Unearthed Photos of Hip-Hop Royalty from the 80s and 90s

On a sunny September day in Harlem 20 years ago—just over a year after Biggie’s death and two years after Tupac’s—XXL magazine made music history with a photograph. Staff reached out to hundreds of hip-hop pioneers to recreate A Great Day In Harlem, the iconic image of jazz legends like Dizzy Gillespie, Thelonious Monk, and Gene Krupa hanging out on a Harlem stoop, shot on August 12, 1958 by photographer Art Kane for Esquire magazine. For the hip-hop version, XXL commissioned legendary black photographer Gordon Parks.

The editorial team had no idea how many rappers would show, but the turnout overwhelmed their expectations. More than 100 hip-hop artists—from the East to the West Coast, old school to new—piled onto the cement steps of 17 East 126th Street, where the original photo was shot decades before. Among them were Rakim, Busta Rhymes, members of The Roots and A Tribe Called Quest, Pete Rock, Grandmaster Flash, Slick Rick and many others.

In a video shot by Nelson George documenting the day, Mos Def seems stunned by the sheer number of legends in attendance, pointing out how surreal it is seeing everyone together midday. The photo almost didn’t happen, because Parks’s team struggled to pry rappers out of embraces to position them. They spilled over onto a third stoop, and as time passed, a dark shadow crept across the street, threatening to ruin the shot. Just as a voice yelled, “We’re losing Jermaine Dupri,” Reverend Run popped up last minute, slowly strolling up the block and falling into formation like the last puzzle piece before Parks captured the moment.

People who were there reminisced about the day at an event in November at the Schomburg Center in Harlem. Writer Miles Lewis referred to the image as “hip-hop’s graduation photo,” and Fab Five Freddy called it the last moment of “the golden era” before the genre took on new life in other regions of the world.

Yet for all the photo’s significance, it simply hadn’t become nearly as famous as the original or a number of other hip hop photos that came to represent the era. I saw it for the first time spread across the opening pages of Contact High, a new photography book chronicling hip hop’s rise, told by photographers revisiting their contact sheets of iconic and little-known shoots. “It was like asking someone to see their diary,” author Vikki Tobak told VICE. “[These contact sheets] were never meant for public consumption. It shows all of their mistakes, and it shows the artists’ mistakes too where they’re being awkward or overly trying to be a certain way. But that’s important right now when images are really perfect, to say it’s all a process.”

More than that, by shifting attention to images that are forgotten and unpublished, Contact High shows how much more there is to learn about an era casual fans think they know from the few images that still circulate online. Some of the photographers featured in the book even rediscovered shoots they hadn’t thought about in decades, finding renewed significance in the snapshots they’d captured.

Many of the photos in the book are ones author Vikki Tobak remembered from her years covering hip-hop as a journalist in the 90s. Later, working as a producer, she was inspired by the carefully kept archives at CNN and CBS and began calling up old acquaintances to see what they might unearth. “A lot of these contact sheets were tucked away in shoe boxes or tucked away in the back of closets or in basements,” Tobak said.

Also, many early photos from the 80s were unpublished, because “a lot of the photographers weren’t professionals [at the time]. They just loved [hip-hop] culture or were a part of the culture, just like the artists,” Tobak added.

Tobak discovered Biggie’s very first photoshoot when she called photographer George DuBose looking for images of Big Daddy Kane. DuBose told her an incredible story about the time he trekked to Bed-Stuy in 1992 to photograph Biggie Smalls, a then-unknown rapper, for a collage of various artists printed on the back of a 12” record. The blown-up photo of Biggie featured in Contact High is electric. The artist points to street signs on the corner of Bedford and Quincy in Brooklyn, while friends spontaneously swarm the shoot and bring out a huge gun (that eventually scared off the photographer). It’s clear from the image, the authentic energy that launched Biggie’s career was in full force.

The book provides a broader view of hip-hop’s trajectory, making it easy to see artists’ development over time and track stylistic and aesthetic trends. “I tried to show a lot of firsts in the book,” Tobak says. “So I have Biggie’s first photo shoot, Jay’s first photo shoot, and then showing them again in the book sort of mid-career, and then later. You can see in the earlier photos they’re still kind of figuring out what their image is. Are they going to be tough or esoteric, this or that?”

One of the more striking themes that surfaces in the book is hip-hop’s attitude towards male sexuality and aggression. By the early 90s, hip-hop was associated with assertive vulgarity, but Contact High complicates the narrative. Photos from the 80s show edginess slowly creeping in. There’s an early photo of music journalist Bill Adler with a group of young, unnamed rappers. The photographer told the group to say “sex” instead of “cheese,” according to Adler, and since he was still a virgin, it made him light up with a smirk for the picture.

By the time male bravado was on full display, like in a 1989 press photo of Slick Rick where he’s fully grabbing his crotch, aggressive masculinity still wasn’t the whole story. There were strikingly vulnerable shoots happening throughout hip-hop’s most aggressive years, like Goodie Mob’s 1995 cover for Rap Pages magazine, depicting the four men wading shirtless in water, like a baptism.

Contact sheets of multiple shots from the same session reveal the sides of their personality some hip-hop stars kept hidden from the public. In that regard, a 1996 shoot for Vibe with Biggie and Faith Evans stands out. The final shot is tough and mobster-esque. But in the pictures that didn’t make the cut, the duo smiles sweetly while looking into each other’s eyes.

Even some old shoots that seem definitively misogynistic by today’s standards have complicated backstories. In 1995, Rap Pages magazine decided to recreate Janet Jackson’s 1993 Rolling Stone cover where a pair of male hands held her breasts from behind, but using Old Dirty Bastard and a model. But on set, when it came time to shoot, ODB asked onlookers to leave. He seems noticeably uncomfortable in the outtakes.

Though rappers are stereotyped as flashy or superficial, many photographers and artists were pushing for more cinematic or minimalist imagery. Sometimes it was photographers who’d put their foot down, like when Jason Keeling refused to let LL Cool J take his shirt off for a cover photo for YSB Magazine because he wanted to capture him as an artist and not a sex symbol, or when fine art photographer Barron Claiborne ignored P Diddy’s protests that Biggie would look like the Burger King as opposed to the King of New York when he captured the simple, iconic close-up portrait of the rapper wearing a plastic crown. Biggie died three days later, and the image became his most recognizable photo. But some artists were also clearly entranced by the cinematic lure of the medium, like Wu Tang Clan relying on photos to bring their kung fu fantasy to life, or Tupac becoming fascinated with antique large-format film cameras during his iconic Rolling Stone cover shoot.

Contact High also highlights the style evolutions of female rappers. In the early days of hip-hop, looks breaking from the norm made a big splash. In the 80s, Salt n Pepa’s iconic colorful Dapper Dan jackets were their personal clothes, because there were no stylists on those early shoots. That style suited them, but the vibrant, feminine aesthetic didn’t work for all MCs. Some women seemed constricted by the options of the time. When tomboy style with baggy denim and bandanas arrived, it was freeing. And the stylists who built this look, like Misa Hylton, became synonymous with hip-hop.

(Left) Salt n Pepa 1989 shot by Janette Beckman. (Right) Mary J Blige shot by Michael Benabib 1992. Reprinted from "Contact High." Copyright © 2018 by Vikki Tobak. Published by Clarkson Potter, an imprint of Penguin Random House, LLC

Contact High comes out at a time when institutions like Harvard, Cornell, and the Google Cultural Institute are thinking about how to archive hip-hop history. The book demonstrates the kind of mass reflection that is necessary to do the job justice. Tobak said that photographers have been reaching out to her on Instagram, sending her new contact sheets of things like Wu Tang’s first press photos and early portraits of Kendrick Lamar. Next April, the photos in Contact High will take on new life as an exhibition at the Annenberg Space for Photography in LA before traveling the country.

For contemporary photographers, the era encapsulated in Contact High represents a time when photo shoots were more spontaneous, controlled by fewer people. “It’s really hard for a young photographer today because they’re standing on the shoulders of all this imagery, and they’re dealing with a fast news cycle, and artists have become a lot more protective of their image,” Tobak says. “It’s not harder to get iconic photos, but it’s harder to get iconic authentic raw moments that aren’t over thought or overly planned.”

Tobak says she appreciates young photographers just shooting their friends and the simple things they find meaningful around them, and she hopes they don’t get discouraged if they’re not having a breakout moment. “For the people in this book, that was pretty much the same. It took over 40 years to understand what that moment was. So I would say don’t overthink it too much. Just follow your gut, and follow beauty, and follow what you think is important right now," she said. Perhaps the key takeaway of Contact High is that what may seem random today could show people a whole lot about this era in retrospect.

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