Strictly Business (1991)

A hilarious film about a successful "buppie" investment broker (Joseph C. Phillips) who risks his career, fiancé and possessions when he becomes infatuated with a beautiful club promoter (Halle Berry) who finds him staid and boring.

With the aid of a mailroom clerk (Tommy Davidson) at his firm, he gets a crash course in the wilder side of life to help him meet the woman

Co-starring Samuel L. Jackson, Anne-Marie Johnson, Kim Coles and Ellen Cleghorne.