Becoming a successful White rapper can be a tricky maneuver, and unfortunately, the race issue is bound to come up. This is not to say that skin color dictates skill level, but being in the rap minority could very well be an uncomfortable place for anyone. As such, White rapper prerequisites usually tend to include publicly speaking about the Black woman (or women) you had sex with, the Black people you grew up around, and speaking out against the "n-word," but also collaborating with artists who freely use the epithet.
It's quite a balancing act and because Macklemore is relatively just getting his feet wet in the White rapper pool, his internal struggle is very, very real.
New York Times writer, Jon Caramanica, speaks to his"white guilt" in a piece noting that the Grammy winner's reaction to beating K. Dot works to "reinforce the narrative of Macklemore as tortured intruder, keen to relish his success but stressed about all the shoulders he's had to step on along the way."
Other points that can be raised are that he's just being honest, and maybe looking for a little sympathy in the process. Of course, the irony here is that Hip-Hop was birthed out of non-acceptance, and has now become a club so exclusive that it can discriminate against others.
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