Macklemore

Thrift shop fur coats, huge horn riffs, and four Grammys swept right out from under rap royalty. Macklemore broke the charts wide open alongside producer Ryan Lewis in 2012, proving you didn't need a major label to score a diamond record. Love him or roll your eyes at the earnestness, you definitely know the words to his biggest hooks.

He has never backed down from doing things his way. These days, he splits his time between making solo records, speaking openly about his recovery journey, and jumping straight into political flashpoints. Ben Haggerty refuses to fade into a nostalgic 2010s footnote.