19. Black Sheep
Ah, Dres and the other guy...they seem to be the forgotten duo of the Native Tongues clique. To put it quite literally (which is super-unfortunate): they are the black sheep of that time and that place. But for a moment, they were the future: their first release, A Wolf in Sheep's Clothing, is considered a classic by many, one of the best debut rap albums ever. It went gold off of the strength of three Top 10 hit singles on rap radio ("Flavor of the Month," "The Choice is Yours," "Strobelite Honey"), as well as solid word-of-mouth.
Everything looked bright, until it didn't: their follow-up, Non-Fiction, only peaked in the triple-digits on the Billboard 200 chart, and then they were gone. Their legacy, too, has been tarnished: people now think of the staple "The Choice is Yours" because Kia Motors took the song, animated some dancing guinea pigs, and made a Super Bowl commercial out of it. This was all against Black Sheep's wishes, for what it's worth, which is not much.