Charlie Sheen plays Ryan Turner, a hotshot broker living an upscale life in New York City with his shallow girlfriend Cindy Styne (Denise Richards). One morning, he is playing golf with the owner of one of the biggest newspaper publishers of New York. He tells Ryan of a huge merger between his company, Simpson Inc. , and a large drug corporation. Ryan, ecstatic that this could be his big break, calls all his clients and informs them of the huge deal that is going to happen and they all place large amounts of money into the merger. However, the next day, Simpson reveals that there is not going to be a merger. Ryan loses most of his own, and much of his clients' money in light of the news. He storms over to Simpson's office, and Simpson tells Ryan that he personally screwed him over because Ryan was sleeping with his wife. Ryan, now near bankrupt, sells his possessions and moves in with his girlfriend, Cindy. Ryan tries to get another job at another brokerage, but his license is revoked. Devastated, he loafs around, until Cindy tells him that she is leaving for Brazil with another man.