Wall Street wonder boy Ryan Turner (Charlie Sheen) has it all. He just can't lose- until he gets a bum stock tip. Ryan secretly writes his (now) ex-girlfriend Cindy's (Denise Richards) column. On the verge of getting fired, Page (Angie Harmon), Turner turns to his plastic surgeon Barry (Jon Lovitz) for help. Once a boorish, insensitive guy, he transforms the column, and himself, in to a winner.