Legendary New York rapper, producer, DJ, and beatboxer Biz Markie died peacefully at his Baltimore home on Friday (July 17) after reports over the past year of his failing health.

The 57-year-old Just a Friend hitmaker’s wife was by his side.

Markie, whose goofy antics and playful lyrics earned him the title the ‘Clown Prince of Hip-Hop’, started out in the early 1980s in New York City as a teenage beatboxer and rapper before joining the Queensbridge-based Juice Crew collective. As a member of the group, he worked alongside other hip-hop trailblazers like Marley Marl, Big Daddy Kane, and Roxanne Shanté.

Markie’s trademark beatboxing skills were both featured in and the subject of his 1986 debut single, Make the Music With Your Mouth, Biz. He released his debut album, Goin Off, on the Juice Crew’s label Cold Chillin’ Records two years later, featuring tracks like the popular Vapors and the goofball rap Pickin’ Boogers.

In 1989, Markie put out what would become his most successful album, The Biz Never Sleeps, which included the platinum-selling smash hit, Just a Friend, which featured an interpolation of the 1968 Freddie Scott song (You) Got What I Need.

His sampling of music would have an unplanned impact on the hip hop industry with the loss of a lawsuit which barred the distribution of his third album after it included uncleared samples, which had been a staple of the genre for years. It would be the beginning of the end of the unchecked sampling which had helped build the industry in its formative years.

Markie’s cause of death was not confirmed by his representative on Friday, but he had been fighting Type 2 diabetes over the past decade, and his health had reportedly taken a turn for the worse early last year.