As Lupe once said:

As a communicator, I’m gonna make sure that what I put out there is the truth. If I sell a million records, and it’s a lie on every single song, then I’ve sold a million lies.

Lupe’s lyrical content is more dense and complex than that of the music that typically sells. In a metaphorical sense, his music has the density of oil while others have the density of water.

“Blackbeard” probably refers to music pirates and those who leak his music (see Lupe’s OkayPlayer interview).

Lupe brought the “rock” into your ship – i.e.:

1. He sank your enterprise with a well-placed cannonball, like Blackbeard the pirate.

2. He caused you to run aground, like the huge rock on which the Exxon Valdez ran aground, spilling oil everywhere. This is meant to recall the image of oil-soaked fish in the previous line.

3. He attacked your team like the mythical Roc, a giant bird of Arabian legend, which attacked the fleet of Sinbad.

4. He brought the full force of Roc(-a-fella) to bear on your weak team by enlisting Jay-Z to Executive Produce his album and guest on this track.

Here, Lupe refrains from overtly calling out the drug game and simply using the metaphor of the “bad luck truck” as the equivalent of the drug game and its corrupting influence (“the boxes”) throughout Chicago, Lupe’s hometown.

This is also a reference to the unfortunate hand life dealt him from the beginning. Being from the westside of Chicago was like getting a box off the bad luck truck.

Lupe compares his music to old and worn Levi’s jeans (Lupe + Levis = “Lu-vis”) – he raps as a throwback to the lyricism of the days of old-school hip-hop

Also, notice the allusion to the violent gang Crips, whose primary color is blue. In keeping with this interpretation, the line could be read homonymically, as “O.G.’s covered in blue die”, which would serve to remind us of the tragic fate that befell Biggie and Pac (although Pac – via Suge Knight – was primarily affiliated with the Bloods..)

“Prince pants” refer to Prince’s now infamous backless chaps. Lupe is equating mainstream rap to the most ridiculous of styles and states that he has no interest venturing into that territory.

1st and 15th is Lupe Fiasco’s Record Label (which he co-founded)

1st & 15th is his sewing machine metaphorically because he makes and releases his music through this label, like a fashion designer complete their designs through a sewing machine.

Lupe starts out with an extended metaphor concerning the style and content with which he constructs his raps (the “jeans” he sews).

This is also a play on words for “so ingenious.”

Additionally, “so it seems” can be heard as “sew its seems,” meaning to sew the seams of a pair of pants.