5. "Roxanne's Revenge," Roxanne Shante
Of all the hip-hop rivalries in the genre's history, the early Roxanne Wars yielded the highest number of tracks with reportedly 100 songs recorded by various MCs during the time. It all began with U.T.F.O.'s "Roxanne, Roxanne," a major hit about being rejected by a girl named Roxanne. What caused the innocuous hit to spiral out, was the timing of 14-year-old Lolita Shanté Gooden offering to help a local DJ get back at U.T.F.O. for canceling a promotional radio appearance. She took on the name Roxanne Shanté and released the hit "Roxanne's Revenge," told from the perspective of the girl who rejected the group. U.T.F.O. responded by enlisting a woman named Elease Jack to record a response track titled "The Real Roxanne" under the same name. From there, many other MCs and artists contributed the ongoing "feud" with songs aimed at Roxanne and members of Roxanne's family.