Bernie has a seven year deal with his old-style thug boss Shelley, played by the aptly cast Alec Baldwin. In order to work off a gambling debt caused by his addiction combined with a losing streak, Bernie "cools" the luck of winners at the Shangri-La casino simply by circulating around to wherever there has been too much of a winning streak going on. It works, and he keeps the outdated Shangri La nicely profitable. But now his obligation to Shelley is nearly finished and Bernie wants out of the business. No smart old stickler like Shelley is going to let such a good thing go so easily, however, and he contrives a cruel and clever plan to trap Bernie into extending his contract using the only bait that could tempt a guy with nothing else to lose: a sexy new love interest in the form of cocktail waitress Natalie (Maria Bello).

Once in a while a role comes along for which there is really only one actor that can jump start it to life properly, and without a doubt William H. Macy is that actor for Bernie Lootz. With his kicked-puppy looks and his quietly resigned demeanor, Macy is superb in this movie. In fact, he really made the movie, period.