Broadimage / REX / Shutterstock / Rex USA 1 / 50
Broadimage / REX / Shutterstock / Rex USA 1 / 50

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 Las Vegas, Curb Your Enthusiasm, General Hospital and Entourage and a parts in The House Bunny and Scary Movie 4 and 5. Wilkinson left Hefner in late 2008 and announced her engagement to Eagles receiver Hank Baskett. She immediately spun the new relationship into TV fodder on Kendra (2009-11) and Kendra On Top (2012-14). She married Baskett in June 2009 and they had son Henry in December 2009 and daughter Alijah in May 2014. She competed on Splash, Dancing With The Stars and I’m A Celebrity, Get Me Out Of Here! In 2014, amid rumors of his infidelity, their marriage was on the rocks, but they’ve appeared happy in 2015, hitting ski slopes as a family in January and signing on for Marriage Boot Camp.