Craig Mack, the rapper who had a couple of absolutely iconic moments on Puff Daddy’s Bad Boy Records in the early ’90s, has died. The New York Daily News reports that Mack died of heart failure at a hospital near his South Carolina home yesterday. He was 46.

Mack, who grew up in Queens, started rapping in 1988, under the name MC EZ. But he came to fame in 1993, when he rapped a guest verse on a remix of Mary J. Blige’s “You Don’t Have To Worry,” which appeared on a the soundtrack of the movie Who’s The Man? In 1994, Mack released his massive single “Flava In Ya Ear,” which made the Billboard top 10 and earned a Grammy nomination. The even-more-iconic “Flava In Ya Ear” remix, which came shortly afterward, helped launch the careers of the Notorious B.I.G. and Busta Rhymes, and its stark black-and-white video, which Hype Williams directed, is still copied today. It’s one of the all-time great posse-cut remixes — maybe the greatest ever.

Mack released Project: Funk Da World, his debut album, a week after his Bad Boy labelmate Biggie released Ready To Die. While Project: Funk Da World went gold, Mack was quickly overshadowed by both his more-famous labelmate and by Puff Daddy, his label boss. Mack soon parted ways with Bad Boy; his sophomore LP, 1997’s Operation: Get Down, came out on an indie label. Mack resurfaced on Bad Boy long enough to appear on the remix to G-Dep’s 2001 single “Special Delivery,” but he’s been largely out of the spotlight in recent years. He apparently converted to Christianity and joined up with the Overcomer Ministry, which, at least according to some people, is a cult.

Mack’s career might not have gone the way he must’ve hoped, but very few rappers will ever have a song as massive as “Flava In Ya Ear,” which was an absolute monster in its day. The world would look very different today if it had never come out. And Mack’s rap delivery — scraggly, erratic, given to swallowing entire syllables and switching up cadence without warning — had few parallels. He was a glorious weird. Watch some videos below.