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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.”

We caught up with photographer Michael Benabib to talk about the time Sean “Diddy” Combs rented Cher’s Miami house for a photo shoot…

Miami, 1997

The photo recalls a specific moment in hip hop history when, in the 1990s Bad Boy Records dominated the hip hop music industry. A portrait of an emerging kingmaker and his kings. Sean “Diddy” Combs, then known as Puff Daddy or Puffy or just Puff, was yet to become the music mogul that he is today but he was in fact already a force of nature. In just a few years, he went from being an intern at Uptown Records to launching Bad Boy Records in 1993 giving the world greats like Mary J. Blige, Craig Mack, Faith Evans and of course the Notorious B.I.G.

Now it was time to work the visual vernacular for his own debut work. Puff Daddy and the Family released their debut album, No Way Out on July 1, 1997. It was the apex of a moment in hip hop. Diddy chose Michael Benabib to photograph the cover.

“By this time I had known Puffy for five years. I met him during that infamous time when he was an intern at uptown records shaking it up,” recalls Benabib, a native New Yorker. “I was the unofficial staff photographer for Uptown records so I met Puffy when he was just an intern there. I would see him on video sets, in clubs, everywhere – he was involved in everything. He was so enterprising.”

That enterprising spirit and zero fucks attitude would serve Sean Combs well. “To stand out in that music crowd of the 90’s, you had to be charismatic and you had to be relentless in your vision. It was really a special time.He would often have me do shoots at 2am. Puffy would work all night and then want to do a photo shoot afterwards. He was always on.”

Benabib, along with legendary stylist Groovy Lew were flown out to Miami to shoot a series of publicity photos for the Bad Boy label, one of which ended up being the album cover for the 17-track project produced by Combs and the production outfit, The Hitmen, and featuring guest spots from The Notorious B.I.G., Mase, Faith Evans, 112, Black Rob, The Lox, Lil’ Kim, Busta Rhymes and Jay Z. Combs was half way through creating the album when Notorious B.I.G., was shot to death March 9, 1997. In tribute, “I’ll Be Missing You” was one of the lead singles from the album and was again a highlight when, celebrating over 20 years in the industry, Combs recently reunited all of his 1990’s Bad Boy artists for a reunion at the 2015 BET Awards.

Recently, many of Benabib’s photos of the early days of hip-hop were acquired by the Smithsonian Institution’s National Museum of African American History and Culture as part of the acquisition of The Eyejammie Hip-Hop collection, made up of 400 photographs, collected over the years by historian and former Def Jam Recordings publicity director Bill Adler (*salute Bill Adler for collecting these images over the years!).

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The Shoot

Michael Benabib: I had flown down with Groovy Lew, Puffy’s stylist from New York for the three day shoot. There was definitely an entourage. I remember it was Super Bowl weekend in Miami. When we all went out to dinner it was a motorcade of SUVs. On the flight all the clothes and the photography equipment went missing. Much drama ensued. The next day all the equipment and clothing arrived. The shoot lasted over three day weekend. At any given time the house that puffy had rented had 10 to 20 people in it. I was told that the house belonged to Cher. There was 100 foot yacht docked adjacent to the house for our use. The scene at the house was alot of weed smoking, a lot of beautiful women—basically lifestyles of the rich and famous. Puffy would go upstairs, up this circular staircase and disappear for a bit and then come down and be like ‘ok playboy, let’s do this.’

The Shot

My style is “let’s go for a walk and see what happens” but with so many people on this shoot, I couldn’t really be so free-form about it. Puffy and Groovy Lew had a vision for what it would look like and since there were six people on the cover, I had to shoot alot to get the one image where they all looked the way they wanted. And where they were all looking at the camera. I usually don’t do alot of prep. I like to just let the magic happen. But to get this shot, I really had to focus. I had never seen the house before. I never saw the clothes. Jadakiss, Mase..they were all in the photo and getting the single perfect shot was a challenge.

The Camera Nerd Out

Hasselblad with Tri-X film. In the age of CD covers which were square, the Hasselblad square format was perfect.

The Q+A

The National Museum of African American History and Culture recently acquired your work. That must feel amazing and important given that you were shooting hip hop at a time when perhaps you couldn’t imagine all this.


I am absolutely thrilled! I can’t wait to visit the museum. It’s about time that this museum was created and that African American culture was celebrated and honored in this way. Having hip hop photography as part of their collection is significant. Bill Adler approached me when they started to discuss the acquisition and asked if I would want to be included. I of course said yes. I was the first solo show at Bill’s Eyejammiegallery and I am just so pleased to be part of something so historic.


You met Puffy very early in his career. Did you get the sense right from the beginning that he was so visionary in knowing exactly the visuals he wanted and translating the sound and a vibe into a visual strategy?

I have shot a lot of artists over the years and most of them, when asked about how they want to be portrayed, just say ‘I want this shit hype. I want this to be on the next level,’ and I’m like what does that mean? Puffy was different. He knows exactly what he wants and he has the ability to get it across to the people he works with. He envisions on a deeper level. When Puffy hired me to shoot Usher’s first album cover, for example, he completely had a plan of what the visuals would convey.

Groovey Lew was the stylist on this shoot and, at the time, came in the game under Sean “Diddy” Combs’ Bad Boy Entertainment movement in the days of the company’s formation.

Groovey Lew is a professional. He knows how to give artists a look that is genuine and very much cool and authentic. The way an artist dresses is such a personal thing and he knows how to tap into that. The clothes in the shoot speak to Puffy as being a mogul. They (Puffy and the Bad Boy artists) had an awareness of who they were and what they were going to become. And they had a keen awareness of the role visuals played in all of that.

There were so many people in the photo. Talk about the group dynamic that day and how you were able to capture a shot where everyone was on point.
There were six people in this shot. You have to shoot alot You can see in the contact sheet t. Sometimes I shoot even knowing that the image is not right. When you shoot alot, you make the subject more relaxed.. I fire off a few shots just to let the subject know ‘OK, it’s we go..”
What was it like to be part of the entourage for those 3 days of shooting?
I felt like I was in the Presidential motorcade — A line of 8 SUVs going through traffic.

Everybody was really enjoying themselves.

Follow Michael Benabib on his website and Instagram.

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 website, Facebook, Instagram, or Twitter for more info.