Macklemore’s a white rapper, in dialog with his fans and himself on this track. He acknowledges that he may be “gentrifying” hip-hop as a white rapper in a black art form, similar to Eminem in “White America”. Macklemore doesn’t necessarily come to a resolution in this song—rap is who he is, but his privilege is a factor is his success. Also, future Thrift Shop collaborator Wanz said that this was the song that helped him gain respect for Mack:

He was the first rapper that I’d ever heard that would be so bold and so honest as to say a line, “We’ve taken their 40 acres, now I’m taking their 16 bars.” And that’s the line that hooked me, that got me to everything else, like “Other Side” and “Wings” and everything.

In 2007, Macklemore talked about this song, saying:

Me being white and being in a culture that started predominately with people of color, I feel like it’s my responsibility to address the issue, take it upon myself to do it in a fashion that examines it front and back.

When Macklemore got a mainstream following, he maintained this perspective which he discusses in an interview, years after this song was released.

On January 22nd 2016, a follow-up to this song, called “White Privilege II”, was released on YouTube and SoundCloud. The track will be a part of This Unruly Mess I’ve Made – Macklemore & Ryan Lewis' second studio album. The song analyzes a variety of issues centered around race that Macklemore feels are affecting the world still in 2016.