There is one argument against himself that Macklemore doesn't explicitly make in his just-released song, "White Privilege II," and it's important to get this argument out of the way because it's most likely the one to be used against this song in the long run. Throughout this song's four rap verses—and let's just call this a "song" for shorthand at this point; it's hard to tell if this thing succeeds as a piece of music—he outs himself as a self-doubting ally in the war against racism, sits confounded as he's congratulated by unconscious racists, places himself in culture-vulture crosshairs, and finally, reveals himself as a knowing recipient of white privilege. But, at no point does he broach the possibility of this all being part of an elaborate white savior strategy.
The idea is alluded to in the song's third verse, delivered from the perspective of an "old mom" (who's assumably white), but there's no direct acknowledgment that this entire thing, this "song," could be a complex play at making himself the protagonist of a story in which he should be the antagonist. Mere hours after the song's release, there were YouTube comments like "Macklemore wants to be black so bad" and and Twitter responses like "Macklemore will get a paycheck for making a song on White Privilege. That in and of itself is White Privilege." But clapbacks indicting the white-savior industrial complex are the bailiwick of professional activists who aren't necessarily the kind of rap fans who get first wind of a Macklemore song that's released in the dead of night. (Well, not always.)
So, yeah. Let's get it out of the way now: This song puts Macklemore in the conversation about Black lives mattering and—due to very same white privilege he's wrestling with in this song—he's going to get an inordinate amount of attention for speaking out. He's going to be vaulted to a level of authority in this country's high-profile discussions on race that's taken DeRay McKesson a lot more marching, organizing, and tweeting to achieve. By releasing this "song" at this particular junction of the national discussion and his own fame, Macklemore, by the grace of the white supremacy he calls out by name, moves from being an object of the conversation to a contributor to the discourse in a way that’s not always granted to Black and marginalized voices in this country.
This song puts Macklemore in the conversation about Black lives mattering and—due to very same white privilege he's wrestling with in this song—he's going to get an inordinate amount of attention for speaking out.
To get the scare quotes out of the way, this song is a mess, and there are just as many musical reasons to not listen to this song as there are political reasons to listen to it. We have four rap verses, internal monologues, a sung outro, chants, cinematic segues, keys both twinkling and ominous with no baseline, horn solos, and disembodied voices spread over nine minutes. It will (possibly, hopefully) make much more sense in context of his forthcoming album. How Macklemore (and by extension his partner, Ryan Lewis) addresses these topics in other songs and the sequencing and the sound of This Unruly Mess I've Made, have the chance at making this song work musically. As a pre-album single, it’s ballsy as fuck.
But this may also be the self-sabotage tendencies of an addict. It's hard to listen to this song and not hear the targeted destruction of a pop base. While Macklemore & Ryan Lewis have ascended to cultural heights, the rapper formerly known as Ben Haggerty has remained unsure about his place in hip-hop's hierarchy: "America feels safe with my music in their systems/ It suited me perfect—the role, I fulfilled it," he raps here, but it's an apology, not a boast. He asks: "Am I on the outside looking in?/ Or am I on the inside looking out?" And lest we roll our eyes at him, he gets all Eminem self-aware: "All the money you made/ Off the watered-down/ Pop bullshit version of the culture, pal/ Go buy a big-ass lawn/ Go with your big-ass house/ Get a big-ass fence/ Keep people out." All of these lines come from distinct perspectives: Macklemore the rapper, dealing with his own success; Ben Haggerty, a human being marching with protestors in Seattle; an anonymous hater.
"White Privilege II" is too messy to be ploy; too unruly to be calculated; too all over the place to be a chess move—unless the endgame is to piss off the "Same Thrift Shop Love Can’t Hold Us" demographic for a Black audience that seems unlikely to ever fully accept him.
The thoughts on the song are all first draft and journal-like; they’re like the raw materials of observation, but not the observations themselves. And that's what makes this song so riveting. It's the sound of an artist leaning on his craft in a moment of confusion; the soundtrack to a man going into the uncomfortable spaces within himself. It's not supposed to be perfectly constructed. Were "White Privilege II" too polished, it would not be half as powerful as it is. We have more than enough instances of Macklemore & Ryan Lewis pulling these kinds of ideas off—the original "White Privilege" (from 2005's The Language of My World) dealt with race insecurities in a more streamlined manner; "A Wake" (The Heist, 2012) dealt with his uncertainty when engaging social justice causes; most recently, "Downtown" proved that they still know how to latch on to a soaring pop hook. We're left to think that this song is exactly what Macklemore & Ryan Lewis want to say and how they want to say it. "What's your intention?" Macklemore asks himself in the second person. Then he repeats it, twice, almost breaking, and finding no answers. "What's the intention?"
"White Privilege II" is too messy to be ploy; too unruly to be calculated; too all over the place to be a chess move—unless the endgame is to piss off the "Same Thrift Shop Love Can’t Hold Us” demographic to appeal to a Black audience that seems unlikely to ever fully accept him. This song is too much to work as hit and not enough to work as a piece of agitprop. But, as a piece of art, it's like molotov cocktails in Capri Sun juice boxes, TNT stuffed inside packets of Crystal Light. It's a song that neither his fan base nor the mainstream will know what to make of. Is it good? Who knows. Is it fascinating? Definitely. It’s too controlled by its all caps "MESSAGE" to be work on conventional good/bad metrics. It’s barely a song, and at the same time it’s so much more than that.