"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.