Cindy Crawford

The mole. The Pepsi commercial. The MTV House of Style. Crawford was the first supermodel who understood that modeling was just content, and content could be distributed everywhere. Her 1992 Pepsi Super Bowl ad was watched by 133 million people. She turned that visibility into a $100+ million empire: Meaningful Beauty skincare, a furniture line, and savvy real estate investments. Her daughter Kaia Gerber is now a top model, making the Crawfords fashion's most successful dynasty that doesn't share a last name with Kardashian.