3. Drake – $39.5 million The Canadian import clocks the highest Cash Kings finish of his young career, thanks mostly to earnings on the road, where he played 50 dates during our scoring period with a nightly average gross of nearly $1 million. Also padding Drake’s coffers: gold-certified surprise record If You’re Reading This It’s Too Late and endorsements for Sprite and Nike. 4. Dr. Dre – $33 million Selling Beats to Apple earned him $620 million on last year’s list, the top annual payday of any musician, ever. This year Dre’s haul mostly comes from royalties and smaller Apple checks.