Kendra Wilkinson
Raised by her Eagles' cheerleader mom and her grandmother after her father left when she was 4, Kendra Wilkinson exceled at softball and worked part time as an office assistant while trying to get her modeling career off the ground. In April 2004, she was hired to attend Hugh Hefner's 78th birthday after a photographer submitted her photo. Hefner asked her to be his third girlfriend alongside Holly Madison and Bridget Marquardt and the trio's relationship with the Playboy CEO was chronicled on E's hit show The Girls Next Door from 2005 to 2009. It led to guest spots on
