Jamal “Shyne” Barrow became a household name on December 27, 1999 — the same day his new Hip-Hop and reggae single “Bad Boyz” was released on the airwaves. The Belizean-born, East Flatbush-raised emcee collaborated with reggae and dancehall phenomenon Barrington Levy for the first single off his self-titled debut album Shyne on Bad Boy Records.

On that same New York winter night, Shyne stepped out to a New York City nightclub with label exec “Puff Daddy” and their entourage. A notorious shooting inside the venue made headlines with the 21-year-old rapper facing charges of attempted murder, assault, and reckless endangerment.

While Shyne awaited trial, Bad Boy promoted the videos for “Bad Boyz” and “Bonnie and Shyne” — both featuring vocals by Barrington Levy — and the Foster Sylvers-sampled “That’s Gangsta.”

The Shyne album — with no featured rap vocals; only his own — topped the charts and eventually saw platinum status. What would become of an enterprising young man with a promising music career, signed to one of the hottest Black-owned record labels?

“I TOOK THE FALL FOR MY FRIENDS. BUT THAT’S THE WAY LIFE IS.”
— SHYNE

By the time his first album came out, Shyne already began serving a 10-year prison sentence at Clinton Correctional Facility in upstate New York.

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