a bottle of Cutty Sark brand Scotch.
- Lingerie Scene:
- 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 lingerie. She wears the same getup while trying to seduce Cutty and Laurel almost gives herself away when she notices.
- Frank’s girlfriend slinks around in holiday themed lingerie in one scene.
- Ms. Fanservice: Camille is an in-universe example. She says it herself that men only want to do business with men and they only want to sleep with women. She follows through with those expectations by throwing herself at men who can help further her career.
- New York City: The setting for the film. Most of it has to do with Wall Street and other business districts.
- The Nineties: The technology gives it away the most.
- The Not-Secret: Sally figured out about Cutty's nonexistence weeks before Laurel came out with it. She went along with it for Laurel's sake and because the benefits were fantastic.
- Office Golf: Oddly enough, Fallon helps himself to a game of this in Laurel/Cutty's office.
- Plucky Office Girl: Sally Dugan.
- Really Gets Around: Camille. Laurel-as-Cutty calls her out on this and tells her to use her brain in business rather than…other things.
- The Reveal: Laurel rips off her Cutty mask while accepting the Businessman of the Year Award at the Peabody Club.
- Ship Tease: 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.
- Shrinking Violet: It seems as though Sally falls under this category but once Laurel gives her a chance, she reveals herself to be the Plucky Office Girl. And with her computer skills and sweet disposition, Sally proves to be very valuable.
- Show Within a Show: Laurel watches Camille on an episode of Sally Jessy Raphael.
- Slap Slap Kiss: Laurel and Frank.
- Slow Clap: A waiter at the Peabody club starts one after Laurel reveals she was Cutty all along.
- Smoky Gentlemen's Club: The Peabody Club.
- Stealth Insult:
Camille (dressed in lingerie): Discretion is my creed.
Laurel: Yes, it’s written all over you.
- Sweet Polly Oliver: Laurel disguises herself as a man to gain leverage in business.
- Technology Marches On:
- 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.
- Where Everybody Knows Your Flame: The bar where Laurel’s Drag Queen friend Charlie performs. She goes to him for help making her Cutty costume.
- White Collar Worker: Most characters are upper-level corporate executives, stock brokers, or other business personnel.
- White Like Me: Laurel disguises herself as Cutty, an elderly white man.