Enrique Iglesias and Anna Kournikova
The next couple on our list, now worth $150 million, met on the set of Iglesias' 2001 music video hit "Escape" and have been together since. They welcomed three children into their FamilyFamily: a set of twins and another daughter three years ago.
Kournikova retired from tennis in 2003 due to back problems and has since engaged in television and Global Ambassador work. In an interview, Iglesias emphasized their Family's privacy, adding, "...you really never know where life is going to take you and what can happen."
