19. Cindy Crawford and Rande Gerber

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It’s been 20 years since Cindy Crawford and former model Rande Gerber have been married. Her husband is now a businessman, and together with Cindy, they have two children who are also into modeling. Gerber is now into restaurants and bars, and even started a tequila company with George Clooney, called Casamigos!
Let’s check out another CEO and his beautiful supermodel at #14.