Anna Kournikova, 40 – Moscow, Russia

Anna Kournikova may be better known for her work as a television personality than for her tennis career. But this is not to say that she wasn’t a notable player in the sport. In fact, she achieved immense success and was crowned the world’s No. 1 player in doubles.

Teaming up with Martina Hingis, she won two Grand Slam titles in Australia and two WTA Championships. However, Kournikova retired in 2003 and decided to divert her talents elsewhere. In 2011, she worked as a trainer on NBC’s “The Biggest loser.” In 2020, Kournikova and Enrique Iglesias welcomed their third child together.