The goal of this study was to examine whether popularity and likeability were related to associating with popular peers in adolescence. Participants were 3,312 adolescents (M age = 13.60 years) from 172 classrooms in 32 schools. Four types of peer affiliations of the participants with the popular peers in their classrooms were distinguished: “best friends,” “respected,” “wannabes,” and “unrelated.” Two types of benefits of affiliating with high-status peers were identified: achieving high status or popularity for oneself, and becoming liked by others. The results showed that popularity was associated with being closely affiliated with popular peers, whereas likeability was more strongly predicted by a more distant relation with popular peers. Results suggest that close affiliation with popular peers increases popularity, but come at the expense of reduced likeability in the peer group at large.