In Shakespeare’s time, a jester (modern day joker) was someone who was hired to entertain someone of power by making a fool of themselves. They were paupers. Here, Akala likens this to not wanting his music laughed at, and would rather be seen as a poet, or at least a lyrical artist, rather than the pauper/jester.

Alternatively, given that a large debate exists as to the identity of William Shakespeare, Akala could be referring to the playwright himself. Some speculate that he was a pauper, who used a posh pseudonym in order that his plays be taken seriously, others speculate the exact opposite: that he was a very rich man who wrote for the lower classes. We may never know exactly who William Shakespeare was, but his true genius lies is in the way that his plays are so textured that they are accessible to absolutely anyone, poets, paupers, rich or poor.

Dilated peoples have been underground rather than mainstream. Here they use the metaphor of a hot flame getting hotter much like 2pac before he was mainstream.

Using the play on words of dosing acid (LSD) which gives you a high. Plan B here wants to get his high from sexual activities with Charmaine.

Omar is a character on HBO’s The Wire. Omar died out of nothing on the show, when he still had a lot to do much like what is being explained in this verse.

Ill is known for winning rap battles and if he doesn’t he doesn’t care because he knows he will still be remembered

Illmaculate has earned his spot because he is a two-time World Rap Champion

Pleading the fifth is an amendment in which witnesses can refuse to answer a question in court which may incriminate them. He is saying that he would rather plead the fifth than lie.