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Why They All Believe in Lenny Santiago — Including Hova Himself


The entertainment executive, photographer, and TV host speaks about how he blesses his diverse projects and passions

UpRising: You’re a man who’s worn many hats over the course of a long career in entertainment; the latest is hosting the Prime Video special Hip Hop World. How did this production come together and what was it like being in front of the camera for a change?

Lenny S.: It was great. I prefer to be behind the scenes as I've been for the last three decades, whether it’s photography, A&Ring, promotion, [or being a] music executive in general. I believe I was put on this earth to help others make their dreams come true. And I love that role. So for something like this, which is not the norm, I thought it was cool. It wasn't the intention at first. My partner Jason [Offor] and I were shopping a show that was a take on Anthony Bourdain, just mixing hip-hop culture and going to different countries abroad and seeing what the culture is like, whether music, food, or fashion.

Amazon and Live Nation said, “We would love for you to host it as opposed to just produce it.” That's how it happened. At first, I was a little reluctant. But my close friends and family said it's something I should jump on into. What makes the show pretty cool [is] I have this natural mutual respect from my peers in the music business. They trust where I'm going to take them, the questions I'm going to ask, how I'm going to make them look on camera. That's important. We need that in hip-hop. We have shows out there that are—let’s just say not as positive. I wanted to put something out there that showed all the things that I love—music, travel, food, fun, everything—just walled up in one in the name of hip-hop.

That rapport comes through in your interactions with DJ Khaled and Lola Brooke, who star in Hip Hop World and show some real personality.

Exactly. Khaled's been going to Jamaica since he was a teenager. That’s how he's developed these incredible relationships with Buju Banton, Capleton, and Usain Bolt. He wanted to show me all of those things. Lola wanted to go to a place she'd never been to. We took her to Paris and went to the good restaurants, a fashion house, and monuments for the touristy photos. We had a ball. It was cool seeing her with bright eyes, seeing everything for the first time.

Longtime music fans know you for your time as A&R at Roc-a-Fella Records, but newer fans might recognize you more for your photography. What initially made you want to pick up a camera?

My love for hip-hop made me want to get into photography. I was in awe of the rooms I was in and the people I was around. Prior to that, I would see photos of Malcolm X talking to Sam Cooke and Muhammad Ali back in the ’60s—photos of these figures who maybe weren't iconic yet, but you had that feeling they would be one day. That's the same feeling I had when I would be in the studio and there's an artist I work with named Jay-Z. Another artist that Ruff Ryders would bring to the studio; his name was DMX. All these different up-and-coming artists, semi-established producers, and music executives; in my eyes, these people were going to be the iconic legends. That's the reason I started taking photos... In hip-hop, nobody had videographers or photographers running with them like they do now. Not saying I discovered anything, but I was one of the early ones to notice this is something that needs to be documented. I was with Jay every day, so why not?

You’re curating that deep catalog of photos for a couple of special projects. Care to share what you’re working on?

Jay-Z has a publishing company through Random House called Roc Lit 101. I got two books coming through there: One will be The Gold Standard, a Polaroid book of my office, which has the gold couch. So it's everybody who's come through there. The other one is a 25-year behind-the-scenes photo book: Dressing rooms, studio sets, offices, vacations, weddings, and intimate moments of all the artists, athletes, or actors I've come across who have given me so much grace and allowed me to capture them. I don't have a title yet, but that's honestly my favorite one.

You also helped curate the new American Museum of Natural History installation, Ice Cold: An Exhibition of Hip-Hop Jewelry, which is giving chills to visitors in New York. Can you speak about your role? 

Of course. Vicki Toback is a good friend of mine and a brilliant writer. Ice Cold is her latest book—I had 10 photos in the book. She asked me to be on her board of advisors, which I was super complimented with. At this part of my life, that's where I'm trying to lean more towards: Being part of amazing projects, great boards, and things that make a difference. We set out to make one of the best hip-hop exhibits ever. And I think it's extremely important because the American Museum of Natural History doesn't normally have hip-hop in there. It's on the prestige level of the Louvre. It's a staple. It was an honor and a pleasure to help gather a lot of the pieces that were in the exhibit.

Was there a piece that you're especially proud you were able to help wrangle? 

Yeah, two pieces in particular: the Yamborghini piece [A$AP] Ferg gave us that belonged to his brother Yams, rest his soul. He was a pillar in hip-hop and an important part of A$AP Mob, so for Ferg to give us that piece was incredible. One of my other favorite pieces is the Ghostface eagle—that wasn't easy. You’ve got to understand, this exhibit runs for a year. We had artists letting go of some of their favorite pieces of jewelry for a year. It's not easy when they still use it during shows or photo shoots. So those two pieces stick out for me. There are so many other amazing pieces.

You're also involved in talent management. What's the day-to-day difference between managing a superstar like DJ Khaled versus someone who's not a household name?

They both take lots of hard work. The superstar side is obviously easier—you'll have more calls coming in that you get to manage and sift through while creating your own opportunities for the artist. With another artist who's not as exposed, you have to create those opportunities. But I encourage any manager or team to do it on both ends. As big as Khaled is, we still huddle every week, we put out goals for the next three years, strategic partnerships that we want. We think of these things and go out and pitch. Of course, we get turned down here and there. But a lot of times we don't. There's more grinding when it's a new artist or client. There’s more convincing, because only you, that artist, that artist’s label, that athlete's agent—only you guys believe in that man or woman.

You’re SVP at Roc Nation, an investor, and a business owner, among other hyphenates. Did you always see yourself as someone who would have this kind of multifaceted career? 

I did not see myself as what I am now. I just went to high school; I never got to go to college. I went straight into the music business, hands-on learning and interning. When I was an A&R, I was doing managerial duties for the artists that I was A&R’ing, not knowing those are management skills. I was doing what was a passion of mine. I used to A&R for Fabolous. When Jay was going out on tour, I was like, “Can Fab open for you?” Cool. Done. I’d go to this liquor brand and get a sponsorship... Somebody would shake me and be like, “Listen, you got them on the cover of a magazine, you got them two brand deals and a residency gig in Vegas—you're a fucking manager.”

Same with the book... Just because you didn't learn professional photography [and] don't know lighting doesn't mean you can't still capture the culture and publish that. I love that kids these days don't need any validation. They just go for it and achieve their goals way quicker. We were living with insecurities and fear of failure. That's really what it was. I never wanted to fail anybody that believed in me. So I didn't see those things, but I see them way more clearly now. 

Hip Hop World is now streaming on Prime Video. The special captures Lola Brooke creating the original track “Touch Down in Paris,” which is exclusively available to stream via Amazon Music.


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