The film also features Jon Lovitz and Rosanna Arquette and Lisa Rinna and Barry Newman as a married couples in supporting roles.

Ryan Turner (Sheen) is an arrogant broker living a Playboy lifestyle in New York City with his conceited girlfriend Cindy Styne.

Ryan, convinced that this could be his big break, informs all his clients of the huge deal that is going to happen and they all place large amounts of money into the merger.

Depressed, he lounges around all day, until Cindy tells him that she is leaving for Brazil with another man, dumping Ryan who she now considers "a loser" for a diamond mine owner.

Inevitably, she ruins the whole transaction, as she is incapable of expressing the sympathetic advice that Ryan was offering in her absence, and Simpson's stock plummets.