Jay Z's Childhood Friend Tells The Story Behind His New York Magazine Cover

Graffiti legend and photographer Edwin 'PHADE' Sacasa snapped the photo back in 1987.

On Monday New York Magazine revealed the covers to their annual Yesteryear Issue and celebrated NYC's historical music scene with eight front-page images, one of which features a 17-year-old, fresh-faced Jay Z.

The striking photo was taken on January 21, 1987, by Edwin "PHADE" Sacasa, at his birthday party at the Jamaica Colosseum Mall in Queens, New York.

At the time Jay wasn't the star that we know now, but Sacasa was the man, a New York graffiti master and co-founder of early hip-hop fashion icons the Shirt Kings. In the 1980s, the Shirt Kings rose to fame thanks to their customized t-shirts that took famous cartoon characters like Mickey Mouse and the Pink Panther and made them a little more hip-hop friendly, with gold teeth and Fila track suits. Their designs were celebrated not just among hip-hop fans, but rappers as well; including Jay's former mentor Jaz-O.

"It was my birthday party, so a lot of people showed up [DJ] Red Alert, Jaz-O, the Afros, a lot of cats from Hollis, Queens showed up," Sacasa recalled. "Jay just happened to be there with Jaz-O. He was a personal friend of the Shirt Kings."

Sacasa met Jay when he was 14 years old after he was introduced by his Shirt King partner Nike, who lived in the same Marcy Project building as Young Hov. The photo was taken two years before Jigga made his first rap appearance on Jaz's "Hawaiian Sophie" single in 1989, but Sacasa and the Shirt Kings already treated Jay like rap royalty.

"In taking that picture, I knew I was capturing the moment because hanging out with this guy since young I already knew that he had phenomenal skills," Sacasa said. "He was better than anybody that was out... he was already a star in my eyes since he was a kid."

Jay would eventually become a huge rap star, music mogul and fashion icon who helped popularize platinum jewelry, button-up shirts and his own Roc-A-Wear brand. Sacasa says that even back in the '80s, Hov had an impeccable sense of style and he captured all in his now-famous cover image.

"That leather jacket, nobody would even dare wear a [Cincinnati Reds] hat in New York, so he was already creating his own lane and his own fashion statements," he said. "He had a love of clothes and a love of art, which I believe drew him to hang around the Shirt Kings a lot."

There was another picture that Sacasa took that night, one that doesn't appear on the cover of New York Magazine, but lives in Edwin's book "Shirt Kings: Pioneers of Hip Hop Fashion." If you let the Sacasa tell it, the photos from that winter night in 1987 foreshadowed hip-hop's most storied rise to power.

"If you look in my book you'll see a center spread-type shot of the whole birthday party and you'll see Jay-Z is on top. He stood on a chair, he's six feet, but he still stood on a chair and got on top of the whole crowd," Sacasa remembered. "That said a lot to me, that said that this guy, he's destined to be on top some way somehow."