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1990s / Anna Kournikova
Ah, yes...adorable Anna Kournikova! She was the Russian tennis goddess with the incredible good looks and the incredibly mediocre record. Anna reached the semifinals of Wimbledon in 1997 at the age of 16--and never did much after that. Despite never having won a professional title in singles, Anna was always among the tour's leading earners in endorsements. (Gee, I wonder why.) She famously dated Russian the two hockey stars pictured here, Pavel Bure and Slava Fedisov. Both experienced declines in their careers after dating Anna. ![]()
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