It stars Whoopi Goldberg, Dianne Wiest, Eli Wallach, Tim Daly, and Bebe Neuwirth, alongside Austin Pendleton and Lainie Kazan.

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 being passed over for a promotion because of her gender.

Unable to face the fact that her less intelligent male protege, Frank Peterson, 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 (inspired by a bottle of Cutty Sark) to legitimize her talents and make her professionally relevant in said world.

Ayres is forced to recruit her best friend (who works at a nightclub as a female impersonator) to craft a disguise, complete with facial prosthetics, so she can appear as "Cutty" and fool the naysayers.

[4] 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".