DJ Kay Slay, a longtime fixture of the New York rap world, has died. The New York Post reports that Kay Slay died yesterday after a four-month battle with COVID-19. Kay Slay was 55.

Born Keith Grayson in East Harlem, Kay Slay started out as a teenage graffiti writer, and he appeared in the famous 1983 documentary Style Wars. In the late ’80s, Kay Slay spent a few years in jail, and he reinvented himself as a DJ after getting out. Kay Slay started out releasing mixtapes in the ’90s. He eventually signed with Columbia and released his album The Streetsweeper, Vol. 1, a sort of major-label approximation of a compilation mixtape, in 2003.

Kay Slay continued to released major-label albums, but he also maintained his place in the underground-mixtape world all through the ’00s. Kay Slay was known as the “Drama King,” and his tapes typically featured a whole lot of shit-talk — from the featured rappers, but also from Kay Slay himself. At various points, Kay Slay feuded bitterly with rap titans like Jay-Z and Nas. He also mentored New York rappers like Papoose. He released The Soul Controller, his last album, in December of 2021. That same month, Kay Slay was hospitalized with COVID, and he was put on a ventilator.

Below, listen to some of the most notable tracks from Kay Slay compilations.