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Biz Markie, a hip-hop staple known for his beatboxing prowess, turntable mastery and the 1989 classic Just a Friend, has died. He was 57.

Markie’s representative, Jenni Izumi, said the rapper-DJ died peacefully Friday evening with his wife by his side. The cause of death has not been released.

“We are grateful for the many calls and prayers of support that we have received during this difficult time,” Izumi said in a statement. “Biz created a legacy of artistry that will forever be celebrated by his industry peers and his beloved fans whose lives he was able to touch through music, spanning over 35 years. He leaves behind a wife, many family members and close friends who will miss his vibrant personality, constant jokes and frequent banter.”

Markie, whose birth name was Marcel Theo Hall, became known within the rap genre realm as the self-proclaimed “Clown Prince of Hip-Hop” for his lighthearted lyrics and humorous nature. He made music with the Beastie Boys, opened for Chris Rock’s comedy tour and was a sought-after DJ for countless star-studded events.

The New York-native’s music career began in 1985 as a beatboxer of the Juice Crew, a rap collective he helped Big Daddy Kane join. Three years later, he released his debut album Goin’ Off, which featured underground hits Vapors and Pickin’ Boogers.

‘This one hurts’

Markie broke into mainstream music with his platinum-selling song Just a Friend, the lead single on his sophomore album The Biz Never Sleeps. The friend-zone anthem cracked Rolling Stone’s top 100 pop songs and made VH1’s list of 100 greatest hip-hop songs of all time.

“This one hurts baad … RIP to my Aries bro,” Q-Tip of A Tribe Called Quest said on Twitter, where an outpouring of mourning for Markie was growing, “ahhh man @BizMarkie damn im gonna miss u so so many memories.”

Questlove said he learned from Markie early in his career.

“Biz built me man,” Questlove posted on Instagram along with a picture of him and Markie. “In my early early stages it was Biz who taught me the REAL places to cop records….Biz taught me what cities had good digging….Biz taught me where to collect 45s……Biz taught me where to collect 8TRACK TAPES!!”

Copyright infringement case changed music

After two successful albums, Markie was served with a copyright infringement lawsuit for a song on his third studio album I Need a Haircut in 1991. He and his label, Warner Bros Records, were sued by Irish singer Gilbert O’Sullivan who claimed that elements from his 1972 hit Alone Again (Naturally) were illegally sampled in Markie’s Alone Again.

The judge ruled to halt further distribution of the album, which was reissued without the illegal track. The judgment also changed the landscape of music sampling by dictating they were preapproved by the original owner.

WATCH | Just a Friend by Biz Markie:

Despite the setback, Markie released his fourth album All Samples Cleared! in 1993 that was an apparent reference to the court battle. He released his final album Weekend Warrior a decade later.

Markie kept his name relevant as he consistently booked more than 175 shows a year, according to the rapper’s website. He’s appeared on television shows including In Living Color and Empire along with black-ish and the 2002 movie Men in Black II, in which he played an alien parody of himself in the film starring Will Smith and Tommy Lee Jones.

Markie also taught the method of beatboxing in an episode of the children’s show Yo Gabba Gabba!

“We lost another Rap legend Mr. Biz Markie,” Parliament-Funkadelic bassist Bootsy Collins tweeted. “To a lot of us he was more than Just a Friend.”