In addition to all of the great things that happened in music, especially Hip-Hop, for 2014, there have been some uncomfortable moments. As art parallels life, and life parallels art, America witnessed murders, arrests, protests, actions (and non-actions) and other public issues raise the question of racial equality. In Hip-Hop music, a form of expression created by Blacks and Latinos in the 1970s, now extensively populated, supported, and utilized by Whites, those discussions were also ongoing.

While it’s been nearly 30 years since Blondie was awarded Rap credit for Fab 5 Freddie-name-checking in “The Rapture,” 2014 showed White Rap artists competing strongly on radio, at award shows, and in mainstream representation of this culture rooted in speaking out against oppression of all types. As LL Cool J and Brad Paisely awkwardly released “Accidental Racist,” to some incredibly perplexed reception, Iggy Azalea and Azealia Banks fueled a longstanding social media feud, bringing in everybody from Q-Tip to Action Bronson. Macklemore & Ryan Lewis left the Grammy Awards with arm-fulls of trophies, while Kendrick Lamar went home empty-handed.

Following an emotional discussion on race, rifts, and White Appropriation at HOT 97 earlier this week from Banks, Macklmore is Ebro and Rosenberg’s next guest on the station’s morning show.

In an hour-long discussion, Macklemore, a decade-plus veteran Hip-Hop artist opens up about his own views on race, the White Privilege he has personally experienced in his platinum skyrocket to fame, and how he personally messed up after the Grammy’s.

Whether you agree with Macklemore (or Ebro, or Rosenberg, for that matter), this dialogue is thoughtful, rare, and in the case of the Seattle, Washington superstar, not at all self-aggrandizing. Rather than paint himself as a social martyr, the artist born Ben Haggerty simply wants to break the ice, and take the risks to contribute to the discussion on race, rather than dust history or facts under the rug.

Per usual, Ebro pushes with some direct, penetrating questions, starting right away at the 3:00 mark. Macklemore immediately agrees that his success has been supported by his “safe” image (11:30), which he feels is related to his race, style, and approach. The discussion leads to the markets and audiences that supported the artist with his 2012 release, The Heist, and how some radio stations embraced him that may not embrace peers such as J. Cole, Kendrick Lamar, or even Drake. Mack’ states the following, “The privilege that exists in the music industry is just a greater symptom of the privilege that exists in America.”

Moreover, Macklemore looks at his hit “Same Love,” the song that championed Gay Rights, and admits that he was not the first artist to challenge those notions. Released a year to the month after Murs and Ski Beats’ “Animal Style,” Macklemore declares, “I got put in that hero box,” which only added to his profile, mystique, sales, and accolades. Coming back to his image and distributed message, the longtime DIY MC seemingly admits that he’s won a game on an anything-but-level playing-field.

The discussion then focuses on Azealia Banks’ recent interview (28:00). Revealing that he watched the discussion several times, Mack’ removes himself from any of the derogatory remarks made about other artists, but shows solidarity to the Harlem, New Yorker who was signed to Interscope Records before being abruptly released from her contract. Mack’ recognizes the frustrations and anger of one of his peers, and hears her out. Discussing Jazz and Black Art at large, Macklemore claims to understand the sensitivity surrounding White artists rapping, or making work that’s competing with Black, Latino, and other minorities. By the 36:00 mark, the MC states that he believes there needs to be more emphasis on history, especially on White people living, working, or making Hip-Hop surrounding its origins and expressions. Pointedly, he adds, “What I’m saying is not to appease Black people. What I’m saying is the truth.”

Macklmore is not above mistakes, he says. While Rosenberg recalls his own criticism of Public Enemy’s Chuck D, claiming that it would not have been an issue of Rosenberg was not White, Macklemore focuses on his own 2014 faux-pas. Regarding the Instagrammed text message to Kendrick Lamar following the Grammy Awards, Mack’ says, “I made a mistake. A lot of fear was going into that moment.” Explaining that he learned of the wins before the show’s start, Macklemore considered addressing his views on stage, but didn’t. Instead, he used social media. “I betrayed Kendrick’s trust, and that’s wack.” Rather than simply reach out to his friend, he made the moment public, making himself seem to be the cultural benefactor in the eyes of some. He also bemoaned using the word “rob” given the strong racial connotations, both musically and socially.

However, Macklemore is also a B-Boy. After much has been said, by Kendrick, by media, and others, the Warner Bros.-distributed artist touted, “Don’t get it twisted, I wanted to win some Grammy’s…I think we made a great album.”

At the 52:00 mark, Heads can hear Macklemore’s thoughts surrounding this year’s Grammy Award winners, and the albums he likes. Additionally, he reacts to a line in J. Cole’s new album, 2014 Forest Hills Drive, that name-checks him.

Outside of race, this interview sheds light (in small, lucid moments) on Macklemore’s first ever vacation, his sobriety, and the exclusivity he and Ryan Lewis are trying to uphold as they move into a 2015-planned follow-up to The Heist.

What’s your takeaway from this no holds barred interview?

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