After a monthslong battle with COVID-19, DJ Kay Slay — born Keith Grayson — passed away on Sunday (April 17) at the age of 55. A renowned graffiti artist who starred in 1983’s Wild Life documentary, and a mixtape maven who released his final project in December, it’s safe to say Kay Slay was a hip-hop renaissance man.
Whether he was patrolling the SiriusXM radio airwaves giving emerging artists a chance to freestyle, or launching Straight Stuntin Magazine to spotlight curvy Black women who weren’t getting booked for traditional modeling gigs, the self-proclaimed Drama King always represented NYC hip-hop culture to the fullest. Kay Slay refused to sacrifice his integrity for what might have been trendy at the time.
Over the course of his decorated career, the East Harlem native notched collaborations with artists ranging from Snoop Dogg to Power‘s Joseph Sikora. A pair of rap veterans who also forged close bonds with DJ Kay Slay from New York City to The Bay Area were Fat Joe and E-40.
40 and Joe’s relationship with Kay Slay dates back decades, with numerous collabs under their belts, and the two hip-hop lifers even kept in contact with the Drama King right up until his January hospitalization.
Billboard caught up with both E-40 and Joey Crack to recall their fondest memories of Kay Slay, and shed light on his legacy in hip-hop.
Billboard: What was your first introduction to Kay Slay?
Fat Joe: The first time I seen Kay Slay was in the  movie Wild Style. He was a legend in the graffiti world, which is our sub-culture. Most of the biggest artists you got out here now, they started out as graffiti artists, and then they graduated to selling these million-dollar pieces. Kay Slay could’ve easily turned into an artist where his pieces were worth millions of dollars.
E-40: I met Kay Slay in the mid-’90s, somewhere around ‘96 or ‘97. He was a real one. When I say a real one, I’m talking about somebody that don’t care about what the media or the industry says about a person. I was always the underdog, and Kay Slay didn’t care about no underdog s–t — he cared about what he liked, because he listened to it with an open mind.
Can you recall your last conversation with Kay Slay?
Fat Joe: I spoke to Kay Slay the night before he went into the coma. We both had COVID-19 at the same time, but mine didn’t hit me like it hit him. He was basically saying that it’s just so hard to breathe. This was the very beginning, like a couple of days in… He was like, “Yo this breathing shit is horrible.” Ultimately, I’m sure that’s what took him out because that’s what was giving him the most complications.
I told him I loved him and he told me he loved me, and I told him not to give up and keep fighting. He told me, “I’ll never give up.”
E-40: I had turned in my verse for his song before he had gone into the hospital. I had spoken to him too. We were talking about vaccination and stuff like that. He never thought that this would’ve hit him. He said he’d take herbs and sea moss – I think that stuff helps prevent it, but anybody can get this s–t.
It got him in the worst way. And I thought he’d pull through because he’s a strong-minded dude. He texted me that he was going through it, and his oxygen level was up so, I was really optimistic and that was encouraging to hear. He just hoped that it didn’t get to shut down his organs. And that’s what it did.
What’s a memory you have from working on music together?
Fat Joe: He got upset with me one time because I didn’t go to get on one of his tapes during COVID. This was when everyone was scared to come outside the house. He started cursing me out. Kay Slay can curse Fat Joe out — he’s got that card. He’ll call around to my closest guys and curse me out with them. They’ll call me back like, “Kay Slay’s pissed man.” He had that type of juice. When I put out “Sunshine Delight,” he hit me up: “I thought you wasn’t gonna be in no studio.” I said, “Slay, it’s a hit. Come on, man!”
We had a tremendous bond for years, and we’re gonna miss him and we’re gonna represent him as long as Fat Joe’s on earth. We’re gonna represent him the right way, as an icon and legend and gatekeeper for hip-hop culture.
E-40: I was on Rap City around 2003, and we had just pulled up to the video shoot and [host] Big Tigger was like, “We got the Drama King DJ Kay Slay in the house.” And I was freestyling in the vocal booth. Legendary Kay Slay — this is so sad, bro! It’s hard to believe, and it’s heavy on my heart, because he was such a good dude and legendary guy. Always positive and upbeat and he didn’t take life too seriously.
How would you sum up his legacy in hip-hop?
Fat Joe: He’s a king — and simultaneously, graffiti artists around the world are sending me tribute graffiti murals dedicated to Kay Slay. From L.A. to New York, he’s a Godfather of graffiti, and goes down in the books. Music-wise, Kay Slay — the best way to describe him is we lost the last guy on mainstream radio that would give the small up-and-coming artist a chance.
He was a die-hard New York boom-bap DJ, and even when drill is No. 1 or everything changes, you listen to Kay Slay and you’re just listening to nostalgia. When you on Kay Slay’s show, you heard them all with different players. He never changed with the times or act and he wanted to always rep NY hip-hop. A lot of people from all around the country really appreciated him for that. They appreciated his loyalty and his realness to the culture.
E-40: When it said, ‘Warning, the Drama King is in the building,’ that’s the dopest s–t ever. There’s nobody with an intro like that when they get on the turntables. I’m gonna miss that dude. He always kept it solid not salad. He had a great ear for music.
He’s one of my favorite DJs and one thing about him is he was unique. A big dude, wearing those glasses and he was always dressed fresh. He stuck to the script and was never into sucker s–t. He was the guy behind Straight Stuntin Magazine and would be funny on the internet. Overall, a raw dude — and he was older than me, so that was big bro.