"White Privilege" is a good song, and you should hear it. I'm referring to the 2005 song here, for a hot second, before we dig into the sequel.

The original "White Privilege" is a cut from Macklemore's debut album, The Language of My World, which many long-haul Macklemore fans regard as the Seattle rapper's unsung classic. While the album predates his association with his current producer, Ryan Lewis, The Language of My World has all the kumbaya handclaps and sincerely progressive theorizing that you'd expect to hear at any given phase of Macklemore's career.

"White Privilege" is Macklemore's mission statement, crafted as a denunciation of his own privilege and stressful declaration of good faith. The song is not the work so much as it's the promise to do the work. To this day, Macklemore is obsessed with this promise. He'll never fulfill it completely, and so he will never live it down.

So now we have "White Privilege II," the new album single that Macklemore & Ryan Lewis released Thursday night. "White Privilege II" is not a good song. "White Privilege II" is a goofy, confused composition from an anxious man who, with more than a decade's head start, still hasn't settled comfortably into conversation with hip-hop, black audiences, or white power. Rather unfortunately, "White Privilege II" opens with whiteface mimicry of former GRAMMY rival Kendrick Lamar's latest album, To Pimp a Butterfly, with a field chant and a tenor sax blasting listeners in the back of their skulls; and it closes with twinkling, man-on-street chatter, sounding rather like an episode of This American Life. It's literally the whitest song ever recorded.

What should a white ally be? How should they sound? When should they speak, and to whom? Godspeed Ben Haggerty in his tireless inquiry, which is thankless. To his credit, Macklemore does at least seem to appreciate that he's marginalizing his credibility within hip-hop, and among supposedly advanced liberals, by being so sincerely offbeat, as if he were a child. For Pitchfork, the rap critic kris ex—who once profiled Macklemore for Complexcharacterized the political thought of "White Privilege II" as "first draft and journal-like," pardoning the mess of dramatic musicianship as "the sound of an artist leaning on his craft in a moment of confusion​."

For Macklemore, that moment has somehow spanned 11 years, not entirely without advancement. On "White Privilege," Macklemore was just rambling to himself. On "White Privilege II," which is twice as long and at least twice as ambitious as the original, he is marching and listening to activists at a #BlackLivesMatter protest. He's engaged. He's irritating, still, but here he's come to appreciate that there's a whole wide world of independently realized black lives beyond his own disastrous introspection. He's learning. In his naïveté, Macklemore isn't exceptionally white. Macklemore is white like you.

In lieu of absolution or action, Macklemore aspires to wokeness. "I'm sexist, I'm prejudiced—I put that in my music," Macklemore once rapped on a song called "Contradiction," where he's once again indistinguishable from the white guilt industrial complex that's otherwise disavowed Macklemore with the quickness. As much as I want to discount all his prostrate apologies as hyperactive cognitive dissonance—as many other listeners have, ever since Mack beat Kendrick for that Best Rap Album GRAMMY in 2014—I think it takes guts to make a nine-minute song about what you don't know and can never bear. I think "White Privilege II" is a startling exercise of humility. I think it sucks, but whatever.

Upon the release of "White Privilege II," Lindsay Zoladz, a pop critic at New York magazine, tweeted, "if it took you a Macklemore song to realize any of the points he is making in that Macklemore song, i don't even know what to say to you."​ I suppose this sort of intellectualized distance between middlebrow and lowbrow, between the middle and working classes, between white and "all-American," is what Macklemore is getting at when he asks, "Am I in the outside looking in? Or am I in the inside looking out?​"

In 2016, hundreds of thousands of registered voters are eager to elect Donald Trump, a crypto-fascist, as president of the United States, and somehow no one who says for a living knows what to say. Even white power doesn't know how to talk white power off the ledge. Macklemore, short of just quitting hip-hop, pronounces his ignorance in such dumb but exceedingly respectful, comically provocative ways that naive white listeners might relate to and really heed.

White guilt is effortless and cheap; "White Privilege II" is a chore. That's saying something. The song is bold if only insomuch as the white man has invited a black woman, the singer Jamila Woods, to have the last word about hip-hop. "What we made, we made to set us free​," she sings.