Wifey Of: Pavel Bure, New York Rangers (NHL), Sergei Fedorov, Detroit Red Wings (NHL)
Occupation: Professional Tennis Player, Model, TV Personality

Even though she never managed to win a singles title in her time as a professional tennis player, Kournikova has never lacked her share of fans. She was initially linked to former Detroit Red Wings star Sergei Fedorov, but in 1999 she began seeing another famous hockey player, "the Russian Rocket" Pavel Bure. A year later, the two became Russian media stars (yes, those do exist) when they allegedly got engaged despite Kournikova being just 18 at the time. It's also worth noting that one can apparently order an "Anna Kournikova" (a White Russian with skim milk) at his or her favorite drinking establishment, which may end up being this bombshell's lasting legacy.