A young Glaswegian-Italian lounge singer, Toni Cocozza (Ian Hart), has a passion for Frank Sinatra and the dream of becoming a famous musician. He grows weary of playing to elderly crowds in third-rate bars and decides to accept career help from mob enforcer Chisholm (Brian Cox) and his boss Connolly (Iain Cuthbertson) whose wife (Una McLean) has taken a liking to Toni. In exchange for assisting the organization with their illegal activities, Chisholm pays for new clothes for Toni and pressures the producer of a talent show to allow Toni to compete in the contest. Meanwhile, he tries to keep his ties with the mob secret from his friend and accompanist Bill (Alun Armstrong) and pretty cigarette girl Irene (Kelly Macdonald) who he has fallen for. The trio form a modern-day Rat Pack with Irene as Shirley MacLaine. Eventually his luck runs out. While he is helping to rob a store, Toni misses a date with Irene and she and Bill discover that he is leading a double life. They beg him not to compete in the talent show as he will be forever indebted to Chisholm, but he goes anyway. He only places fifth and continues his career singing in lounges, but is deeply unhappy. One day while making a drug drop the drugs he is carrying are stolen by a street kid. Toni refuses to harm the street kid, thus making him a target for the mob hitmen. He performs one last time at a birthday bash for Connolly's wife, fully expecting to be killed after he finishes his number. Bill rescues him by creating a distraction, which gives him a chance to get away with Irene. Using assumed names, the two manage to evade the mobsters and escape to New York City.
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