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In our series, Contact High: The Stories Behind Hip Hop’s Most Iconic Photographs, writer Vikki Tobak talks with those who have played critical roles in shaping hip hop imagery. They offer a rare glimpse of the creative process that went into the making of each photo.

Getting access to the original and unedited contact sheets, we see the “big picture” being created and can look look directly through the photographer’s lens. Photographers typically don’t show their contact sheets. They’re a visual diary. Film negatives on a roll of analog film allowed these photographers (and now us) to see the full range of images in order to develop the “money shot.”

In our latest installment, Jayson Keeling talks about the photo that made the ladies love Cool James – oh, and that time Slick Rick sold him a peacoat, but we digress…

New York, 1993

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Regrets, photographer Jayson Keeling has had a few. Like the time he didn’t let LL Cool J take his shirt off during a cover shoot for YSB magazine. Despite multiple requests from the ladies on set that day, Keeling thought a shirtless LL was too expected, cliché almost. He wanted to photograph the rapper in a bold, cinematic portrait. By the time LL walked through the door that day, he had already achieved mainstream success and was postered-up on many a bedroom wall as the hip hop era’s official heartthrob. You can bet in most of those posters, LL had his shirt off. Keeling opted instead for shadow and drama. LL, who was promoting 14 Shots to the Dome, the album coming on the heels of the hugely successful Mama Said Knock You Out (1990), wasn’t accustomed to hearing ‘no’ from the creatives that surrounded him, but he trusted Keeling and together they made a bold, singular portrait.

Raised between the Bronx and Jamaica, Keeling got the commission for now defunct YSB magazine (“Young Sisters and Brothers,” was the first national lifestyle magazine for African American youth and published by BET) during the early 1990s, a fertile time for hip hop magazine publishing.

Keeling now lives and works as an artist in Brooklyn, creating provocative work challenging politics of sex, gender, race, and religious norms much like the way he challenged the visual language of early hip hop imagery.

The Shoot

Jayson Keeling: This was for a YSB magazine cover in January, 1993. It was my second assignment. I didn’t know anything about LL personally at that point, and was quite new to taking photos. I had a close friend named Kingman Huie. We attended the High School of Art and Design together. This was like the hip hop high school. Everyone went there. Rock Steady guys went there, everyone…and we were all just starting to do creative things super young. So my friend got the commission for YSB first and then somehow put me on. I realized looking at these photos again recently just why and how LL became an actor. He brought so much generosity and openness to the photographers he worked with. He knew I was a new photographer and he was super patient with me.

The Shot

Image to image, LL would give these little nuances and gave a lot of gesture with purposeful power. He was brooding in some shots, playful in others, and some sexual. That of course was a big part of his persona at the time. The women on the set were all like, “get him to take his shirt off” and even he said “I wanna take my shirt off.” I insisted that he didn’t because it was expected. But I regret that now. I have regrets from most shoots I do and this was one of those moments.

The Camera Nerd Out

Hasselblad medium format TriX black and white. And I did polaroids. This was shot at Broome Street Studios.

The Q+A

This shot is really tightly composed and cinematic in the way it’s lit. What was your intention there?
There is a great confidence in this shoot, it’s pure shadows and volume. And I was using lights from the hardware store. 3 large bulbs, harsh and simple. The bulbs cast these amazing shadows. And LL even asked me ”why aren’t you using those lights that flash” and I was like “I don’t know how to use them.”

So style played a big part in what you were going for?
Style was a big part of everything back then. I think I was the first person to show up in the Bronx with doc martens and a black trench coat. My mother was livid but she got used to it.

Being of Jamaican descent growing up in the Bronx, how did you feel around identity and duality, being of both an immigrant and from around the way?
My parents wanted to move back to Jamaica at some point and we would go several times a year. My dad owned a small bodega in the South Bronx. Living in the Bronx, people kept telling me I had “the look,” but as soon as you open your mouth it doesn’t work. I was part of an immigrant family and I was negotiating this duality. My parents never lost touch with Jamaica and have homes in both places. My mom knew Slick Rick’s mom and she had organized a concert for Slick Rick in Jamaica.

Your mom seems like one cool lady. So you and Slick Rick had that connection?
Slick Rick sold me a peacoat, and he was pretty saavy. I remember, it was a grey peacoat. I don’t know if he found it or whatever (laughs). A few weeks later, He saw me in the street and he’s mocking me like, “mommy, do you like my coat?”

You seriously bought a peacoat from Slick Rick?
Yeah! Our families are really close. We called him Ricky. My dad owned the neighborhood Bodega, about 4 blocks from where we lived. Me and my brothers used to work there. Slick Rick’s sister worked there too. Both of our families are of Jamaican descent. Ricky’s cousin worked for my dad too, in construction.

Tell us about your career at the time this photo was taken and what artists/photogs/cultures inspired you early on?
I’m self-taught in my parents’ basement in the Bronx. I paid attention to photographers who shot cinematically… hollywood sculptural, film noir style.

What do you shoot on now? Do you still make contact sheets?
I still shoot 8×10 film if it calls for it with a Toyo View camera but I rarely make contact sheets.

You also have a vast archive of gorgeous shots of your time in Jamaica over the years. What do you plan to do with them?
I have documented my family in rural Jamaica. Specifically in Frankfield, a town in the parish of Clarendon in central Jamaica. I was really into drawing and architecture and that’s the feeling I wanted my photos to have. I definitely would like to do something with those photos, perhaps a book, as they capture a time and style that is beautifully Jamaican.


Follow Jayson Keeling on his: website and Twitter

The Contact High Project, conceived by Vikki Tobak and published exclusively on Mass Appeal, will culminate into a book and exhibition. Check out the Contact High websiteFacebookInstagram, or Twitter for more info.