"You got robbed," begins the most guilt-ridden apology of the 21st century. "I wanted you to win. You should have. It's weird and it sucks that I robbed you." The screencap seen 'round the world explains the duality of Ben Haggerty, aka Macklemore, whose unexpected mainstream appeal has enabled him and his music partner, Ryan Lewis, to rise to the top of the industry. At the 2014 Grammys, the duo’s The Heist had defeated Kendrick Lamar’s good kid, m.A.A.d city for the Best Rap Album Grammy, an upset that weighed on Macklemore’s conscience. He reached out to Lamar, screencapping the mea culpa for Instagram so everyone could see how just how hard he’d fallen on his sword.

Macklemore understood that the only people who thought The Heist was better or more important than good kid were Grammy voters and misguided white teenagers. But he also needed deeply for the world to know he understood. This same tension between humility and ego fueled his crossover smash hit "Same Love," which advocated for the very non-controversial idea that "being gay is okay" and made them unlikely spokesmen for easily digestible social justice. It also prompted criticisms that they weren’t ready to preach from the mount, and after a few years spent internalizing those criticisms, they’ve returned with This Unruly Mess I’ve Made, a blend of juvenile joke raps, inquisitive woke raps, and diaristic contemplations of Macklemore’s life that attempts to prove they belong—that they’re not just white saviors trying to project their face onto the culture.

"Music was intended to be that one thing that we could rely on to disrupt the norm," Macklemore said in a video announcing the album. "Start conversations and change the way that we think and we feel." When he released "White Privilege II," a sprawling monologue in which wonders if he’s an interloper and lectures about the literal definition of white supremacy, he didn’t just drop the mic and try to let the song speak for itself. Instead, he gave interviews about the song with non-white publications, and launched a website in which he and his collaborators—including Chicago singer Jamila Woods (who sung the hook on Donnie Trumpet & the Social Experiment’s "Sunday Candy"), community organizer Dustin Washington, activist Nikkita Oliver, and more—detailed its conception. There was a lot of effort to convince you he was taking the issue of white privilege very, very seriously. Call him the rap game Matt McGorry—the rare white pop star making political music with explicitly middlebrow outreach.

And make no mistake, Macklemore is taking a lot of issues very seriously. "Same Love" wasn’t complicated, but it put a human face on gay marriage that was able to connect with millions of Americans. Here, the clattering funk of "Kevin" reaches for a similar understanding about the prescription drug crisis, as the accessibility of opioids like Oxycontin has devastated low-income (and white) communities across the country. Macklemore is a former addict, and his invective about the parasitic sway of drug abuse ("We play Russian Roulette/ And try to find a life where we could be content/ ‘Cause for us, we're just trying to minimize the fear of being alive") carries the moral authority of lived experience. (In interviews, he’s said he also lapsed back into his addiction within the past few years, giving his words a different urgency.)

But Leon Bridges’ hook is too moralizing, and it has the maudlin feel of a song written to solve a problem. Macklemore has more appeal as the everyman—a normal guy who who just stumbled into all this pageantry. On the opener "Light Tunnels," he narrates a trip to an awards show: He feels desperately out of place in his town car and his tux, the industry’s eyes on him without his friends for support. ("I wish I had the homies with me here but nope/ Most of the artists I know don’t get invited to this show.") He waxes about how "they" want gossip, drama, for Kanye's rant "to go on longer." As he accepts an award (which may be the Grammy he robbed Kendrick of), he ponders how he’ll explain "this unruly mess I’ve made"—a slightly disingenuous "aw shucks" characterization of his career that nevertheless communicates some truth about the weight of his expectations.

"Buckshot," meanwhile, reflects on his days as a rebellious graffiti artist, featuring KRS-One and DJ Premier, and "St. Ides" is a tender travelogue of his days as a teenage alcoholic. On "Growing Up," Macklemore dictates a comprehensive list of cool-dad lessons for his newborn child ("Listen to your teachers, but cheat in calculus"; "Take your girl to the prom, but don’t get too drunk hanging out the limo.") His knowledge is slightly undermined when he recommends reading Langston Hughes’ A Raisin in the Sun (Langston Hughes did not write A Raisin in the Sun), but hey, nobody’s perfect.

He developed the big-tent struggle gospel sound of The Heist with Ryan Lewis after a decade spent as an underground rapper, and the formula hasn’t changed much here: There are still lots of choirs, dramatic string cues, and dewy pianos set to tug heart strings. Even a goofy song like "Dance Off" gets a swelling horror-movie organ intro before a big dancehall rhythm kicks in. It’s atypical backing music for a rap album, but Macklemore is kind of an atypical rapper. His cadence tends to fall between "impassioned slam poet" and "guy talking in your ear," and when he’s doing the latter, the lights dim on the production. "The Train" is set solely to piano and the sound of a train whizzing over the tracks, as he softly raps about how his growing responsibilities have pulled him away from his family. "St. Ides" is almost completely muted but for a pealing guitar riff. It sounds like the reference track was Buffalo Springfield’s "For What It’s Worth," or like, the Mountain Goats.

The hit here is "Downtown," which features three legitimate rap pioneers—Melle Mel, Kool Moe Dee, and Grandmaster Caz—and passionate vocal theatrics from Foxy Shazam’s Eric Nally. Macklemore’s verses are trivial—the opening verse details his attempt to purchase a Moped—but there’s an appealing breeziness to his low-stakes ribbing. The rap O.G.s aren’t given much to do, acting as a chanting Greek chorus and flexing in the video, but their presence gives the song the feeling of an event and allows Macklemore to show he knows and respects his history. (According to Kool Moe Dee, it was Big Daddy Kane who brokered the collaboration.) "Downtown" is a Broadway song, basically—rap for people who loved Hamilton. I hear it and imagine parades, streamers, the Super Bowl half-time show they will probably someday play.

Macklemore is also a skilled mimic. He presses hat to heart when Chance the Rapper is around, spits with cocksure nostalgia around KRS-One and DJ Premier, does budget OG Maco-flow trading lines with YG on "Bolo Tie." On album highlight "Need to Know," Chance delivers a thoughtful verse about the pitfalls of fame—being alienated from the white girls who "call me nigga at my show," feeling the pressure to strip the spirituality out of his music and "just leave the cool parts." (Meanwhile, Macklemore offers hashtag rap in the guise of self-awareness: "I only think about my worth, I only think about my come up/ Capitalism.") It’s the opposite of Chance’s stint on Kanye’s "Ultralight Beam," where he exclaimed "I’m just having fun with it!" But Chance isn’t here to have fun, because Macklemore is so granite-faced on the serious songs that his guest stars have no choice but to match his mood.

"Fun" is reserved for songs like "Dance Off" (in which Idris Elba challenges you to a dance off) or "Brad Pitt’s Cousin" (in which Macklemore boasts that "every white dude in America went to the barbershop: 'Give me the Macklemore haircut'"). That said, it isn’t always easy to tell when Macklemore is trying to be fun, or when we are having fun at his expense. "Let’s Eat" is presumably about our collective body image issues, but the jokiness prevents it from getting a foothold. Macklemore would not be the first rapper to alternate between goofiness and gravitas, but the gulf between sober analysis of Oxycontin abuse and white privilege, and the "DEEZ NUTS" jokes is just too wide. If he’s serious about wanting to "start conversations and change the way that we think and we feel," he needs to sound as comfortable serving wisdom as he does shooting Sandler-esque wisecracks.

The trumped-up portentousness of "White Privilege II" is still difficult to digest. It’s a messy explainer of his still-forming politics, a Facebook status come to life. His heart is in the right place, but it’s hard to justify on musical terms. He doesn’t deserve a free pass for being well-intentioned, of course. But "White Privilege II" is different from, say, Brad Paisley and LL Cool J’s "Accidental Racist," another race-focused song with its heart in the right place that nevertheless missed the mark because it made no attempt to examine its founding premises. ("If you don’t judge my gold chains, I’ll forget the iron chains" is not a fair trade.) Instead, Macklemore is laboring to show us, brick by awkwardly-rapped brick, how he laid the foundation of his new ideology. It isn’t a link to a Wikipedia page—it’s the whole article. As a song, it’s not great. As an endeavor, it’s hard to be snide about. His credibility regarding his intellectual growing pains is the most essential part of his music, even as it’s also the part that makes him seem doe-eyed and naive.

In other words: Do you want to argue that more public discussion of systemic power imbalances is a bad thing? More than one person I follow on Twitter expressed surprise that anyone needs white privilege explained to them, but Donald Trump has won three presidential primaries and counting, so maybe Macklemore has a better bead on the country than some are willing to admit. We can also dispense with the take that his motivation in writing songs like "White Privilege II" is cynical, because solemnly intoning about white supremacy is insistently anti-commercial, and not likely to endear him to radio markets that think Beyoncé hates the cops. It would have been much, much easier to record an album of "Thrift Shop" sequels; I’m sure at least one record executive suggested it.

Like Macklemore, This Unruly Mess I’ve Made is nowhere near as bad as its detractors would like it to be. It’s an occasionally inspiring, often corny rap album made for winning Grammy nominations and waking the hearts of the unwoken. The sum of this is sometimes appealing, though frustrating, if only because you’d like to imagine a world where Macklemore was not counted on to inject a dose of political consciousness into our daily proceedings. I’m thinking about Kendrick Lamar, and what he said months after Macklemore’s public apology. "Yeah, I think it was uncalled for," he opined. "But I think, for confirmation from the world, he probably felt like he had to put it out there, which he didn’t need to do... I don’t take nothin’ away from him anyway 'cause I know where his heart is at. He cool."