Since the end of the 1970s, Bologna has represented an ‘urban mythscape’ for left-wing subcultural youth in the Italian cultural imaginary. This article examines representations of spaces of encounter and conflict for young people in Bologna in Silvia Ballestra’s La guerra degli Antò (1992) and Enrico Brizzi’s Jack Frusciante è uscito dal gruppo (1994). Set in the 1990s, these novels mark a significant change in Bologna’s urban mythscape, in that they do not refer back to the 1970s like the majority of cultural representations of youth set in Bologna. The protagonists’ desire to ‘leave society’ and withdraw into private spaces reflects an evolution in representations of Italian subcultural youth, which mirrors the emergence of Italian ‘Generation X’ and their experience of social and political commitment.