Key Song: Shyne "Bad Boyz"

The best thing to ever happen to Shyne was Guerilla Black. Since Shyne really doesn't have much of a legacy to speak of—he released one forgettable album and one album while incarcerated—the emergence of Guerilla Black made us think twice about just saying someone sounded kinda like Big Poppa. But it wasn't Shyne who brought it to attention, it was other rappers like Big Pun who playfully mocked, "It's mine, I Shyne like money that sound like Biggie," and Kanye who claimed, "She be grabbing, calling me Biggie like Shyne home." But it was the Queen Bee, Lil Kim, that stung Po the hardest saying, ""Everybody wanna shine off of B.I.G./Get it, Shyne tryna sound like him when they rhyme." We're guessing Shyne longs for those days again, however, since prison has changed his voice so much he sounds like he's rapping with a mouth full of toxic sludge. —Insanul Ahmed