Questlove was drumming for his dad’s band by the time he was 12. Since then, he founded a prolific hip-hop band with his high school classmate, became a chronicler of popular music history, came into his own as a documentary filmmaker, and more. So why does he still feel insecure about being an artist? Questlove talks with Marc about the origins of The Roots, the decision to become a late night house band, winning an Oscar right after the infamous slap, and why he had an underlying motivation for making his recent documentary about Sly Stone.