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.

One of the earliest rap beefs was the Bridge Wars between Bronx and Queens rappers over where the birthplace of rap really was. It started with Marley Marl and MC Shan’s “The Bridge,” which claimed that Queensbridge is where rap was officially born, but KRS-One and Boogie Down Productions fought back with the track “South Bronx” and then the “The Bridge Is Over,” which essentially ended the feud and contributed to the end of MC Shan’s career. Blending rap with reggae, “The Bridge Is Over” became an influential song in hip-hop and even included a humorous toss to Billy Joel when he raps in the style of the melody for Joel’s “It’s Still Rock and Roll to Me.”

Royalty issues caused by manager Jerry Heller tore N.W.A. apart, with Ice Cube leaving the group in 1989. Over the course of two albums following his departure, his former crew ripped into the rapper, calling him a Benedict Arnold for leaving. Ice Cube shot back with “No Vaseline” two years after he left, tossing his most searing insults towards Heller and bandmate Eazy-E who he feels sold his soul to their manager. N.W.A. never responded to Ice Cube’s track as a group, though both Eazy-E and Dr. Dre mentioned his disses on solo songs following the dissolution of the group.

By 2001, Jay Z had taken over as the new king of New York’s hip-hop scene. He took advantage of his power with the diss track “Takeover” off the album The Blueprint that was aimed at Nas and Prodigy. He called Nas a has-been, leading to the Illmatic rapper’s vicious response track “Ether,” that goes after Jay Z’s talent, looks and street cred. The style and “fuck Jay Z” background repetition was mimicked by Remy Ma on her Nicki Minaj diss track “Shether.”

“I ain’t got no motherfuckin’ friends,” Tupac says right at the beginning of the vicious, anti-East Coast “Hit ‘Em Up” that he released with his group Outlawz. “That’s why I fucked your bitch, you fat motherfucker.” From there, the rapper launched into an all-out tirade and threat aimed at his former friend Notorious B.I.G. and the rest of the Bad Boy crew, threatening to kill Biggie, Puff Daddy, Lil Cease and Mobb Deep. To add insult to injury, the official music video featured actors playing Biggie and Lil Kim, who he also insults on the track.