Song: "Pe$o" (2011)
Album: LIVE. LONG. A$AP
A$AP Rocky's introduction into contemporary hip-hop history began with the unsual boast that'd become an entry point for him to the current rap landscape, and for people who didn't know who Rocky was to become immediate converts and fans: After years of rappers priding themselves on things other than their looks-or, at least, physical features other than flawlessness, like brute strength and/or, for that matter, dick size-Rocky proclaimed himself Harlem's "pretty motherfucker," making his distinctly fine features an atypical hip-hop calling card.