Dr. Dre — Beats by Dre

Dre sold Beats Electronics to Apple for $3 billion in 2014 — the largest acquisition in Apple's history. His personal cut was an estimated $750 million after taxes. To put that in perspective, his entire music career — NWA, The Chronic, 2001, producing for Eminem and 50 Cent — earned him roughly $100 million over 30 years. One headphone brand made him 7.5x what three decades of legendary hip-hop production did. The night the deal closed, he posted a video with Tyrese: "The first billionaire in hip-hop. Right here from the motherf***ing West Coast."