How Kendra Wilkinson went from Playboy to TV reality fame

About

Birthplace: San Diego, California
On her roots: I was living day by day, working as a dental assistant, living on EasyMac and SpaghettiOs. I didn't know where my life was going.
Words to live by: I don't want negative energy. I want everything positive around me.
On Hugh Hefner: Hef saved me, basically. He kind of took my life and made it into something.

Born and raised in Clairemont, a suburb of San Diego, Kendra Wilkinson was working as a dental assistant and “living on EasyMac and SpaghettiOs,” when a friend wisely suggested she should model. The sports fanatic and tomboy took those words to heart and immediately started working as a glamour model. Soon enough, her winning face, body and personality won her a job as a Painted Lady at Hugh Hefner’s 78th birthday party. A few days later, Hef called her personally and asked her to be his girlfriend, and Kendra moved in to the Mansion. “Hef saved me, basically,” Wilkinson told Playboy. “He kind of took my life and made it into something.”

Soon she was vaulted to reality TV stardom. Wilkinson starred on The Girls Next Door with fellow girlfriends Holly Madison and Bridget Marquardt for five years, and lived at the Mansion until 2009, when she moved in with her then-fiancé, Hank Baskett, which was captured in her own spin-off reality show, Kendra. (There were no hard feelings – the pair was married at the Mansion, and Kendra refers to Hef in jest as her son’s godfather.) The two welcomed a child (Hank Baskett IV) in 2009, a second (Alijah Mary Baskett) in 2014 and filed for divorce in 2018. Kendra then starred in another reality series, Kendra on Top.

Since leaving the mansion, Wilkinson published a memoir titled Sliding Into Home. Then came the sex tape. Taking the good with the bad, Kendra persisted, launching her reputation as a reality star to meteoric heights, having appeared on: Dancing with the Stars, Celebrity Wife Swap, I’m a Celebrity...Get Me Out of Here! and Marriage Bootcamp: Family Edition.

Of all Kendra’s accomplishments, professional and otherwise, she still fondly remembers her time with Hef, Playboy and the eye-popping pictorial that featured the sports fanatic in nothing but a itsy bitsy San Diego Chargers jersey, posed alongside Madison and Marquardt in equally tiny cheerleader uniforms. “This is my dream photoshoot,” she says. “I’m doing a Heisman pose, naked except for a Chargers jersey.” Score!