With producer Ryan Lewis, Macklemore saw huge success with The Heist, an album that was released in 2014. 

Then two years later, they scored a hit song with "Downtown," the first single off their LP This Unruly Mess I've Made.

Macklemore spoke about that period of time with Apple Music's Zane Lowe and said he was miserable. 

“Yeah, it was dark. It was a dark, very challenging era," he admitted, per AllHipHop. "That era was tough, man. It was all the criticism, all the expectations, all the accolades, all the love, all the hate, everything at once. And I spent my entire life being an underground rapper. All of a sudden that changed."

“And there was an era in that period where it was like, ‘Wait, hold on. You guys remember what I’ve done? You guys remember where I came from?’ And it was like, ‘No, my little sister likes your music now. This is wack.’ And in that moment, it was really intense ... You’re up for judgment from the world, and no one tells you how to handle that. And here we are at the top of the world and I have no idea what the f*ck I am doing."

Macklemore's next project, titled Ben, drops on Friday, March 3.