3. Cindy Crawford - $100 millionCindy Crawford's modelling career left behind a legacy of 'the mole' as fans and tweens throughout the 80s penciled in their own faux-beauty-marks in order to channel Crawford's legendary beauty. Cindy dropped out of Northwestern University to pursue modelling and the decision helped Crawford become one of the most successful super models of the 80s-90s. Crawford was a familiar face to the big name editorials --- Vogue, W, People, Harper's Bazaar, Elle, Cosmopolitan, and Allure. By 1998 a tally showed that Cindy Crawford had made over 400 appearances in those magazines. [Photo via] Turn from Model to Mogul: Cindy Crawford was one of the first models to be coined as a "modelpreneur." Cindy Crawford collaborated with furniture retailers, J.C Penney, Raymour & Flanigan, Rooms to Go, and Art Van to help market her own line of budget furniture called "Cindy Crawford Home Collection." The woman behind the famous mole also has her own line of skin care, Meaningful Beauty, which produces anti aging products for women. She is also on the celebrity board of the Ronald McDonald House Charities, as well as the Honorary Committee of the California Wildlife Center.