Dapper bank robber Billy (Patrick Dempsey) plans one final heist in order to buy a sailboat and sail away with his cheating girlfriend Selina. A misstep involving the security cameras leads to Billy's face being broadcast all over the news, and he retreats to the seedy "Heartbreak Hotel" to wait for the heat to die down. It doesn't take long for his fellow patrons to begin extorting him for their silence. The mounting pressure and discovery of Selina being unfaithful push Billy into the arms of a prostitute named Priscilla, who soon falls for him.