Sick of living with his in-laws, Italian American Buddy Visalo wants to buy a house and finds one in Staten Island. It's a run-down two family house, built in 1912 in a "mick" (Irish) neighborhood. The real estate agent tells him the upstairs is a completely separate apartment that rents for $80 a month. Buddy's friend Chip tells him he wouldn't have to work, but Buddy gets the idea that he and his wife Estelle could live in the upstairs and turn the downstairs into a bar where Buddy himself would provide the live entertainment. A flashback scene shows how Buddy was singing in the army during WWII and seen by the famous radio host and entertainer, Arthur Godfrey. Godfrey tells Buddy to see him when the war's over, but when it is, Estelle tells Buddy he can't see Godfrey if he wants to marry her. Estelle has all kinds of ideas about being respectable and thinks Buddy will make a fool of himself. Feeling like he's missed his big chance, Buddy has since been trying for success by getting into business for himself in one scheme after another with disastrous results.
Buddy goes ahead with the house purchase and Estelle hates it on sight. Then Buddy finds out the upstairs renters, Jim and Mary O'Neary, aren't paying rent. When Buddy and his friends decide to throw the O'Neary's out, Mary O'Neary goes into labor and has her baby, which turns out to be colored! Mr. O'Neary deserts Mary and then Estelle demands that Mary move out too. With a colored baby, there is really no place for Mary to go. Troubled by Mary's plight, Buddy does an unselfish thing--he gets an apartment for her until she can get back on her feet and checks in on her from time to time. Their friendship develops and deepens into an affair.
Meanwhile, Estelle gets a letter from the bank stating that their expenses are two and a half times their income and decides not to tell Buddy. She plans to keep spending until their savings run out and Buddy HAS to sell the house. Unfortunately, Buddy finds out and starts working a 2nd shift, after which he goes and visits Mary. Estelle finds out the truth about Buddy's actual work hours, follows him and discovers the affair. She moves back with her parents immediately, trashing all the remodeling work done on the bar before she leaves. Buddy decides to break it off with Mary, who has decided to give up her baby, and Buddy and Estelle arrange a meeting to clear the air. Will Buddy be able to win Estelle back and finally realize his dream to be a singer and a "success"? Where will Mary, and Mary's baby finally end up? One thing is for sure, no matter whose dreams are realized, someone else's dream has to shatter. This film won the Audience Award at the Sundance Festival in 2000 and deservedly so.