This paper examines a literacy program, Dialogic Literary Gatherings, that improves the literacy levels of urban students and their families while tearing down elitist walls and cultural stereotypes. In the Dialogic Literary Gatherings, participants read and discuss books from the canon of classical literature, such as James Joyce’s Ulysses, texts traditionally reserved for the elite. Three case studies were carried out in urban schools in Spain within the frame of the European project INCLUD-ED (6th Framework Programme). In the schools analysed, the Dialogic Literary Gatherings take place with students and also include a family education program with family members, mostly from cultural minorities with non-academic backgrounds. Data collection at each school involved standardized open-ended interviews with four students, three teachers, three family members, and one focus group of teachers. Findings indicate that the Dialogic Literary Gatherings with family members raise the literacy levels of parents, increase the learning interactions between parents and their children, and strengthen families’ relationships with schools. This paper also shows that families from low socio-economic backgrounds, low levels of education, and even those considered illiterate from any cultural background (including children) can become highly motivated for highly sophisticated literary practices, including the reading of classical literature.