This dude has been speaking his truth since he was writing clown songs for college kids. I was one of those kids. I remember getting into his EPs on random music blogs when I was studying abroad back in 2011. I was in an Atmosphere phase, Macklemore and Ryan Lewis seemed like the millenial white compliment to that sound. I didn’t think he was a Billboard Top 40 artist then, but felt like there was a goofiness and honesty to his music much like Childish Gambino at the time.

Which is how I think of him. His authenticity comes from being a cheesy kid from Seattle. music.youtube.com/watch

^This is tribute song he wrote for the late Seattle Mariners announcer Dave Niehaus. For anyone outside Seattle, you could say “who cares?”. But as a fan of the mid-market San Diego Padres, I can identify with a rare and incredible playoff moment that isn’t a championship. “My Oh My” captures that and so much more: a nostalgia for sports, community and how embedded that emotional investment is in childhood.

Moving to the present day, that spirit hasn’t changed much. If you actually listen to his “Free Palestine” speech it is not a rage-fueled shpeal. It’s not even reminiscent of his “Hind’s Hall” track from two years ago (to give some context for how long Mackelmore has been outspoken). It’s about recognition of harm and liberation, and as always with Macklemore, love.

I’ve seen the criticisms from media networks bring up Macklemore wearing that ridiculous groucho costume in 2014 that should rightly be condemned as depicting a racist Jewish caricature. But no one bothers to acknowledge he apologized quickly, which I encourage you to read his words. For where we are in 2026, it’s pretty benign.

He’s nothing if not consistent with pining for equality and love for all peoples, things that resonated in the 2000s and 2010s. So it’s a little astounding for Ed Sheeran, a longtime friend of Macklemore’s, to kick him off the tour after he was clearly fine with him speaking and doing his thing as his opener. The rest of the fallout has been widely covered, I don’t need to rehash what you’ll likely see on the algo feeds we consume each day.

But I think understanding even a modicum of Macklemore’s decades-long history and expression shows many things: the cowardice of Ed, the power of money (Kraft’s ultimatum to cancel Ed’s tour), and the reaction being so swift against Sheeran and Kraft that both have already donated millions to humanitarian aid in the Middle East.

So, Macklemore or Mackleless? In 2026, the answer appears to be the former.