24. Sean Price "Figure Four" (2009)

These are words from a thousandaire. Sean Price might be the brokest rapper you know, but he's also the one rapper who truly sounds comfortable in his own skin even  if he's often vexed about his finances. He can easily flip between describing drug-infested blocks to shouting out an Internet blog ("What up Eskay!") without shedding an ounce of street cred.

He takes light shots at bigger stars like Wale and Jay-Z, yet it's more playful than malicious. Price gets to have it both ways. These lyrics aren't exceptional for their wordplay but because they so accurately paint a picture of a wily veteran who's been beat, but isn't beaten, slowed down but still going, and down but not out. —Insanul Ahmed

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