Unlucky Bernie Lootz (William H. Macy) works at the Shangri-La casino as a "cooler" - a man with professionally bad luck designed to stop people from winning. A cocktail waitress, Natalie (Maria Bello), takes no notice of Bernie, who is smitten with her. The casino manager, Shelly (Alec Baldwin) prides himself on running a "classically" Vegas casino and resents the new places that attract a lower clientele. The owners, however, hire an advisor named Larry (Ron Livingston) to help bring in more money with techniques contrary to Shelly's outdated policies. Bernie informs Shelly that he's leaving town in a week. After an encounter during which Bernie rescues Natalie from an aggressive customer, she appears to take an interest in him. They begin dating, but Bernie is apprehensive due to his bad luck. He reveals that he used to be a gambling addict in huge debt to several casinos. Shelly "saved" him by breaking his kneecap and paying off his debt in exchange for Bernie's work as a cooler for 6 years, which ends at the end of the week. Bernie and Natalie run into his estranged son Mikey and his pregnant wife Charlotte who are scamming a diner by faking labor. Bernie tells Mikey to stop by sometime.