88. Carrie Prejean
Wifey Of: Kyle Boller, Oakland Raiders (NFL)
Prejean stirred up quite a bit of controversy during the 2009 Miss USA pageant, where she announced to Perez Hilton (and the rest of the world) that she did not approve of gay marriage. Her answer caused her to finish runner-up in the competition and brought significant negative attention upon the then-20-year-old.
She subsequently finished runner-up to Tara Reid in hooking up with former NFL quarterback Kyle Boller. While this penchant for second place would seemingly doom Prejean, she actually has recovered nicely; she and Boller are now married and have a child, and she settled her lawsuit against the Miss California USA pageant.