Their 2012 self-released debut, The Heist, crashed the Billboard Top 5 and scooped up four Grammys thanks to a string of unlikely crossover hits-like the sax-squawked anti-luxury anthem “Thrift Shop” and the pro-LGBTQ ballad “Same Love”-that betrayed his love of pre-millennial hip-hop sounds while interrogating some of the genre’s problematic materialist and homophobic tendencies. Upon connecting with producer Ryan Lewis in 2009, Macklemore finally acquired the megaphone that allowed him to project his big ideas to the masses. But during those DIY days, Macklemore developed a reputation for intense introspection and keen cultural observations-on his 2005 track “White Privilege,” he examined not only the gentrification of hip-hop from black street music to commercial commodity but also his own complicity in that process as a white MC. Hip-hop, he said, was “my means of trying to figure out who I am, and to figure out my truth, and look at society and get closer to a connection to something much bigger than myself.” It would take some time for him to make that greater connection: The MC born Benjamin Haggerty in 1983 dropped his first mixtape in 2000 and spent the next decade doing the underground grind.

In a 2016 interview with Apple Music, Seattle rapper Macklemore recounted the moment when, at age 17, he realized his life’s true calling.

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