Macklemore explores racism and hip-hop in a new song called White Privilege II, rapping about a white person's position in society with black people fighting injustice and even namechecking Iggy Azalea for appropriating black culture, along with himself.
The track, released Friday, is close to nine minutes long and starts with the Grammy-winning rapper at a march in support of the Black Lives Matter movement.
"I wanna take a stance because we are not free, and I thought about it, we are not we," he raps on the song, released with musical partner Ryan Lewis.
"Am I in the outside looking in? Or am I in the inside looking out?" Essence magazine entertainment director Cori Murray said she appreciated Macklemore's honesty.
"I don't think there's an easy answer, and I think that he really did just say very plainly, ... 'I know I'm appropriating black culture, but I'm trying to do it in the most authentic way,"' Murray said.
Macklemore & Ryan Lewis released the song the week Spike Lee, Will Smith, Jada Pinkett Smith and others said they were skipping the Academy Awards because of two straight years of all-white acting nominees.
The Seattle-based duo's website says the song "is the outcome of an ongoing dialogue with musicians, activists, and teachers within our community in Seattle and beyond."
Macklemore namedropping Azalea and other singers accused of appropriating black culture has gotten attention on social media.
"We wanna dress like, talk like, walk like, dance like, but we just stand by, we take all we want from black culture, but do we show up for black lives?" he raps.
Azalea, known for the hits Fancy and Black Widow, responded on Twitter after a fan pointed the song out to her.
"He shouldnt have spent the last 3 yrs having friendly convos and taking pictures together at events etc if those were his feelings," Azalea wrote.
Hot 97 radio personality Peter Rosenberg said the diss was just Macklemore being honest.
"You can take it as an all-out insult, as Iggy did ... but that's appropriate, it's done factually," said Rosenberg, who co-hosts "Ebro in the Morning" and played White Privilege II early Friday during the radio show.
Macklemore & Ryan Lewis became a success when they independently released their 2013 debut The Heist, which featured the multi-platinum No. 1 hits Thrift Shop and Can't Hold Us.
The success also brought them drama: After submitting their songs and album to the rap categories at the Grammys, they were kicked out of the category by the rap committee, though the decision was later overruled.
They went on to win Grammy awards in 2014 for best new artist, rap performance and rap album, besting critical darling Kendrick Lamar. Afterward, Macklemore said Lamar should have won best rap album.
The duo returned to music last year with the platinum single Downtown and will release a sophomore album, This Unruly Mess I've Made, next month.