19. Anna Kournikova
Here's a success story based on the triumph of sex appeal over the service winner. Blessed with the looks like a Bond Girl, Kournikova has been an endorsement machine, hawking products all over the world and garnering off-the-court platitudes such as one of People magazine naming "50 Most Beautiful People." While she did win a couple of Grand Slam doubles titles and was a consistent member of the Top 20 before injuries, she has never won a professional singles tournament. Never had an athlete achieved more fame for her looks.