In the pantheon of early rap, few tracks had the reach of UTFO’s “Roxanne, Roxanne.” It wasn’t just the Billy Squier sample (a break later used by dozens of artists, including on JAY-Z’s “99 Problems”), or the playful, tongue-twisting style Kangol Kid called “z-rap” (the “fo’ shizzle” you hear in Too $hort, E-40, Snoop, and others). It was the sheer number of response records the song generated—a phenomenon that both presaged viral culture and established rap as the most dynamic, dialogic culture in pop. The tracks here don’t just capture the best of UTFO, they’re a snapshot of rap at the transformative moment when it was pushing the music toward the mainstream—a shift as seismic as the development of rock ’n’ roll.