Shyne, born Jamal Barrow, is most recognized for his 1999 shootout with Bad Boy Puff Daddy and then girlfriend Jennifer Lopez than for his musical contributions to the Bad Boy Enterprise. The artist held a promising career until the evening that would change his life forever. At a night club in New York on December 27th, 1999 a ruckus occurred and led to Barrow pulling out a gun, firing shots at random (as the story is told, the shots were aimed at Diddy and his girl) before body guards secured everyone and the two men were charged with attempted murder in the second degree, assault and reckless endangerment. Diddy got out fine (only minor charges - including bribing a witness by giving J. Lo a diamond ring), as revealed in his rapper mogul status that has gone up since that evening, while the 21 year old Barrow was sentenced to ten years in jail.

Since that evening and the media frenzy that followed, Shyne released his debut album with BMG, the company that owned all those Bad Boys. The conglomerate, as reported by the Los Angeles Times, was considering releasing their ties with Bad Boys Records when Shyne's debut album appeared in 2000. The night club scandal and prison sentence did much for the budding rapper, who could only see the commercial success from behind bars. The album peaked at number five on Billboard's album charts but after the media died down, so did the attention to Shyne's music.

Considering Shyne couldn't even attempt parole eligibility until '09 the few fans he had left all but forgot about him. But in 2004 Def Jam signed the prisoner to a multi-million dollar recording contract and the rapper released his follow up album, Godfather Buried Alive, that year. Like before, the music was weak but got enough attention for more media reports to peak at number three on the Billboard charts.