The Diabolical Biz Markie, one of the greatest showmen in rap history, has died. Rolling Stone reports that the Biz died earlier today. No cause of death has been revealed, but Biz had a number of health issues, including type 2 diabetes. Last year, Biz suffered a stroke after going into a diabetic coma. In June, erroneous reports of his death circulated online. Biz Markie was 57.

Biz Markie was born Marcel Theo Hall in Harlem, and he grew up on Long Island. In the mid-’80s, Biz gained a reputation as a presence in New York nightclubs as a lunatic dancer and beatboxer. He joined up with Marley Marl’s Queensbridge-based Juice Crew, and he released the Marley-produced debut album Goin’ Off in 1988. On that album, Biz developed an image as a wild, unpredictable joker, a truly fun presence.

Biz was one of the producers on his sophomore album, 1989’s The Biz Never Sleeps, and it featured the loopy, unhinged classic “Just A Friend.” That song became a crossover hit, becoming one of the first rap songs to crack the top 10 of the Billboard Hot 100.

On his 1991 album I Need A Haircut, Biz sampled Gilbert O’Sullivan’s 1972 hit “Alone Again (Naturally),” and O’Sullivan objected. (Biz loved the pop music of the ’70s, and he constantly quoted and referenced it in his own music.) O’Sullivan won the lawsuit, and Biz’s album was pulled from record-store shelves. That court case, along with a few others, changed rap practices regarding samples. When Biz finished the court case, he followed I Need A Haircut with 1993’s All Samples Cleared!, and he dressed up as a judge on the album cover.

In the late ’90s and early ’00s, Biz Markie eased into a role as a beloved rap elder. He made multiple guest appearances on Beastie Boys records, and he also guested on records for people like Will Smith, Chris Rock, Handsome Boy Modeling School, and Jay-Z. Biz appeared in the movie Men In Black II and on TV shows like Wild ‘N Out, Yo Gabba Gabba!, SpongeBob SquarePants, and Empire. He maintained a busy schedule as a DJ, and he started hosting a show on SiriusXM last year.

Biz was a deliriously silly and enjoyable presence, and the world was more fun with him in it. Check out some examples of his work below.