21. Mariah Carey
Wifey Of: Derek Jeter, New York Yankees (MLB), Tom Brady, New England Patriots (NFL)
Occupation: Singer, Actress
Before Nick Canon and Wild 'N Out had ever hit the MTV airwaves, Mimi had taken a spin down the road to WAGdom. She began dating New York Yankees captain Derek Jeter in 1997 when she may have still been married. Once she finalized her divorce, however, the thrill was gone from the relationship and the couple split in 1998, citing the constant media scrutiny as a driving force. Rumors surfaced in 2002 linking Carey with New England Patriots quarterback Tom Brady after they were seen bumping and grinding on a Boston dance floor, but fortunately for Brady these reports were deemed unfounded.