40. Tyra Banks
Wifey Of: Chris Webber, Detroit Pistons (NBA)
Occupation: Model, TV Personality
Before she was a media mogul and a Harvard Business School attendee, Tyra Banks was a simple talk show host and former model. During that period, she began a relationship with former college and NBA star Chris Webber, and the couple ended up dating from 2001 to 2004. Tyra even had one of her often-seen crying breakdowns on her show when discussing a "former boyfriend" (ostensibly Webber) with one of Webber's teammates and his wife. Powerful, powerful stuff. Webber has since married a different long-time girlfriend, though, so he was clearly unaffected by this emotional outburst from his former squeeze.