Film Synopsis

Set during the 1950s in Staten Island, the film charts the financial failures of Buddy (Michael Rispoli), a nice-guy entrepreneur who has perpetual bad luck. While he was in the army, he sang songs on stage to bolster troop morale. During one performance, he received a warm reception from none other than Arthur Godfrey, who invited him to audition when he got back to the U.S. After the war, Buddy's crushingly pragmatic wife Estelle (Katherine Narducci), along with her very traditional parents, dissuade him from a life in showbiz. After a decade of living with Estelle's parents and failing repeatedly at one get-rich-quick scheme after another, Buddy buys a rundown house with the idea of refurbishing the second floor for living quarters and the first for a pizzeria where he can sing. Estelle grudgingly goes along with it, secretly hoping that this plan will fail so disastrously that he will stop dreaming and lead a "normal" life. Not until he finalizes the purchase does Buddy realize that the house has a pair of squatters: Jim (Kevin Conway), a drunken Irish immigrant, and his much younger, very pregnant girlfriend Mary (Kelly Macdonald). Buddy tries to evict the recalcitrant drunkard, but he refuses to leave. Just as matters are about to come to fisticuffs, Mary goes into labor. To the surprise of everyone, the child is of mixed race — the product of a brief tryst that Mary had with an African-American man a while back. Disgusted and disappointed, Jim shuffles off, never to be seen again. Buddy hasn't quite the heart to evict a young single mother, nor the strength to resist his wife's perpetual nagging, so he quietly pays for a room in a neighborhood boarding house. Though Mary is initially very mistrustful of Buddy's intentions, the two slowly realize that they are in fact soulmates.