DJ Kay Slay evolved with hip-hop, and hip-hop evolved with him

“He used to be the King of the 3 Line, but now he's the DRAMA KING!”—a YouTube comment from 11 years ago

Over this past weekend, Keith Grayson, the Harlem native best known to hip-hop fans as DJ Kay Slay, died following a months-long battle with COVID-19. He was 55 years old. Famous — and infamous — for the deluge of mixtapes he hosted across three decades, which helped break new artists and served as neutral venues for feuding superstars, Grayson could trace his involvement in hip-hop from the genre’s beginnings in the late 1970s through its commercial breakthrough and dispersal onto the internet. In keeping with its spirit, his life and career are marked by reinvention and a persistent will.

Grayson was raised in Spanish Harlem’s East River housing projects. He turned 7 years old the week of DJ Kool Herc’s storied back-to-school party at 1520 Sedgwick Avenue in the Bronx, widely considered to be hip-hop’s big bang; when he was not much older, Grayson began taking the train North to that borough to see Afrika Bambaataa and the Zulu Nation play at the Bronx River Center houses. He was enamored with the music, but would find his way into the culture through the graffiti-writing scene that exploded across the city. By 1978, he was practicing in the schoolyard. A year later, his work was up on the interiors of the 6 train.

Under the name Dez, he began tagging and building more elaborate pieces on the walls of buildings and — crucially — on the subway cars idling in railyards after hours. There’s a famous scene in Style Wars, the 1983 hip-hop documentary that centers on graffiti, where the artist Skeme recounts his activities the night before: emblazoning the words CRIME IN THE CITY across an entire segment of the train. The dialogue of this scene, which was sampled at the beginning of Black Star’s “Respiration,” hears Skeme credit his collaborators; one of them is Dez. In a separate interview for the same documentary, Grayson explains the appeal of writing, which often had to be done under the cover of night and with the threat of arrest hanging over it. “It feels good when you pay your fare or hop the [turnstile] and walk down the stairs, and then, whatever train pulls into the station, you see your name in big, bold, bright colors,” he says. “It makes you feel good. You’re telling the world: I am somebody.”

To the extent that graffiti was competitive, the stakes at first were mostly bragging rights. But there soon proved to be money in it — if not for the writers themselves. Gallerists in SoHo enlisted kids to make canvases which those gallerists would then sell to European collectors for many thousands of dollars. When they returned, they might give the artists a couple hundred. This extractive economy, which echoed various types of colonial trade markets dating back centuries, combined with Ed Koch’s citywide crackdown, soured Grayson on graffiti.

By the end of the ‘80s, he had followed many of hip-hop’s early principles to the Disco Fever, the South Bronx nightclub that was then a hub for the culture. He started using drugs heavily, and then peddling them; he also resorted to doing stickups to make financial ends meet. In 1989, Grayson was convicted of possession with intent to sell and served almost a year on Rikers Island. When he got out, he got sober and, aiming to be of service in some way, began working at a Bronx facility for HIV and AIDS patients.

But Grayson still had the itch to be involved in hip-hop. Hoping to break in as a DJ, he went to acquaintances from the drug trade, asking for the capital to buy equipment and records. They balked. The rejection would be mirrored a half-decade later when Grayson, who had by then established himself as a mixtape DJ with a not-insignificant following, found himself shut out of the music industry’s official channels. Instead of taking these rebuffs quietly, he fired back, cursing out executives by name in between freestyles and exclusive songs. He had already redubbed himself Kay Slay, but this was the moment when Grayson earned his more precise moniker: The Drama King.

This ethos made some Kay Slay tapes controversial, though he was for the most part seen as an honest broker. It was not unusual for two warring rappers to have their diss songs included back-to-back on the same tape, or on consecutive volumes. (Grayson did not subscribe to any theory of scarcity, or even one of careful canonization, as with DJ Drama’s Gangsta Grillz series. His tapes came in a cavalcade.) In 2001, it was a Kay Slay tape where Nas premiered “Ether,” the song that gave him an unlikely comeback victory in his feud with Jay-Z and penetrated the culture so deeply that its title is now shorthand for the knockout punch in a battle. But it was arguably not even the most scathing Jay diss to make a Kay Slay tape.

In 2000, Grayson put out a tape hosted by Alberto “Alpo” Martinez, his fellow Spanish Harlem native who became one of New York’s most notorious drug dealers. By the time the tape came out, Alpo had been in federal prison for nearly a decade; his monologues throughout the record constituted his only public interview to date. If that weren’t shocking enough, Grayson included an interlude from Velma Porter, whose son Rich had been murdered by Martinez. But Ms. Porter was not interested in litigating the killing — she took aim instead at Jay, who had begun likening himself to Rich Porter in his rhymes. Adopting Jay’s flow from his single “Do It Again,” Ms. Porter taunts him: “You got a lot of drops, lots of Bent-a-leys/But none of that shit don’t make you R.P.”

Grayson’s project was bigger than beef. He had an ear for talent, and while he would collaborate with artists from around the country and across a variety of rap’s subgenres, he was one of the key boosters for a certain kind of muscular, verbose New York rap. To wit: He hosted the first Dipset mixtape. But this can be most clearly seen in Papoose, the artist he helped turn into one of the most sought-after young talents in the industry even as his style was falling far out of vogue relative to the Southern rappers who dominated the 2000s on radio and television.

While there would eventually be two Kay Slay albums on major labels, Grayson’s life can in many ways be seen as a celebration of hip-hop’s tantalizingly ephemeral nature. From the graffiti work that was criminalized and whitewashed by the city to the mixtapes that were disowned by corporations and targeted by the government, he trafficked in what could be loved and studied at the moment, but never pinned down for too long. This is even reflected in his 20 years as a host on Hot 97. There were no links to forward or white labels to pass from hand to hand when something unexpected happened on his airwaves — just frantic calls to turn on Kay Slay.

The insufficiency of any tangible resume meant Grayson had to work twice as hard as his contemporaries in other mediums to cement a legacy. “I never go and do one piece and leave,” he said during his Style Wars interview, about sneaking into railyards after dark. “If you’re gonna go, you go out to bomb. You do four, five cars in one night. That’s what shows a king.”