kay slay with leather jacket
Photo Credit: Johnny Nunez/Wire Image

DJ Kay Slay’s Story is the Story of Hip-Hop

On the eve of his birthday, the late DJ Kay Slay was honored with a street in East Harlem. We take a look back at how the New York City legend went from being graff writer Dez to one of the most prominent bootleging DJs in hip-hop.

It’s 11 am, August 13th, 2023 and we are here, amidst the El Barrio chaparral; untamed dry grass ornamented with discarded bodega snack wrappers and empty domestic beer bottles. There is no stage, so we are a modest disorganized crowd that didn’t necessitate a road closure, clustered on a corner, spilling onto the avenue in the shadow of the twin towers of the East River and Woodrow Wilson project buildings, and in spite of the fact that he's been dead for over a year, the mythic graffiti writer Dez is getting up one last time.

The piece is far smaller than the wild styles he once covered trains and walls with here, in this neighborhood, in these projects where he was born, raised, and fell in love with the culture that would consume him. Approximately a few inches tall and a foot long, it’s a fluorescent green rectangle sandwiched between the splayed street signs for E. 105th St. and 1st Ave. on a light pole at the southeast corner of the intersection that reads one of his many names: “DJ Kay Slay Way,” in white letters. Dez was known among the writers he ran with as an adolescent in these uptown subway tunnels and in the 3 Train yard in the late ‘70s and early ‘80s for his ability to maintain an uncommonly straight line. He was a clean and precise artist, so you’d imagine, if he was here, he’d be proud of this symmetrical machine printed work.

The sign is attached with screws and bolts, over a dozen feet in the air, posted by the department of transportation workers Dez used to run from, as part of a sanctioned public ceremony covered by several local news outlets and overseen by an NYPD battalion. Today, Dez has attained every graffiti artists’ holy grail since the modern conception of the artform came to New York in the late ‘60s, slightly before hip-hop itself. No chemicals will wash his name away, no toys will go over it. It is antithetical to the nature of graffiti itself, but here, in broad daylight, at the end of his long and unlikely lifetime journey through hip-hop, Dez has achieved immortality. He has finally thrown up a piece that will last forever. As part of the ceremony, Kay Slay’s great discovery, pupil, and avatar for the rap he loved, Papoose, grabs the mic and says, “They name streets and bridges after certain individuals, as a sign of the times. So when we go down Malcolm X Boulevard we know our brother Malcolm was once here. You go over that GW, you know he was once here. Frederick Douglass Boulevard, and so forth. Now, when they come to the Eastside of Harlem, they’re going to know the Drama King was once here.”

The many lives of Kay Slay

If you subscribe to “The Great Man Theory” of history — that we can understand times and places through the lens of significant actors whose experiences and contributions explain these eras — you could do worse than understanding hip-hop through Keith Grayson. Nearly to the (contested) exact day, born August 14th 1966, he was only seven years older than the culture, which spawned walking distance from his apartment. As an 11 year old DJ and eventual graff writer, he lived the culture fully, risking his life and freedom for each piece he threw up, spending his freetime and his passion on his art. He rubbed elbows with Debbie Harry and Keith Haring, was actually friends with Rammellzee and Fab 5 Freddy. He freestyled. He would hang out downtown at the Roxy, Danceteria and the Mudd Club. Late in life, Keith would explain the era succinctly: “When we started doing hip-hop, we didn’t even know it was hip hop. We didn’t have a name for it. It was something we did to take our minds off the fact that we were fucked up.”

Like it was for much of New York’s hip-hop community, the late ‘80s sucked for Keith, under the heel of President Ronald Reagan and New York Mayor Ed Koch. He had become disenchanted with the life and limb threatening pursuit of beautiful, labor-intensive temporal murals and turned to drugs, smoking dust, and selling crack. He was a self described shitty drug dealer, so it’s no surprise he was soon caught and did an eight month bid in Rikers Island, followed by a 14 month stint in an outpatient clinic where he dried out, got his life together, and eventually worked with HIV and AIDS patients.

But the music never left him. Just like he once tagged “Spade,”then “Zel,” before settling on “Dez,” Keith Grayson called himself DJ Kay Gee, but Naughty by Nature had a Kay Gee, so eventually he settled on Kay Slay. He began making blend tapes with DJ DEMO in the mid ‘90s, a once popular variant of mixtape, remixing the hits of the day with acapellas laid over surprising but well paired instrumentals. But in the late ‘90s, the DJ became less a technical talent and more a curator and personality. DJ Clue was the most notable and visible, known for getting exclusive freestyles and unreleased songs or cutting room floor tracks with Clue serving as a host and narrator. Kay Slay saw the game changing, and as he did so many times throughout his life and career, he adapted.

At the height of the Bad Boy dynasty, Puff Daddy’s vision of radio friendly pop rap had conquered the world. DJ Clue was a master arranger, but his tastes were more aligned with Puff’s, he had Ma$e rapping over a “Genius of Love” flip on his first label released album and a “William” nickname with JAY-Z and Rocafella.

Jerrod “General” Whittaker, Kay Slay’s longtime friend and manager, told me:

“[Kay Slay] actually had the street background, and the true authentic street connection that a lot of these guys didn't. So I would say he solidified that vein of the more edgier, street certified element of hip hop.”

Kay Slay was a counterweight on the mixtape scene, bringing back decidedly non-commercial rap. As the rapper and close friend of Kay Slay, Sauce Money told me, “He was a voice for the voiceless — specifically the MCs who couldn’t get a deal."

His voice couldn’t have better represented his persona as a DJ: coarse, authentic, aurally. It’s noisy hostility that evokes one of his many bulletproof thick leathers thick and untied Timbs, the uniform for Slay and his many soldiers aughts. Jarrod described the abrasive charm, the Mike Breen-like persona Kay Slay assumed on wax:

“It’s akin to being in a barbershop and hearing 'Ether' [which he premiered] for the first time. And everyone will be like, 'you hear that? Run that back?' That was his personality. So when he's dropping the running commentary like, 'Ah, MAN!,' is somebody saying something crazy? He's the fan in the moment, and it accentuated it for the audience, it’s a stamp of approval: if Kay Slay is dropping the ad-lib there, it must be fire. Funkmaster Flex is known for dropping bombs. Clue has his Desert Storm drops, but Kay Slay was the tough guy that loves hip hop and lives on the fifth floor in your building. That was just his personality.”

Bootlegging, the sixth element of hip-hop

It was a time when beef was in the air in New York. Artists, perhaps aware the formula was turning stale with the rise of the South, started attacking each other for the attention and airspace their music was no longer warranting. Slay understood this atmosphere. New York is an economy of struggle, thriving in the face of a number of adversities and competitors, always at war with other graff crews or rappers or DJs, clear eyed about the Darwinian mandate that in a city, an industry, a culture with limited resources and limited space, you have to fight for your own, and if necessary, take it from someone else.

During Kay Slay’s eulogy at the Apollo last year, Papoose revealed his friend and mentor used to regularly quiz him on the five elements of hip-hop. So let’s go over them: graffiti, DJing, break dancing, MCing, and — depending on who you ask — beatboxing or knowledge. Here, on the 50th birthday of the artform, I’d like to nominate a sixth element: Bootlegging. Theft has always played a role in the history of a medium practically invented as an act of reclamation, and in fact is a fundamental aspect of many of the existing elements. It’s the essence of the world remaking power of hip-hop, the idea that you — a Black or Brown Bronx teenager in the early 70s- oppressed, written off and caged like few groups of people ever have been in American history — can still seize your narrative, the Valjeanian impulse to take shit you need when you don’t have it. You steal electricity from hacked light poles to power your turntables and speakers. You steal records from the shop and you steal cans from the hardware store when you don’t have money to buy them. You steal IP from other artists when you flip their breakbeats as source material when you don’t have money to clear them. You steal advertising space on public walls and trains until the entire world is familiar with your art and knows your name.

Kay Slay, once again, described himself as a shitty thief, going back to his days as a writer. He was awkward and self conscious, couldn’t get away with stealing the spray paint cans he needed from a store. But when he didn’t have them, he would hang out in the 3 line yard with a baseball bat (as captured by the great Martha Cooper) waiting for a toy to cross his path, who he would bully out of their stash. I will take liberties and say Kay Slay was also a shitty kibbitzer. He was hard headed, he could be an unpopular gruff who wouldn’t kiss corporate ass or work on someone else’s schedule to make connections. “He was relentless,” Sauce Money said. “And a lot of times he would run the risk of rubbing the bigger guys the wrong way because he was so interconnected with the underdogs.”

So he didn’t have a cozy relationship with label heads and A&Rs who would slip his rivals choice records that cohered with their release schedules to generate some heat on the mixtape scene, without giving away too much. But Slay was smart, resourceful, and driven. He may have been a shitty thief, but he was a great bootlegger. He couldn’t get the records he needed legitimately, so as he once did in the train yard, he stole from the rich for himself. At every label during that era, armies of dissatisfied interns were unpaid and worked long hours. Slay developed plants at every outlet, serving as his plugs. He’d pay them the money Def Jam or Tommy Boy or wherever wouldn’t for unreleased heat, and in the dying days of physical media, he made a name for himself and found a niche.

DJ Kay Slay vs DJ Clue (Full 20 Minute Argument)

Within the illicit resold market of the mixtape, Kay Slay’s was the purest form of the concept: The most black market, a true enemy and affront to the system. He was a disruptor, partially because the game needed an alternative, and probably partially to piss powerful people off. This is how he became the “Drama King” who would “Slap ya favorite DJ,” (which he actually did.) When rappers wanted to do something stupid and potentially unpopular, that could hurt their earning potential or status in the major label system their A&R would talk them out of if given the chance, Kay Slay was there to provide a platform, to keep it real and get some shit you simply had to off your chest. You could go to Clue or Flex with your next single to generate some heat. You’d go to Slay with your diss track. It was pirate radio and art therapy, underground and uncut. He only extended this concept through the artist driven mixtapes he was a part of innovating with fellow Harlemites Cam’ron and his Dipset crew, circumnavigating the system and turning mixtapes into albums and albums into mixtapes.

Maturing into an elder statesman,

In the 2010s, tech killed the mixtape. The FBI, The Blog Era, and probably most of all, streaming ended that iteration of the black market music industry. But Slay never left the culture, holding down his Thursday night slot at Hot 97 till the end of his life. As he settled into this new phase in his career, his audience began to see a side of him that was always there, but wasn’t always obvious during his mixtape run. As Papoose said at his memorial service last year, “Slay was the reason for a lot of beef getting squashed. Ironically he became the voice of reason… He was all about unity. If you look at songs like “[Rolling 110 Deep] “[Rolling 200 Deep],” he’s the only one creating tracks like that, unifying MCs.” He had matured into the elder statesman, mellow in his interviews, introspective and diplomatic, not out of fear or softening, but you got the sense, because he realized it was no longer necessary. It was a position many of us would’ve loved to see him maintain for decades to come.

In high school, there was a joke my friends and I would make as we were getting high driving around listening to Streetsweeper tapes. The way the collective mixtapes of this era were oriented is you’d have your big ticket, headline grabbing names and tracks at the front, then the back five or six tracks were the equivalent of Saturday Night Live’s 10-1 skits: A place for the obscure and strange, the names struggling to garner a following and eventually earn a spot at the top of the tape. In some senses it was the Streetsweeper project in its purest form, the concentrated unvarnished idea of what he was getting at. Some of those MCs rose out of obscurity to carve out a career in what was a brutal landscape for New York rappers trying to stand out in the early 2000s, and some never did. Even in a mixtape industry of aspiring artists and also-rans, Slay’s cast of characters were uniquely, willfully stubborn and backward looking.

We would use “The Back of a Slay Tape” as a derogatory condemnation, slander for a rapper we didn’t think had it, dismissing talent that — for all our wisdom as dickhead teenagers — we deemed less than. Maybe there was a bigtime rapper’s protege the artist was trying to get on, or a suspiciously industry pushed rapper who put out a single that was making a little street noise. We’d say he sounded like his fate was eventually slotting into track 17 on Streetsweepers, Volume 25 — condemning them to careers in the shadow. I’ll stand on it today as a good bit, but I think about it differently now.

Kay Slay’s religion was hip-hop, a cliche that was true for him in the way it was for few others who make the same claim. He followed a militant, dogmatic, ultra-orthodox sect of the big tent faith and he was a true believer. The New York varietal of mixtape rap, skeletal, grating production stripped to its bone, with no catchy hooks or fat samples to lean on, gives you nowhere to hide. It’s set up and punchline, a brutal proving ground that relies on pure pen, flow and charisma.

It’s a descendent of rap in its purest form, the type that Keith Grayson would hear in the clubs and park jams he’d attend, and the trainyard ciphers he’d join at the very inception of the art. Yes, this was Papoose and Sauce Money and Duke Da God, but more importantly it was Ice Shuler, Grafh, the A-Team. They weren’t on Slay’s tapes because he wanted to grow his clout as a tastemaker. It was because he believed in them as practitioners, in the true disciples, and more importantly, in a culture that was clearly changing, he believed in the music they made: the ugly, angry, uncompromising, beautiful and fading ancient art that defined his entire life.


Flatbush local, culture writer, former mayor of New York City.