A former Prohibition-era Jewish gangster returns to the Lower East Side of Manhattan over thirty years later, where he once again must confront the ghosts and regrets of his old life.

Ruby Dennis is an middle-aged man with an unfulfilled ambition as a singer. As he begins to pursue that ambition, his family falls apart.

Offbeat fashion student Betsy Hopper and her straight-laced investment-banker fiancé Jake Lovell just want an intimate little wedding reception, but Betsy's father Eddie, a Long Island construction contractor, feels so threatened by Jake's rich WASP parents that he blows the ceremony up into a bank-breaking showpiece, sending his wife Lola into a financial panic.