Laurel Ayres, Whoopi Goldberg, is a sharp-minded investment banker climbing the Wall Street ladder, until a promotion denial reveals the gender bias that holds her back. Her less intelligent male protege, Frank Peterson, Tim Daly, is promoted instead, pushing Ayres to quit and strike out on her own. When she tries to launch a new company, she discovers that the male-dominated world of finance refuses to take a Black woman seriously, so she fabricates a fictional white man, Robert S. Cutty (an inspiration drawn from the Cutty Sark bottle), to act as the public face of her talents.
Ayres conducts extensive research into the cultural codes and performative signals that influence how men perceive power, aiming to navigate the tricky terrain of Wall Street with a convincing persona. She is aided by Sally Dugan, Dianne Wiest, a computer-savvy secretary whose own talents have long gone underappreciated. Together, they build a formidable, independent stockbroking operation and even help a struggling high-tech computer company survive.
But the ruse creates tension as Cutty begins to gather credit for ideas that are really Ayres’ and Dugan’s. Rival firms and intrusive tabloid reporters hustle to bring Cutty into the spotlight. To keep the masquerade alive, Ayres recruits her best friend from the club scene, Camille Scott, Bebe Neuwirth, a performer who works as a female impersonator, to craft a more convincing disguise and facial prosthetics that will let Ayres slip into Cutty’s role.
When that plan falters, Ayres and Dugan decide to escalate, but the scheme spirals out of control and they are charged with Cutty’s murder. Frank, quietly aware of the truth, uncovers the deception and uses it to his advantage, pressuring the duo so that he can become Cutty’s front man. The conflict tests loyalties and ambition, forcing each player to reckon with a system built on race and gender hierarchies.
In the climactic sequence, Ayres suits up in the Cutty disguise one final time to attend a private club meeting where Cutty’s awards are handed out, choosing to reveal her true identity in front of the male-dominated audience. The act becomes a deliberate, public challenge to the power structures that sidelined her. With new recognition, Ayres launches a substantial business empire, putting friends and trusted allies in leadership roles and reshaping the landscape for women and people of color in finance. Frank, meanwhile, faces the consequences of his own maneuvering and finds himself sidelined in the corporate world he hoped to enter.
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