In this episode of Gems with Shom, I sit down with Jay Stewart — music executive, DJ, exhibit curator, and founder of one of the most fascinating hip-hop artifact collections in the world: The Jay Stewart Collection.

Jay’s story begins in Queens, New York, growing up during the golden era of hip-hop and the early foundations of the culture. From there, he built a remarkable career across the music industry.

Jay worked as a promotional rep at Rawkus Records, helping break artists like Mos Def, Talib Kweli, and Big L, before moving into major label marketing roles at MCA, Geffen, Interscope, and Universal. Along the way, he helped promote albums from artists like Common, The Roots, Mary J. Blige, and Blink-182.

Over the years, he quietly built an incredible archive of rare hip-hop promotional posters, memorabilia, and artifacts — items that once lived in record stores, radio stations, and label offices during the golden era of physical music culture.

Today, that archive has become The Jay Stewart Collection, a traveling exhibit celebrating hip-hop’s visual and promotional history. Pieces from his collection have even appeared in the Sotheby’s Hip Hop Auction, placing these artifacts alongside fine art and cultural history.

In this conversation, we explore Jay’s journey through the music industry, the lost art of physical music promotion, and why preserving hip-hop’s visual history still matters today.

🎧 Drop a Gem On ’Em segment includes:
Kenny Burke • M.O.P. • Big L • Mos Def • MF DOOM • J Dilla • Tribe Called Quest • Prodigy & Alchemist • Kid Cudi • Nonchalant