Lots of famous rappers hone their skills during high school rap battles, but very few face the stiff competition of Jay Z, who attended Brooklyn’s George Westinghouse Career and Technical Education High School with Busta Rhymes and Notorious B.I.G. “Me and Busta Rhymes actually had a rap battle in the lunch room,” the hip-hop mogul says in a clip from his Thursday appearance on Jimmy Kimmel Live!. Pushed by the host to share who “won” the showdown, Jay Z smirks and hints to himself: “I love Busta Rhymes, but…”
Over the years, Jay and Busta Rhymes have often reminisced about their teenage rapping rivalry during interviews. “I didn’t know Biggie rhymed in school ’cause in school we was cuttin’ a lot of class and we was smokin’ a lot of weed and bullshittin’,” Busta told Fuse in May. “I knew Jay Z was rhyming ’cause me and Jay Z battled in school, speed rapping. He had finessed the speed rapping phenomenally at that time and I was new with the speed rapping, but losing that battle to Jay in speed rapping is what made me one of the most dangerous speed rappers today … Jay know he can’t see me in no speed rapping today.”
Elsewhere in the Kimmel interview, Jay Z reflects on his first stage performance, during which he “forgot the lyrics.” The host also surprises the rapper with a clip from his first television performance –alongside Big Daddy Kane – where a youthful Jay shows off with an impressive freestyle filled with nimble triplets. Visibly embarrassed by the footage, the rapper makes fun of his younger self’s collared shirt and haircut.