Shelly Kaplow (ALEC BALDWIN) is an old school casino operator in Las Vegas who doesn't like what Sin City has turned into. Nor does he like the fact that owner Nicky "Fingers" Bonnatto (ARTHUR J. NASCARELLA) has brought in Larry Sokolov (RON LIVINGSTON), a young maverick who wants to make various changes. He wants to start by jettisoning veteran performer Buddy Stafford (PAUL SORVINO) in favor of the more modern act provided by Johnny Capella (JOEY FATONE).
Shelly still has an ace up his sleeve, however, in the form of Bernie Lootz (WILLIAM H. MACY), one of the unluckiest guys on the Strip. In fact, Bernie's bad luck is so contagious that Shelly uses him on the casino floor as a "cooler" who steals gamblers' luck when they suddenly get hot.
Having paid off his debt to Shelly for gambling debts incurred long ago. Bernie wants to retire, especially after meeting and immediately falling for Natalie Belisario (MARIA BELLO), a new cocktail waitress at the casino who seems to like him as well.
Bernie's good fortunes, however, are short-lived. His deadbeat son, Mikey (SHAWN HATOSY), and his pregnant girlfriend Charlene (ESTELLA WARREN) suddenly show up, wanting money and looking to make some quick bucks - legally or not - at the casino. That obviously doesn't sit well with Shelly, but more troubling to him is that Bernie's new good mood has apparently siphoned his "cooling" abilities.
As he hopes to get out of the business and live a life without bad luck, Bernie must deal with various forces and developments that apparently don't want any of that to happen.