63. Jenny McCarthy
Wifey Of: Brian Urlacher, Chicago Bears (NFL)
Occupation: TV Personality, Actress
In the mid-to-late 1990s, nobody was hotter than Jenny McCarthy. She was Playboy's 1994 Playmate of the Year, became the host of the popular MTV show Singled Out in 1995, and landed her first major film role in BASEketball in 1998. She has also authored an astonishing nine books.
While her star may have faded a bit, McCarthy still made headlines in April of this year when she began dating Chicago Bears star Brian Urlacher. In August, the same month she made her glorious return to the cover of Playboy, McCarthy announced that the pair had decided to break off their relationship.