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Jay-Z and The Notorious B.I.G.’s times in the music industry might have only overlapped for less than a year, but the two rappers shared a strong connection. They hailed from the same neighborhood of Bedford-Stuyvesant in Brooklyn, and even attended the same high school. When they had started rapping seriously, they often pushed each other to be better.

Jay-Z, who was once friends with Biggie Smalls, pictured wearing blue in 1996
Jay-Z in 1996 | Al Pereira/Getty Images/Michael Ochs Archives

Jay-Z and The Notorious B.I.G. became good friends and recorded ‘Brooklyn’s Finest’ together

Jay-Z and The Notorious B.I.G. both were in the same line of work before they started rapping: they were crack dealers on the streets of Brooklyn at the height of the crack epidemic. Biggie gained a reputation around the neighborhood not just for standing on the corner, but for his rapping abilities whenever he’d get on a mic at local cyphers or parties. Biggie eventually linked up with record executive Sean “Diddy” Combs and released his debut album Ready to Die in September 1994.

Biggie’s longtime friend and Junior M.A.F.I.A. groupmate Lil’ Cease reflected on Biggie’s relationship with Jay-Z in a 2016 Instagram Live with Smoke DZA.

“Big met [Jay-Z] at the Palladium and they bonded just on some G s*** because they respected each other as men and they respected each other as artists,” he said. “Big wasn’t afraid to tell that; Big thought he was doper than him. Big used to say, ‘Yo, that n**** nicer than me.'”

Jay-Z released his own debut album Reasonable Doubt in 1996. The album featured the Notorious B.I.G. collab “Brooklyn’s Finest,” as well as the hit single “Dead Presidents II” — a song that signaled to Biggie that he had been beaten at his own game. “When Jay-Z said that line on ‘Dead Presidents,’ ‘N**** take a freeze off my kneecap / N**** believe that,’ Big was like, ‘Yo, he got me,'” Cease said.

The Notorious B.I.G.’s ‘Life After Death’ demos ‘worried’ Jay-Z

Biggie continued to work hard on his own album, titled Ready to Die and slated for release in March 1997. Justin Tinsley’s 2022 book It Was All a Dream: Biggie and the World That Made Him detailed the recording process for the album, including what Jay-Z thought when he first heard the album before its release.

“I remember when he was doing Life After Death and he sent me four songs in the demo stage,” Jay said. “I was like, ‘Oh my God! We got a problem!’ I was happy for him and I was upset for myself. I was a little worried about myself as an artist.”

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The Notorious B.I.G. died as Jay-Z was gaining popularity

The Notorious B.I.G. died on March 9, 1997 in Los Angeles, just two weeks before Life After Death hit store shelves. The music industry was shocked by Biggie’s sudden death, especially given the death of his onetime friend Tupac Shakur in a similar fashion just six months before.

Biggie was on the phone with Jay-Z just an hour before his death, gushing about the grand plans he had for both of them as they continued their rise from Bed-Stuy to the top.

Jay-Z went on to release his sophomore album In My Lifetime, Vol. 1 in November 1997.