How Sheena Lester Recreated One of Esquire's Most Iconic Photographs

"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links."

It's a beautiful, sunny morning on September 29, 1998. There are birds chirping. Children playing. Oh, what's that over there? Countless hip-hop legends gathering on a Harlem stoop, posing for a photograph—titled "A Great Day in Hip-Hop"—that will live forever in history. Side by side are Rakim, Slick Rick, DJ Jazzy Jeff, Busta Rhymes, Questlove, Common, and many, many more.

So, why did so many talented rappers convene that September day? You have to go back to 1958. For Esquire's January 1959 issue, photographer Art Kane shot a portrait of celebrated jazz musicians at 17 East 126th Street. Named "A Great Day in Harlem," the photograph includes the great Dizzy Gillespie, Art Blakey, Thelonius Monk, Charles Mingus, Count Basie, and more. 40 years later, XXL's then-Editor-in-Chief Sheena Lester set out to recreate the famous Esquire shoot—but with the 90's biggest names in hip-hop.

"The original image was just such an iconic piece of magazine history," Lester told Esquire. "The first thought I had about bringing hip-hop's finest to those steps—to help consecrate it where those jazz legends were—there's nothing about that that didn't curl my toes into pretzels." To her surprise, Gordon Parks, a legendary photographer and director, agreed to take the photo. That was all Lester needed—artists from around the country filled up the whole block. The result?

To reminisce on "A Great Day in Hip-Hop" for its 25th anniversary, Lester put together an Audible podcast called, The Greatest Day. It celebrates the story of how the photo came to life, from inception to print. The six-episode series, as told by Lester herself, also features testimonials from Black Thought of The Roots, MC Serch, Rah Digga, and more. On a high from the buzz of its release, Lester spoke with Esquire about what made the original Esquire photo so iconic—and why she sought out to recreate it for a new generation.

ESQUIRE: Why do you think everyone at XXL originally turned down the idea to recreate Art Kane's photo?

SHEENA LESTER: I think they just needed convincing. The original image was just a portrait of genius, in a way that captured the music and the magazine. It was too good of an idea to let go. I had already done an array of we thought it would be impossible magazine covers at Rap Pages. It just never occurred to me that a "no" was in the atmosphere. We were going to get that done.

Do you think the violence at the time—especially Biggie and Tupac's murders—played a part in making people hesitant?

Not at first. After talking to the team about it, they voiced their apprehension, but nobody voiced the possibly of violence. It wasn't a real concern. If we really thought it was a possibility, we wouldn't have done it to put anyone's life as risk. It was just too much love. We knew for sure that that thing would be hanging in museum walls for eternity once Gordon Parks was taking it. And so did the rappers. There was no way they weren't going to come.

SEE THE XXL IMAGE ON THE GORDON PARKS FOUNDATION'S WEBSITE

What did you say that finally convinced Gordon Parks to take the shot?

Once I told him that—for every reason in the world that really mattered, nobody else should take the picture but him—maybe he recognized the magic of it all. And almost a pseudo responsibility. He knew what he meant to the Black community—and arts and culture in general. So, once he was convinced that we weren't doing anything gimmicky, he said, "Yes." And once we were there, he got applauded. They came up to him as fans, just like they did to each other. It was such a love fest.

Who were you especially excited to see that day?

Rakim. Rakim will always be my favorite, and it was very cool to see everyone else be excited for him. And, frankly, The Roots. I was raising my kids in Philadelphia at the time, so seeing them was super exciting. Especially since I knew that Philadelphians would love that.

Were any collaborations born out of people connecting for the first time on that day?

It's funny, because E-40 was one of two people on the block that day with cellphones. You know, this was pre-cellphones. It was just him and Da Brat, and there's a shot we have of Tash from the Alkoholiks giving E-40 his digits. I'm going to see Tash this weekend, and I'm going to ask him because I would love to know that. There certainly were a lot of numbers exchanging and a lot of smiles.

[Editor's note: On "Rockin' With the Best," by the Alkoholiks, Tash raps, "'Cause to danger I'm no stranger, my mic has insurance/But just to keep it safe, I called E-40 for endurance."]

It seems like it really meant a lot for E-40 to show up as a West Coast representative.

Hell yes, absolutely. From both the West Coast and the Bay Area, it doesn't really get more authentic, genuine, or humble than E-40. It was great to see him out there. And we had Muggs from Cypress Hill. It was nice to see the West Coast artists get their love. It was such a mutual respect of fandom. Listening to the podcast, I had not even realized that so many of the artists were potentially anticipating drama, because of Pac and Big. But once everyone was out there, there was no aura of negativity anywhere.

Do you think—as we approach the 50th anniversary of hip-hop—that a photograph like this might be possible again?

I hope so. I would love to be able to see something like that. But I don't know if folks could keep a secret in this day and age. Gordon Parks is gone, and I don't know if there's another photographer who could command that kind of respect from a generation of artists the way that Gordon Parks could. That is really something that can't be duplicated.

You Might Also Like

• Kid Cudi Is All Right

• 16 Best Shoe Organizers For Storing and Displaying Your Kicks