Recent research suggests that emotional music clips can serve as a highly successful tool for eliciting rich autobiographical memories, and that the utility of these cues may be related to their subjective familiarity. The current study was designed to examine the effects of familiarity on phenomenological characteristics and neural recruitment during retrieval of autobiographical memories elicited by musical cues. Further, we were interested in understanding how these effects differ as a function of age. In an event-related functional neuroimaging study, participants retrieved autobiographical memories associated with age-specific popular musical clips. Participants rated song familiarity, as well as the temporal specificity and emotional valence of each memory. Song familiarity was associated with increased dorsal medial prefrontal cortex (dmPFC) activity and ratings of temporal specificity and positivity across participants. In addition, behavioral and neuroimaging findings suggest age differences in familiarity-related effects in which familiarity was more associated with enhancement of memory detail in young adults and affective positivity in older adults. These findings highlight important age-related shifts in how individuals retrieve autobiographical events and how personally relevant musical cues may be used to facilitate memory retrieval.