On this day, Dec. 27, in hip-hop history...

RJ Capak, Getty Images

1999: A few days after Christmas, Belize-born and Brooklyn-raised rapper Shyne and his then-girlfriend Monay Hawkins went to partake in post-holiday celebrations with Shyne's record label boss Sean "Puff Daddy" Combs and his girlfriend at the time, Jennifer Lopez. The two couples hit up a club in Manhattan called Club New York.

The young rapper, born Jamal Barrow, had a debut album on the way and everything was looking up for Bad Boy Entertainment's next rising star. All that changed when a fight broke out inside the club and Shyne, then 21 years old, pulled out a gun and started firing into the crowd. The incident left three people injured. During the melee, witnesses say they saw Shyne holding a smoking gun, which ultimately sealed his fate.

Shyne would go on to face a high-profile legal battle that eventually got him dropped from Bad Boy Entertainment. He was convicted of criminal possession of a weapon, assault and reckless endangerment, but found not guilty of attempted murder, and sentenced to 10 years in prison. Shyne went on to serve nearly nine years of his bid and when he was released in 2009, he was deported back to his native Belize.

Though he's been living in Belize for years, Barrow is not forgotten by the hip-hop community. In 2016, he even made an appearance at the Bad Boy Reunion shows in Brooklyn, N.Y. via satellite to perform his biggest hit, "Bad Boyz."

19 Pics That Show What Shyne's Life Is Like in Belize