On September 29, 1998 some of Hip-Hop's greatest artists gathered to recreate an iconic photo. The photo is a re-creation of fashion photographer Art Kane's historic 1958 A Great Day In Harlem, which assembled 57 of jazz music's greatest musicians. The image, shot at 17 East 126th Street was featured in the January '59 issue of Esquire Magazine and included images of Dizzy Gillespie, Charles Mingus, Thelonious Monk, Art Blakey, Count Basie, and more.

Four decades later XXL editor in chief Sheena Lester commissioned A Great Day in Hip-Hop, which was shot by legendary photographer Gordon Parks, and featured 177 artists including Busta Rhymes, Public Enemy, Rakim, Fat Joe, The Wu-Tang Clan, Reverend Run, Slick Rick, Da Brat, and more. The photo became the largest gathering of musicians in a single image in history.

Hip-Hop's Greatest Day features shots by co-founder, and then XXL publisher Jonathan Rheingold, editor Ben Osborne, and Parks protégé, Johanna Fore. Rheingold said in a statement, "[I made it a] mission to identify folks who were snap­ping photos on 126th street that day and developed the largest archive of behind-the-scenes photos documenting that great day.”

Noting that Gordon Parks may not have been a Hip-Hop fan, he added, "he understood the importance of this opportunity. And Sheena Lester, who was the editor-in-chief at the time, really convinced him that there was really no other photographer that one could possibly think of that would be more suitable to capture such an amazing moment than him, and he took it on.” Rheingold also has a five part audio series planned to celebrate the iconic day.