The satiric usage of three K’s misspelling America as Amerikkka alludes to the Klu Klux Klan, drawing to a perceived notion of underlying or inherent racism in American society.

Gods would also tend to replace the letter c with k due to the fact that they believed the white man to have twisted their language and written all letters with the “K” sound as “C” instead during their first encounters. This is why many five-percenters or Nation of Islam members may spell “Africa” as “Afrika” instead.

The Ku Klux Klan did the very same thing although for an obviously different reason. This is probably just a simple coincidence, but an interesting one at that.

Reaganomics refers to the systematic redistribution of wealth upwards (whether intentional or not), based on the assumption that certain tax breaks and monetary policies will cause the wealth of the top 1% to “trickle down” to the lower classes at some point. Hailed by Republicans, and criticized by others, Reaganomics remain a controversial subject in economic circles.

Continuing from the previous three lines, he wishes he didn’t care about this generations problems because he has plenty of problems himself. He knows he shouldn’t even speak on it because it is not his own personal issue, but as we see in the next verse, he sometimes does speak on these types of things in spite of that because he realizes his music reaches a large audience and could potentially help someone.

He is commenting on how people view rap about guns, drugs, and sex as worse than conscious rap. However, all the supposed negative aspects of rap music are byproducts of society, not of rap.

People complain about talk of guns, yet America’s history is deeply connected to the right to keep (legally) firearms.

The subject of drugs is considered immoral yet it is a well documented fact that president Ronald Reagan and his administration facilitated the smuggling of drugs into our country and specifically into the ghettos and urban areas.

Finally, Mack concludes that the subject of sex is not intentionally included on songs to sell records, but simply a large part of the human psyche and therefore an unavoidable subject in a society based on free speech.

Also, he often is praised (which he feels wrongfully) by the media for apparently not including these topics in his music. Macklemore dismisses them because he knows he’s not the first to speak about these issues and he feels as if those people are downplaying other rappers before him for speaking out as well.

Mack is referring to interviews in which the interviewer refers to his lyric as “true poetry”, placing it ahead of other forms of Hip Hop as far as value. He finds this offensive because he doesn’t see himself as better than other rappers.

This also establishes what becomes the theme of this whole verse: the tension he feels as a white rapper in a mostly black genre, the tension that he references later between feeling white privilege and white guilt. Here he is suggesting that a lot of those interviewers might be subtly discriminating, subtly critiquing the rappers who aren’t as “well spoken” as this white rapper, and he’s saying it pisses him off when they ask him questions that put him in a position to accept the praise of being “well spoken.”

They are willing to give him $100,000 dollars that he’ll have to pay back, basically making it a loan. The label offers him a 360 deal and spins it in a way that makes it seem like they care about all of his goals in music and business, not just his debut CD.

360 deals have become very common as record labels continue to lose money from piracy and digital distribution. These deals inject the label into more if not all revenue streams of an artist. Labels historically didn’t see a dime of merch sales and little from touring as well.

Macklemore uses a clever play-on-words – “a loan” is interpreted (misheard) as “alone” by Iovine, implying that Iovine isn’t actually attending to Macklemore, maintaining the casual lack of concern he exhibited when he forget Macklemore’s name earlier.

As Mack starts to doubt his plan, he comes up with the idea to take one of the A&R reps hostage if he gets caught. He is probably referring to either Steve Berman (head A&R, the Steve Berman of Eminem infamy) or John Ehmann (urban A&R)

A&R stands for Artists and Repertoire, a liaison between artists and the record label or publishing company; every activity involving artists to the point of album release is generally considered under the purview of, and responsibility of, A&R.