This is a play on the expression “my cup runneth over” from the Hebrew Bible that signifies someone having even more than they desire. TI feels that he has been blessed, but concretizes the expression saying that his “cup” is overflowing with Pinot Grigio, a type of fine wine.

TI’s saying that a broke person telling him how divide the pies (money) is a blind person imparting the philosophy “eye for an eye,” because the blind person and poor person both have nothing to lose.

Diving the pie could both refer to how he chooses to spend his money or could refer to the act of dividing the economic pie, a term often referred to by economists when describing how to divvy up the pie (total GDP or money) between different economic sectors and classes.

This is a pun with the words “keys” and “kis”. Kis refers to kilos (kgs) of cocaine, and keys refers to piano keys like Stevie Wonder once skillfully played. So Wayne compares his skill with moving cocaine like Stevie on the piano.

This is double entredre:

1. A root canal is a dental surgery done when the tooth decays too much for a normal cavity or is infected. The surgeon kills the nerve and then usually has to put a crown, or dental cap, on the tooth.

2. A jeweled crown would signify that Joey, or Pro Era, are kings.

He asks why we’re even created if due to empirical data, we all die in the end anyways

Our lives are essentially meaningless when considered this way (cf. Schopenhauer’s Metaphysics of Love)

He wants them to at least “keep him on the shelf,” or be reminded or him every once in a while as keepsakes remind us of memories. He’ll come back to them one day, so he doesn’t want her to forget him.