His stage name originated from his childhood; it was the name of his made-up superhero. Since 2000, he has independently released one mixtape, three EPs, and four albums. He has significantly collaborated with producer Ryan Lewis as Macklemore & Ryan Lewis.

Macklemore and Ryan Lewis’s single “Thrift Shop” reached number one on the U.S. Billboard Hot 100 in 2013. The single was soon dubbed by Billboard as the first song since 1994 to top the Hot 100 chart without the support of a major record label, although Macklemore, in a slightly unusual recording contract, pays a nominal percentage of sales to use Warner Bros. Records’s radio promotion department to push his singles. Their second single, “Can’t Hold Us”, also peaked at number one of the Hot 100 Chart, making Macklemore and Lewis the first duo in the chart’s history to have their first two singles both reach the peak position. Macklemore and Lewis released their debut studio album The Heist on October 9, 2012, which charted at number 2 on the U.S. Billboard 200. The pair won four Grammy Awards at the 2014 ceremony, including Best New Artist, Best Rap Album (The Heist), Best Rap Song and Best Rap Performance (“Thrift Shop”). Their second album, This Unruly Mess I’ve Made, was released on February 26, 2016.