The purpose of this chapter is to consider how the interpretive lens of the (post)subcultural researcher squares with the hefty legacy of the subculture–post-subculture debate—if we are any closer to uncovering more fine-grained insights into the lifeworlds of ‘youth culturalists’ or if we are still in the business of creating these lifeworlds on behalf of youths? The chapter is based on a series of reflections on my own career as a youth culture researcher and an ongoing series of conversations with my son in which the then and now of youth cultures is invariably a topic of discussion. I claim no universal truths in this account. It is instead an opportunity to reassess what myself and other youth researchers have suggested about the nature of youths and their cultures and to ponder all of this in the context of an era where youth culture is as much a historical terminology as something that bespeaks a contemporary status quo for young people.