By the time of Sidewalk University’s release, Shinehead had established himself as a key player on New York’s flourishing dancehall scene. He'd made a name for himself as one of the sharpest deejays working for Tony Screw’s legendary Downbeat International soundsystem and displayed a truly startling stylistic versatility on record, coming across as a ruthless microphone controller at one moment and a silken-voiced crooner the next. Shinehead’s eclecticism attracted the attention of Elektra Records, which recognized his ability to appeal to listener sensibilities ranging from dancehall and reggae to hip-hop and R&B. Sidewalk University was Shinehead’s third full-length for Elektra and saw him finally achieving the crossover hit the label had long hoped for. This came in the form of “Jamaican in New York,” a lighthearted remake of Sting’s 1988 hit “Englishman in New York”; it was tender enough to appeal to mainstream listeners but kept a real emotional heft that made it an anthem for expatriate Jamaicans not just in New York, but the world over.