Kendrick always shared how hip hop artist, Tupac Shakur, was his number one musical idol and inspiration for his musical style. To pay homage to the late artist, he began preparing to release an album entitled Tu Pimp a Caterpillar. As a recurring acronym user, Kendrick was strategic to ensure the album title would spell out the artist name Tu. P. A. C. This album was intended to be socially conscious and very politically charged. The topic of the plight of blacks in America society which he discussed in Section. 80 became an extended metaphor when he dropped his next album To Pimp a Butterfly. Regardless of the album name change, the message was just as powerful. He wanted to convey to his fans that despite how characters like Uncle Sam and Sally Mae are used to suppress blacks in society we would still be “Alright”. Alright was one of the his hit singles, it represented the resilience that has always existed in the black community since the Transatlantic slave trade. The album included other hits like”King Kunta” and “Hood Politics”. The album cover quit possible spoke louder than any of the lyrics ever could.The final song “Mortal Man” included a conversation between Kendrick and soundbites of the late Tupac Shakur. The song ended with a poem that perfectly dissected the meaning of the album and explained the metaphor of both the original title and the final title, as well as the transition of black men with the ongoing metaphor of them being considered caterpillars changing to butterflies.

“The caterpillar is a prisoner to the streets that conceived it
Its only job is to eat or consume everything around it, in order to protect itself from this mad city
While consuming its environment the caterpillar begins to notice ways to survive
One thing it noticed is how much the world shuns him, but praises the butterfly
The butterfly represents the talent, the thoughtfulness, and the beauty within the caterpillar
But having a harsh outlook on life the caterpillar sees the butterfly as weak and figures out a way to pimp it to his own benefits
Already surrounded by this mad city the caterpillar goes to work on the cocoon which institutionalizes him
He can no longer see past his own thoughts
He’s trapped
When trapped inside these walls certain ideas take roots, such as going home, and bringing back new concepts to this mad city
The result?
Wings begin to emerge, breaking the cycle of feeling stagnant
Finally free, the butterfly sheds light on situations that the caterpillar never considered, ending the internal struggle
Although the butterfly and caterpillar are completely different, they are one and the same.”

Rightfully so, he won five Grammy Awards, including Best Rap Album of the Year, for To Pimp a Butterfly. The cover featured the faces of himself and his close neighborhood friends posing with chains and money outside on the White House lawn standing on the body of a dead president. This cover was yet another form of resistance to the way blacks in American society are unjustly treated. Following the release of this album he dropped Untitled, Unmastered. With and olive green vinyl cover, he released eight songs without titles or production mastering which were demos that did not make the cut on his previous album. Although this album remained untitled and unmastered, it still reached number on the Billboard Top 200 and 178,000 units of album sales.