Before getting to “White Privilege II”, you have to understand that if any facet of Macklemore (Ben Haggerty)’s career were different, we wouldn’t be here.

If Macklemore was a white rapper from Detroit or Queens or (I guess) Sydney, Australia instead of a white rapper from Seattle, we wouldn’t be here. If he had rap industry cosign from someone like Dr. Dre or T.I. and didn’t operate in a DIY vacuum, we wouldn’t be here. If his party banger was the single that resonated with White America and not the two that by intent or by accident threw hip-hop writ large under the bus and inadvertently positioned Mack as rap’s Great White Hope, we wouldn’t be here. If dude was just a better artist (I’ll come back to this one), we probably wouldn’t be here.

But, because life is a series of events we don’t control, here we are in world where Macklemore and Ryan Lewis released “White Privilege II” the only way a song like this could be: by lobbing it on iTunes at midnight last Friday like a molotov cocktail and clearing the area as fast as possible. “White Privilege II” is a nearly 9 minute mess consisting of 4 wordy rap verses, 2 spoken-word collages, a choir-esque interlude, and a sung outro, all laced with roiling self-loathing, guilt, and cloying purpose. Its tone pivots from slam poetry to After School Special to screaming in the hotel room, each leaning all the way in on Macklemore’s patent earnetness. His scattered approach extends to Ryan Lewis’ production, where solemn, leaden piano gives way and snaps back from a jazzy freakout and vaudeville vamp while occasionally tossing that chanting choir in. “White Privilege II” is, in other words, a lot.

Before anything else, let me say this: “White Privilege II” is worth listening to at least once. It is, at the very least, a genuinely felt piece of art from someone who wants their heart to be in the right place, and is willing to try very, very, very, very hard to say something meaningful, even if they aren’t sure what. It is much better than saying nothing. I’m not going to over-praise Macklemore by calling the song “brave”, but putting it out in pre-release is a gutsier move than it just popping up most of the way through This Unruly Mess I’ve Made.

What I’m not sure of yet is if “White Privilege II” works or not. Part of that is going to be if the song hits that resonance that “Same Love” or “Thrift Shop” did with time, but largely it’s because I’m not sure if this sprawling, restless thing is a noble experiment or just a failed one.

It absolutely doesn’t help that the song’s first leg is also its weakest. This is the slam poetry one, where Macklemore raps about going to a Black Lives Matter protest and feeling awkward. It’s slight because Macklemore wrings his hands over the perceived oddness of being a white dude at BLM event without exploring where his unease comes from, or wonder what it’d be like for black protesters (part of this might come down to perspective. It’s really hard for my black self to resist going “Poor Ben, you felt uncomfortable at a protest.” He went, and that’s great, but dude). There’s some righteous anger there, but Macklemore doesn’t gain much by swinging hard at police brutality.

He finds much more to sink his teeth into during the song’s second and third verses, the former of which is the “screaming in the hotel room” section. Like Kendrick Lamar on “u”, Macklemore is absolutely ripping himself to shreds here as an exploitative faker over freaked out horns while teetering on the edge of self-destruction. It doesn’t quite match “u” in execution (those first few shouts of “LOVING YOU IS COMPLICATED” will never not destroy my soul temporarily), but it’s an arresting performance by a guy who dreads what he’s created.

From there, we get to the most inspired and the only part of “White Privilege II” that’s downright compelling: the “old mom” verse. Macklemore raps from the point of view of a middle-aged white mom praising him for being “The only hip-hop that I let my kids listen to…” and the verse is 1. performed in such a pitch perfect way that I have to think Macklemore has met people like this who terrify him, and 2. a crueler rebuke of Macklemore than what anyone else will ever come up with. It plays to Mack’s strengths as a storyteller while handily connecting white audiences’ reaction to “Thrift Shop” and “Same Love” to their ire for Black Lives Matter protests.

Unfortunately, this is only half of “White Privilege II”, which turns into a chore for its last 4 and a half minutes. You get two sound collages: one of which is a tedious read-through of “I’m not racist” racist shit you see on Facebook, the other is activists talking about Black Lives Matter as a liberation movement for all, and what role white people can take in helping society. Macklemore delivers his #TruthBombs white privilege verse with the same seriousness he used in “Same Love” (ctrl+f “Verse 4” here; it almost sounds better read) that, while it’s great and necessary, feels tiring, and by the time Jamila Woods descends from “Sunday Candy” heaven to sing the outro after seven and a half goddamn minutes, you’re left reeling.

I might be wrong. As a black man, I am fully aware that “White Privilege II” is not written for me. I still maintain it’s a song worth listening to and engaging with, but I also think for how hard it tries, “White Privilege II” is a well-intentioned failure.

Here’s what I keep coming back to: who is this song for? Because I don’t think it knows. The first third or so of it scans almost like an apology to black people or hip-hop fans while the rest is pretty plainly directed at Macklemore’s white soccer mom club. But addressing these audiences this way is baffling: the black community and hip-hop heads have never especially fucked with Macklemore, and the white privilege/supremacy verse itself (y’know, the song’s entire point) is in the last one here. It’s nearly counter intuitive.

Earlier, I said “White Privilege II” wouldn’t exist if Macklemore was a better artist. There are a couple of levels to that. If he was a better rapper or sharper lyricist, he probably would have beat back the appropriation criticisms by now (see: Mathers, Marshall). Likewise, because of his perceived lightweight status, just approaching “White Privilege II” requires some critics/listeners to drop the “Oh, fuck that guy” reaction that comes with news relating to Macklemore. And a lot of the song’s messiness comes from Macklemore being self-aware enough to acknowledge his white privilege, but not self-aware enough to use that privilege in a smart way (see: The infamous Screenshot).

That critical lack of self-awareness is what kneecaps “White Privilege II” chances at reaching mass culture. The song’s most intended audience–let’s say the old mom in the third verse–was introduced to and knows Macklemore from “Thrift Shop” and “Same Love”: songs that sure, have a message, but are pop songs first. They followed a verse-chorus-verse structure with repeated hooks and manageable run times, and, because they fit comfortably next to P!nk and Bruno Mars singles on top 40 radio, were able to win over the masses over time by invading the country’s shopping centers, waiting rooms, and Steak and Shakes. Meanwhile, there are like, seven different reasons why “White Privilege II” won’t get any radio play, and that’s before you get to the content. Risk-averse pop radio isn’t going to play it because it’s a nine minute track without a hook whose structure borders nonexistent, and rap radio isn’t going to play it because it doesn’t hit hard enough  (plus “it’s Macklemore“). On an academic level, it seems apt to fail, as well: it’s been discussed by people of color far more than white people.

So, in the end, “White Privilege II” is like its creator: stuck in the middle between exasperatingly too much and woefully too little, losing with the wrong people, winning with the wrong ones, besieged on every side, but trying so very hard. Macklemore seems almost trapped by his fame and success in a way he finds deeply unsettling, and “White Privilege II”, his shot at getting out, looks like it was thrown away. Maybe it’ll make more sense within the album’s context, or maybe “White Privilege III” will arrive with a clearer sense of purpose. But for now, we’re left with his song, Macklemore’s unruly mess. We heard he was conflicted.