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Investment banker Laurel Ayres is a smart and single woman trying to make it up the Wall Street corporate ladder, until one day she finds out that she is passed over for a promotion because she is a woman. Unable to face the fact that her less smart and sexist male protege (Frank) has now become her boss, she quits and tries to start up her own company only to find out that the male dominated world of Wall Street is not interested in taking an African American woman seriously, and thus is forced to create a fictional white man (Robert S. Cutty) in order to be judged on her own merits. Ayres financial wisdom is joined by the intelligent and computer-savvy secretary Sally Dugan who also was not properly recognized for her talents, and together they are able to become the most successful independent stock brokers in the world while helping a struggling high tech computer company stay afloat.
However, the ruse eventually runs into problems, as Cutty is still getting credit for Ayres great ideas, and competing firms and tabloid journalists are willing to do anything in order to bring the wealthy and elusive Cutty into the public and on their side. Thus Ayres is forced to get her best friend (who works at a nightclub as a female impersonator) to create an effective disguise in the mould of Marlon Brando to try to fool the naysayers; when that fails, she and Dugan decide to kill Cutty only to be charged with his murder. Frank uncovers the ruse and pretends that he is now the front man to world famous Cutty.
The film ends with Ayers donning the Cutty disguise one last time to attend a meeting of the exclusive gentlemen's club to accept Cutty's awards and unmasking herself in order to teach the male dominated industry the evils of racial and sexual discrimination. Ayers is finally given credit for her work and creates a huge business empire with her friends at the helm. Frank attempts to land a job with the business, only to be laughed off.
- Whoopi Goldberg as Laurel Ayres / Mr. Cutty
- Dianne Wiest as Sally Dugan
- Eli Wallach as Donald Fallon
- Tim Daly as Frank Peterson
- Bebe Neuwirth as Camille Scott
- Austin Pendleton as Aesop Franklin
- Lainie Kazan as Cindy Mason
- George N. Martin as Walter Manchester
- Marie Holst as Dancer
- Kenny Kerr as Charlie
- Donald Trump (as himself) gives Laurel's former boss (Frank) some come-up-ance by pulling his assets from Frank's firm to invest them at Laurel's.
- Laurel convinces another billionaire to invest with her by giving him the opportunity to play a round of golf with his hero, Johnny Miller (as himself).
Peter Stack of the San Francisco Chronicle finds Goldberg "very funny playing out her scheme, which inevitably backfires" and opines that "it's the peripheral characters that give the film its comic momentum."
Contrastingly, Roger Ebert writing in the Chicago Sun-Times, gave this film two stars, calling it "an uninspired recycling of the Tootsie formula. Though the film "scores some good points against the male-dominated hierarchy of the business world," Ebert is ultimately unconvinced by the Cutty character.
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