Good Advice (2001)

Synopsis
In this comedy, Ryan Turner (Charlie Sheen) is a successful young stockbroker whose life falls apart seemingly overnight when Donald Simpson (Barry Newman), the owner of a powerful media conglomerate, gives him some particularly bad advice about a certain stock; this might have something to do with the fact Ryan has been having an affair with Veronica (Lisa Rinna), Simpson's wife. Ryan loses his job, he finds himself banned from stock trading, and he's about to be evicted from his apartment when his live-in girlfriend Cindy (Denise Richards) decides to leave him to fly off to Rio with a new man. As Ryan tries to come up with a way to pay his rent, he gets a call from Cindy's boss; she writes a newspaper advice column, and it seems her copy is long overdue. Needing Cindy's paycheck to keep a roof over his head, Ryan begins writing her column for her, leading to a wealth of complications and misunderstandings. Good Advice also stars Jon Lovitz, Rosanna Arquette, and Estelle Harris. ~ Mark Deming, All Movie Guide