Director: Peter Spirer 

Peter Spirer was behind many of the notable hip-hop documentaries on this list, but none are as ambitious (or as successful) as Rhyme & Reason. It's not even that Spirer interviewed over 80 major artists for the film—it's the subject matter he includes that other documentaries fail to acknowledge.

Yes, Spirer gives us the requisite history tutorial, but he takes it to a new place, examining hip-hop's standing amongst other culturally significant types of music (like jazz and gospel), as well as their shared ties, namely a desire to be original and to give pain a voice. And while you're still thinking over the last connection he drew, he's on to another, splicing together potent scenes so that they play in an endless loop, like the break in the hands of a capable DJ.

But the film's greatest strength is in pulling on your nostalgia-inclined heart strings by following inner city kids, and then presenting questions about where hip-hop is heading by talking to the shortcomings embedded in the music. Such as, what does hearing women being called "bitches" and "hoes," as Lauryn Hill points out, do to a child's sense of respect for women? Big questions are posed by Rhyme & Reason and presented with such passion that we're inspired to find the answer to them ourselves.