It'd be fair to say that, when it comes to race, Macklemore has been pretty clumsy throughout much of his career. There was the time he sent Kendrick Lamar a text message apologizing for winning Grammys—and then Instagrammed the text to let the world know that he sent it—and there's been serious, smart critique of the race and class issues in songs like "Thrift Shop." But Macklemore is hardly alone in that—in America, in 2016, "clumsy" is one of the nicer words you could use to describe how white people act when talking about race.
The new song that Macklemore and producer Ryan Lewis released last Thursday night, "White Privilege II," is definitely still clumsy: It's nearly nine minutes long, features a series of distinct musical movements, includes four verses, three spoken interludes, a chanting chorus, and a soaring outro vocal from singer Jamila Woods.
In some ways, that's a missed opportunity. Say what you will about Macklemore and Ryan Lewis, but if the duo has one defined talent, it's creating catchy, earworm tracks that can take a single idea and transform it into something that gets stuck in your head for days. Even if you hate "Thrift Shop," you've probably found yourself humming it against your will from time to time. The fact that "White Privilege II" is a ponderous, extended, sprawling piece that announces its importance with a capital "I" that sounds more like an outtake from Hamilton than a club banger is kind of too bad—making people dance to an examination of white privilege, racism in America, and the importance of the Black Lives Matter movement would be an impressive feat for Macklemore and Lewis (or anyone).
That's something that Hollis Wong-Wear, a frequent Macklemore and Lewis collaborator who worked on "White Privilege II" as a songwriter for over a year, recognizes. "You could argue that the most effective way to do it would be to use the pop structure to create something that's palatable," she admits, "But I think the idea of having it be open-ended and letting there be movements that are articulated allowed for a more expansive approach, and is such a product of the input from the various collaborators."
The collaborators that Wong-Wear refers to are an array of women and men who've been involved in the Black Lives Matter movement and general anti-racist activism in Seattle and elsewhere for some time. Wong-Wear has been working with Macklemore and Ryan Lewis for years; many of the other collaborators have spent the time since their rise to fame being decidedly more critical of the duo in regards to race and the choices they've made.
"I was honestly wary at first because of what it sounds like: 'Macklemore doing a song about Black Lives Matter...," writes Jamila Woods, who's credited as the featured artist on the track and who lends her soaring vocals to the song's final 90-second outro, on a website launched by Macklemore and Lewis to explore the process. "When you hear that for the first time, it’s only natural to give it a side eye." She participated, she says, because she wanted the opportunity to address Macklemore's white audience. "I always approach writing from a place of love, not a passive love but an active love," she writes. "An I’m-gonna-tell-you-when-you’re-messing-up-because-I-love-you kinda love. That’s how James Baldwin talks about his relationship to America."
She's not the only person who was involved in the process of creating "White Privilege II" to express that sort of concern. Activist and poet Nikkita Oliver answers the question that people in activist communities are likely to ask her: "Why work on a track about white supremacy and Black Lives Matter with Macklemore?"
"As a black member of hip-hop culture, I had (and in some ways still have) my reservations," she writes, explaining that as she came to know Macklemore as a person, she believed in his intentions with the song—which presented an opportunity. "As much as it pains my humanity to admit, most white people will not listen to me when I speak about my experience and white supremacy. Macklemore has a platform in the ear buds of white youth all over the United States."
That makes a lot of sense—but it's also fair to question what they'll be hearing when they listen to "White Privilege II." The song's first verse is from Macklemore's point of view as he questions whether he's allowed to participate in a Black Lives Matter march, and what chants are appropriate for him to participate in. It's curious to hear someone work out their racial discomfort in public, on a high-profile song, from one of the world's most famous rappers—but the second verse, where he raps in the voice of the (usually black) critics who've called him out for his appropriation of hip hop, raises even more questions. In the third verse, the perspective flips again—this time from a white suburban mom who lets her kids listen to Macklemore, but not to black artists, and who feels comfortable expressing her subtle racism to him in public.
All of that is a bit weird. Rapping in the voice of your critics is, er, an unusual way to respond to allegations of appropriation, and it's hard to say for sure that anyone is enlightened to learn that Macklemore is uncomfortable with the fact that he has racist fans. But when the song gets to its fourth verse—four and a half minutes in—you can hear what comes from having a consortium of highly engaged voices go back and forth with an artist about heavy issues like race, white supremacy, institutional racism, and white privilege. Insights like "My success is the product of the same system that let off Darren Wilson" can't be easy to express, and questions like "We take all we want from black culture, but will we show up for black lives?" are questions that not just artists like Macklemore, but also his fans—and white rap fans who think Macklemore is corny, but who've been playing To Pimp A Butterfly all year—need to be asking, too. The framing of these things is clever, and important here—being told that you've received privileges you don't recognize tends to make white people who haven't thought about those things much defensive, but Macklemore telling those people that he's received those privileges can cut through some of that.
"One of the strengths of the song is that he never asserts intellectual superiority," Wong-Wear says. "He implicates himself as much or more than anybody who's listening who's white, and throughout the process, it was always about ensuring that it was never coming from a place of, 'Now that I've figured it out, here's what you should do!', but more of a place of compelling the audience to ask themselves questions similar to the ones that he asks himself on the song."
It might be nice to get to that point sooner than happens on "White Privilege II." It might be nice if that came through in a track that had the potential to be banging from car stereos and on earbuds all year long—the odds seem good that, when the new Macklemore & Ryan Lewis album is released, "White Privilege II" gets skipped past in favor of the fun tracks. It's definitely not a perfect song—it sounds like all of the things that Macklemore spent the past year thinking about got stuffed into a single overlong track that desperately needed an editor—but words like "messy" and "disjointed" are usually going to be appropriate in most conversations about race in America in 2016. If Macklemore brings that conversation to white teenage fans who've had the privilege of avoiding it, then "White Privilege II" is going to be important anyway.