In the late 1990's Shyne was supposed to be the next in a solid line of Bad Boy success stories. Puff Daddy (Diddy) had deftly guided the careers of Craig Mack, The Notorious B.I.G., Ma$e and others to great heights, but this new young gun, Shyne, was to top them all. And he came out guns blazing, on tracks like "Bad Boyz" and "Bonnie and Shyne," with some critics, for better or worse, comparing his vocal stylings to Biggie.

But the train went off the tracks when on December 27, 1999, Shyne accompanied Puff and his then-girlfriend Jennifer Lopez to Club New York. Three people were injured in a shooting that Shyne was charged with; Diddy and J.Lo got off. Shyne went on to spend eight years in jail, convicted of attempted murder, assault, and reckless endangerment.

His musical ambitions obviously never came to fruition, with a few short-lived post-Bad Boy record deals. Today, Shyne resides overseas, his rapping style is best described as "hurting," and has only gotten attention for the many figurative shots he's taken at Diddy, 50 Cent, Rick Ross, and others. Much like Biggie, Shyne's career was ended far too early.