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The Notorious B.I.G. is a hip-hop legend and an icon of New York rap. The Brooklyn-bred emcee had a braggadocious personality and equally braggadocious lyrics. When he was in high school on his way to stardom, he crossed paths with several other future high-profile figures.

The Notorious B.I.G. performing in 1995
The Notorious B.I.G. | Chris Walter/WireImage

The Notorious B.I.G. grew up in Brooklyn

The Notorious B.I.G. grew up in the Brooklyn neighborhood of Bedford-Stuyvesant. He came of age during the crack epidemic, and even started selling crack himself at age 12 to make money.

When he was a teenager, Biggie often participated in rap battles on the street and quickly made a name for himself as the hottest new rapper on the block. He was also a noted straight-A student in school and grew up Catholic.

Biggie attended Bishop Loughlin Memorial High School in Brooklyn before eventually transferring to George Westinghouse Career and Technical Education Center.

The Notorious B.I.G. performing
The Notorious B.I.G. | David Corio/Redferns

The Notorious B.I.G. went to the same high school as Rudy Giuliani

Bishop Loughlin Memorial High School is a private Catholic school not far from where Biggie grew up. He eventually chose to leave the school to go to Westinghouse High School and focus his attention on his creative pursuits.

Biggie isn’t the only famous alumnus to come out of Bishop Loughlin High School: former New York City mayor Rudy Giuliani and actors such as Vincent Schiavelli and Doug E. Dougs have all attended the private school.

After graduating from Bishop Loughlin High School, Giuliani went on to study at Manhattan College in the Bronx, and later went to law school at New York University. He launched his career as a lawyer in the 1970s, and became one of the Reagan administration’s top cops in the 1980s.

Former New York City Mayor Rudy Giuliani makes an appearance in support of fellow Republican Curtis Sliwa who is running for NYC mayor on June 21, 2021 in New York City. The Guardian Angels founder has said he will rollback bail reforms, support police and keep Rikers Island open rather than following the current plans to close it. Sliwa is running against Fernando Mateo, president of the New York State Federation of Taxi Drivers with the winner facing off against the winner of the Democratic primary.
Former Mayor of New York City Rudy Giuliani | Spencer Platt/Getty Images
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The Notorious B.I.G. later went to high school with Jay-Z and Busta Rhymes

After Biggie moved on from Bishop Loughlin to George Westinghouse High School, he crossed paths with other classmates who would go on to become iconic rappers themselves: Jay-Z, DMX, and Busta Rhymes.

At one point, Jay-Z and Busta Rhymes even got into a rap battle themselves. Jay-Z recounted the story in a 2015 interview on Jimmy Kimmel Live!. “Me and Busta Rhymes actually had a rap battle in the lunchroom,” he remembered. When asked who won the battle, he simply shrugged, proudly implying that he did.

Busta Rhymes reflected on the battle in a 2020 interview on the 85 South Show podcast.

“Ultimately, Hov got the best of the battle in that moment,” Busta admitted. “I was just starting to figure out how to master my fascination with the speed rap. He was already on it. He was doin’ it at an incredible level of skillset. And was displayin’ that s— like — water spillin’ all over the place. Just takin’ shape and form whatever way he felt like it ‘cause he had been on his s— with it.”

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