Before we get to my thoughts on the tweet that nearly blew up the rap internet:

I’ve been enjoying this series of documentary shorts that followed Macklemore and Ryan Lewis around the globe last year during their Fall World Tour. The clips have been insightful, entertaining and, at times, even uplifting. Episode five (above) went up yesterday and concludes the series. It’s worth spending the 22 minutes to watch.

And now, because I can’t leave well enough alone…

Regardless of how you feel about Macklemore’s success — recently manifested in the four “gold sippy cups” he collected in Los Angeles this past Sunday — the big takeaway from the Kendrick Lamar tweet is that the man’s life has become one massive no-win situation. Being white, and a rapper, and blah blah blah, leaves him open to unique criticisms that otherwise aren’t applied to many of his pop star peers.

Having said that, I think most of the critiques are warranted — the smart ones, anyway — and, ultimately, valuable in the grand scheme of things. The fallout from Macklemore’s success, as it pertains to the non-white and non-heterosexual communities especially, is a messy business. There are bigger societal concerns at play here that have nothing to do with Macklemore the person, and everything to do with our culture’s frustrations and fears. It seems Ben Haggerty has become America’s favorite proxy for its grievances which is spurring mass conversation.

I don’t know Macklemore personally. I shook his hand and spent about ten minutes in a room with him a few years ago, but we never shared a conversation. But by all second hand accounts from people who do know him, he sounds like a good guy. Even when he participates in stunts that draw a raised eyebrow — editing down “Wings” in order to fit the NBA’s All Star Game marketing agenda; playing a role in the dubious mass wedding at the Grammys; the curious tweet to Kendrick Lamar — I never really doubt his honesty. In these scenarios it seems like he’s either being earnest to a fault, or led to participate by the sort of denial that could only be catalyzed by a sudden and disorienting amount of fame. The machine that he’s chosen to dance with is unforgiving and dispassionate and cares nothing for an artist’s personal principles.

With regards to the Kendrick tweet specifically, what was probably meant as a generous and heartfelt admission came off as an awkward and ill-advised form of damage control: a way of diffusing some of the anger “real” hip hop heads may have felt about Kendrick not winning the award. But if we’re being honest here, those so-called “real” heads already know what time it is. They don’t need Macklemore to tell them Good Kid M.A.A.D. City should have won, and they don’t need him to explain the function of these awards which are handed out annually in what essentially constitutes a magical pop culture vacuum. To make his message to Kendrick public was to insult the intelligence of the hip hop literati.

So consider the tweet a simple misstep in a career that will likely continue to be filled with them. Macklemore is a white rapper who was just certified as the best in his field by the biggest music awards show in the world. He will stumble again because the field he’s playing on is the slipperiest slope of all.

[Update, 1.30.14, 7:15am PST: Kendrick’s even-handed, democratic and existential response.]