Macklemore & Ryan Lewis

In a 2016 interview with Apple Music, Seattle rapper Macklemore recounted the moment when, at age 17, he realised his life’s true calling. 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. 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. Upon connecting with producer Ryan Lewis in 2009, Macklemore finally acquired the megaphone that allowed him to project his big ideas to the masses. 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. Success has only intensified Macklemore’s conflicted relationship with rap: On his 2017 solo single, “Good Old Days”, he looks back fondly at his early years as an unknown MC trying to break into the game; however, the track’s elegant, ascendant piano chords and heartrending Kesha cameo suggests he’s grown evermore accustomed to playing the crowd-pleasing pop star.